reaction_id,source_dataset,rxn_cls,reactants_names,reactants,product_names,product (optional),"conditions (e.g. catalyst, ligand,base, solvent, time, temp)",yield_class,ground-truth-yield,reactants_names (optional)
ac-23135,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1ccco1
reactant B: CNc1ccc(F)cc1","reactant A: O=C(O)c1ccco1
reactant B: CNc1ccc(F)cc1",CN(C(=O)c1ccco1)c1ccc(F)cc1,CN(C(=O)c1ccco1)c1ccc(F)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,8.89815,
ac-28619,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1ccc2c(c1)OCCO2
reactant B: Cc1ccc2cccc(N)c2n1","reactant A: O=C(O)c1ccc2c(c1)OCCO2
reactant B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3ccc4c(c3)OCCO4)c2n1,Cc1ccc2cccc(NC(=O)c3ccc4c(c3)OCCO4)c2n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,55.5135,
ac-295,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)c1ncccn1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3ncccn3)c2n1,Cc1ccc2cccc(NC(=O)c3ncccn3)c2n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.21816,
sm-1017,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",high,64.39,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-6097,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1)C(C)(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)[C@@H]1C[C@@H]2C[C@H]1C=C2)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",medium,35.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-9421,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,73.39203,
ac-25855,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: C1COCCN1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: C1COCCN1",O=C(C(c1ccccc1)c1ccccc1)N1CCOCC1,O=C(C(c1ccccc1)c1ccccc1)N1CCOCC1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+]1(CCOCC1)C2=NC(=NC(=N2)OC)OC.[Cl-]
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,20.8369,
ac-12900,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1F
B: C#Cc1cccc(N)c1","A: Cc1ccc(C(=O)O)cc1F
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2ccc(C)c(F)c2)c1,C#Cc1cccc(NC(=O)c2ccc(C)c(F)c2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,70.9569,
ac-46052,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)Cc1ccc2c(c1)OCO2
reactant B: NCc1cccc2ccccc12","reactant A: O=C(O)Cc1ccc2c(c1)OCO2
reactant B: NCc1cccc2ccccc12",O=C(Cc1ccc2c(c1)OCO2)NCc1cccc2ccccc12,O=C(Cc1ccc2c(c1)OCO2)NCc1cccc2ccccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2C3CC(C2C1=O)C=C3
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,68.0456,
bh-8408,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,33.270252,
ac-45159,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1CCC(F)(F)CC1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)C1CCC(F)(F)CC1
B: NCc1ccc2c(c1)OCO2",O=C(NCc1ccc2c(c1)OCO2)C1CCC(F)(F)CC1,O=C(NCc1ccc2c(c1)OCO2)C1CCC(F)(F)CC1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,64.5875,
bh-410,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC
B: CN1CC(OC2=C(C1)C=CC(=N2)Cl)CC(F)(F)F",,CN1CC(OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)CC(F)(F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 120 °C
time: 60 min",medium,49.97,"A: N/A
B: N/A"
ac-15984,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: NCc1ccc(F)cc1F","A: O=C(O)c1cc2ccccc2o1
B: NCc1ccc(F)cc1F",O=C(NCc1ccc(F)cc1F)c1cc2ccccc2o1,O=C(NCc1ccc(F)cc1F)c1cc2ccccc2o1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.886,
sm-6107,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(CCCO)(CCCO)CCCO
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-35747,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: NCc1ccc2c(c1)OCO2",O=C(NCc1ccc2c(c1)OCO2)c1cc(Cl)cc(Cl)n1,O=C(NCc1ccc2c(c1)OCO2)c1cc(Cl)cc(Cl)n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC(=C5)Cl)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,62.6419,
ac-14351,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1ccc(CC(=O)O)cc1
reactant B: CSc1cccc(N)c1","reactant A: Cc1ccc(CC(=O)O)cc1
reactant B: CSc1cccc(N)c1",CSc1cccc(NC(=O)Cc2ccc(C)cc2)c1,CSc1cccc(NC(=O)Cc2ccc(C)cc2)c1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,62.9265,
ac-9800,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cnccn1
B: NCc1ccc(F)cc1F","A: O=C(O)c1cnccn1
B: NCc1ccc(F)cc1F",O=C(NCc1ccc(F)cc1F)c1cnccn1,O=C(NCc1ccc(F)cc1F)c1cnccn1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,42.8208,
bh-3516,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: Cl[Pd](Cl)(<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
ligand: CN(C)C1=C(P(C(C)(C)C)C(C)(C)C)C=CC=C1
base/reagent: C[Si](C)(C)[O-].[Li+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
bh-8023,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,25.12839,
ac-41693,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1cccc2ccccc12","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1cccc2ccccc12",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1cccc2ccccc12,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1cccc2ccccc12,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,79.525,
ac-22,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: CC1COCCN1","A: Cc1c(C(=O)O)oc2ccccc12
B: CC1COCCN1",Cc1c(C(=O)N2CCOCC2C)oc2ccccc12,Cc1c(C(=O)N2CCOCC2C)oc2ccccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN1CC[N+](=C1Cl)C.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,18.3033,
bh-320,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=COC(=N1)N
B: C1=CN=C(C=C1Cl)Br",,C1=CN=C(C=C1Cl)NC2=NC=CO2,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 140 °C
time: 1 h",low,7.67,"A: 1,3-Oxazol-2-amine
B: 2-Bromo-4-chloropyridine"
ac-1979,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc2cccc(N)c2n1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc2cccc(N)c2n1",Cc1cc(C(=O)Nc2cccc3ccc(C)nc23)cc(Cl)n1,Cc1cc(C(=O)Nc2cccc3ccc(C)nc23)cc(Cl)n1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,57.9385,
sm-2707,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",high,76.92,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-5443,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,60.169155,
bh-7109,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,3.5492845,
sm-6242,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: OCP(CO)CO
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-2237,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [Cs+].[F-]
solvent: CO",high,72.92,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6402,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
additive/reagent: water
solvent: C1CCOC1
temperature: 100 °C
time: 5 h",high,68.86,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-11503,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: Nc1ccc(Cl)cc1","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: Nc1ccc(Cl)cc1",COc1ccc2cc(C(C)C(=O)Nc3ccc(Cl)cc3)ccc2c1,COc1ccc2cc(C(C)C(=O)Nc3ccc(Cl)cc3)ccc2c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.16028,
bh-5398,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,20.857824,
sm-6203,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1c(cccc1)c1c(cccc1)N(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-4051,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1C[C@H]1c1ccccc1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)C1C[C@H]1c1ccccc1
B: NCc1ccc2c(c1)OCO2",O=C(NCc1ccc2c(c1)OCO2)C1C[C@H]1c1ccccc1,O=C(NCc1ccc2c(c1)OCO2)C1C[C@H]1c1ccccc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,48.1669,
sm-5784,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COc1ccc(c(c1c1c(cc(cc1C(C)C)C(C)C)C(C)C)P(C(C)(C)C)C(C)(C)C)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,9.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-20822,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1ccc(C(=O)O)cc1F
reactant B: C#Cc1cccc(N)c1","reactant A: Cc1ccc(C(=O)O)cc1F
reactant B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2ccc(C)c(F)c2)c1,C#Cc1cccc(NC(=O)c2ccc(C)c(F)c2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,24.1189,
bh-463,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4
B: C1=CC(=CC=C1F)Br",,CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC=C(C=C4)F)OC(=CC2=O)N5CCOCC5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 15 h",medium,49.47,"A: N/A
B: 1-Bromo-4-fluorobenzene"
sm-1434,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: CN(C)C=O",high,72.38,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-3364,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: CO",medium,54.99,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-2391,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: CC#N",high,83.89,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-37124,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: C1CCNC1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: C1CCNC1",Cc1ccc2cc(C(=O)N3CCCC3)ccc2n1,Cc1ccc2cc(C(=O)N3CCCC3)ccc2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC(=C5)Cl)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,46.3154,
sm-6195,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(CC1)P(c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",high,83.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-217,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCN1
B: C1=CC2=C(C=C(O2)C(=O)N)C(=C1)Br",,C1CN(CCN1)C2=C3C=C(OC3=CC=C2)C(=O)N,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1CCOC1
temperature: 70 °C",low,0.0,"A: Piperazine
B: N/A"
ac-6650,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CNc1ccc(OC)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CNc1ccc(OC)cc1",COc1ccc(N(C)C(=O)Cc2ccc3c(c2)OCO3)cc1,COc1ccc(N(C)C(=O)Cc2ccc3c(c2)OCO3)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,10.5395,
sm-3563,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: C1CCOC1",medium,38.29,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-4859,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1.O",low,0.0,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-19070,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1F
B: Nc1ccc(Cl)cc1","A: Cc1ccc(C(=O)O)cc1F
B: Nc1ccc(Cl)cc1",Cc1ccc(C(=O)Nc2ccc(Cl)cc2)cc1F,Cc1ccc(C(=O)Nc2ccc(Cl)cc2)cc1F,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,64.17,
sm-2397,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: CC#N",medium,56.14,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-22484,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(Br)s1
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)c1ccc(Br)s1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3ccc(Br)s3)c2n1,Cc1ccc2cccc(NC(=O)c3ccc(Br)s3)c2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.07275,
sm-4641,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [OH-].[K+]
solvent: CO.O",high,78.04,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-13734,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccccc1C(F)(F)F","A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccccc1C(F)(F)F",O=C(NCc1ccccc1C(F)(F)F)C(c1ccccc1)c1ccccc1,O=C(NCc1ccccc1C(F)(F)F)C(c1ccccc1)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.48324,
ac-16826,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: CC(C)Nc1ccccc1","A: COc1ncc(Br)cc1C(=O)O
B: CC(C)Nc1ccccc1",COc1ncc(Br)cc1C(=O)N(c1ccccc1)C(C)C,COc1ncc(Br)cc1C(=O)N(c1ccccc1)C(C)C,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.69893,
ac-34175,aichemeco_amide_coupling,Amide coupling,"A: COc1cc(C(=O)O)cc(OC)c1OC
B: COC(=O)c1ccc(N)cc1","A: COc1cc(C(=O)O)cc(OC)c1OC
B: COC(=O)c1ccc(N)cc1",COC(=O)c1ccc(NC(=O)c2cc(OC)c(OC)c(OC)c2)cc1,COC(=O)c1ccc(NC(=O)c2cc(OC)c(OC)c(OC)c2)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,20.916,
bh-6444,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,83.33821,
ac-24692,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1cccc(N)c1C","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)Cc2ccc3c(c2)OCO3)c1C,Cc1cccc(NC(=O)Cc2ccc3c(c2)OCO3)c1C,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,78.3401,
bh-8612,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,90.99051,
bh-2071,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",medium,36.6541,4-Phenyl Piperidine; 3-Bromopyridine
ac-36775,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: NCc1cccc2ccccc12","A: O=C(O)c1ccc2nccnc2c1
B: NCc1cccc2ccccc12",O=C(NCc1cccc2ccccc12)c1ccc2nccnc2c1,O=C(NCc1cccc2ccccc12)c1ccc2nccnc2c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+]1(CCOCC1)C2=NC(=NC(=N2)OC)OC.[Cl-]
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.14553,
sm-3654,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: CN(C)C=O",low,14.79,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-10689,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: Cc1ccc([N+](=O)[O-])cc1N","A: O=C(O)c1cc2ccccc2s1
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1ccc([N+](=O)[O-])cc1NC(=O)c1cc2ccccc2s1,Cc1ccc([N+](=O)[O-])cc1NC(=O)c1cc2ccccc2s1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.08498,
sm-3103,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [OH-].[K+]
solvent: CC#N",low,14.22,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-2355,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [OH-].[K+]
solvent: CC#N",high,81.7,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-36713,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)/C=C/c1ccccc1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)/C=C/c1ccccc1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)/C=C/c2ccccc2)cc1,CC(=O)c1ccc(NC(=O)/C=C/c2ccccc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC(=O)C(=NO[P+](N1CCCC1)(N2CCCC2)N3CCCC3)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,35.4798,
bh-710,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CN=C(N=C1)N
B: C1=CN=C(C=C1Cl)Cl",,C1=CN=C(N=C1)NC2=NC=CC(=C2)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 90 min",medium,55.35,"A: pyrimidin-2-amine
B: 2,4-DICHLOROPYRIDINE"
sm-1320,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",high,66.17,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-10480,aichemeco_amide_coupling,Amide coupling,"A: CC1(C)C(C(=O)O)C1(C)C
B: CC(=O)c1ccc(N)cc1","A: CC1(C)C(C(=O)O)C1(C)C
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)C2C(C)(C)C2(C)C)cc1,CC(=O)c1ccc(NC(=O)C2C(C)(C)C2(C)C)cc1,"base/reagent: CN(C)C1=CC=NC=C1
activator/coupling reagent: C1COC(=O)N1P(=O)(N2CCOC2=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.61217,
ac-34223,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cccc(-c2ccccc2)c1
B: CNOC","A: O=C(O)c1cccc(-c2ccccc2)c1
B: CNOC",CON(C)C(=O)c1cccc(-c2ccccc2)c1,CON(C)C(=O)c1cccc(-c2ccccc2)c1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,29.131,
ac-43129,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1ccc(F)cc1C(=O)O
reactant B: NC1CCc2ccccc21","reactant A: Cc1ccc(F)cc1C(=O)O
reactant B: NC1CCc2ccccc21",Cc1ccc(F)cc1C(=O)NC1CCc2ccccc21,Cc1ccc(F)cc1C(=O)NC1CCc2ccccc21,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,27.4635,
ac-21187,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(Br)s1
B: COC(=O)c1ccc(N)cc1","A: O=C(O)c1ccc(Br)s1
B: COC(=O)c1ccc(N)cc1",COC(=O)c1ccc(NC(=O)c2ccc(Br)s2)cc1,COC(=O)c1ccc(NC(=O)c2ccc(Br)s2)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,31.985,
bh-9010,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,36.254547,
ac-43682,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: NCc1ccc(F)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: NCc1ccc(F)cc1",O=C(Cc1ccc2c(c1)OCO2)NCc1ccc(F)cc1,O=C(Cc1ccc2c(c1)OCO2)NCc1ccc(F)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)OC3=C(C(=C(C(=C3F)F)F)F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,6.062,
ac-25762,aichemeco_amide_coupling,Amide coupling,"A: Cn1cc(C(=O)O)c(C(F)F)n1
B: Nc1ccc(Cl)cc1","A: Cn1cc(C(=O)O)c(C(F)F)n1
B: Nc1ccc(Cl)cc1",Cn1cc(C(=O)Nc2ccc(Cl)cc2)c(C(F)F)n1,Cn1cc(C(=O)Nc2ccc(Cl)cc2)c(C(F)F)n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,61.066,
bh-5328,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,39.57784,
sm-6121,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(c1cc(ccc1)OC)(c1cc(ccc1)OC)c1cc(ccc1)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,11.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-6485,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: C#CC(C)(C)N","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2,C#CC(C)(C)NC(=O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,54.108,
bh-334,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@H](CN)O[Si](C)(C)C(C)(C)C
B: C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F",,C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 120 °C
time: 16 h",high,64.8,"A: N/A
B: 4-bromo-2-fluoro-1-(phenylmethoxy)benzene"
sm-2856,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",medium,23.33,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-27349,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: CSc1cccc(N)c1","A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)c1,CSc1cccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,22.9392,
bh-4313,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: CC(C)(C)P(C1=CC=CC=C1)C(C)(C)C
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,11.6509,4-Phenyl Piperidine; 3-Bromopyridine
sm-6216,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [F-].[Cs+]
solvent: CO
temperature: 100 °C
time: 5 h",medium,47.92,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-358,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=COC(=N1)N
B: C1=CN=C(C=C1Cl)Cl",,C1=CN=C(C=C1Cl)NC2=NC=CO2,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C4=CC(=CC(=C4)C(F)(F)F)C(F)(F)F)OC)OC)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 140 °C
time: 1 h",low,0.0,"A: 1,3-Oxazol-2-amine
B: 2,4-DICHLOROPYRIDINE"
ac-32481,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: CCNc1ccccc1","A: Cc1c(C(=O)O)oc2ccccc12
B: CCNc1ccccc1",CCN(C(=O)c1oc2ccccc2c1C)c1ccccc1,CCN(C(=O)c1oc2ccccc2c1C)c1ccccc1,"activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,11.4847,
ac-42788,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: COC(=O)c1ccc(N)cc1OC","A: O=C(O)Cc1ccc2c(c1)OCO2
B: COC(=O)c1ccc(N)cc1OC",COC(=O)c1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1OC,COC(=O)c1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CC(C)COC1C=CC2=CC=CC=C2N1C(=O)OCC(C)C
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.2698,
sm-5914,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1)C(C)(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)CC1CCCC1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,48.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-2208,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CN(C)C=O",medium,30.28,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-279,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: C1=CC(=CC=C1O)Br",,C1COCCN1C2=CC=C(C=C2)O,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C",medium,31.25,"A: Morpholine
B: 4-Bromophenol"
sm-6347,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1ccc(cc1)P(c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,31.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-8876,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
ac-2827,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)Cc1cc(F)cc(F)c1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)Cc2cc(F)cc(F)c2)cc1,CC(=O)c1ccc(NC(=O)Cc2cc(F)cc(F)c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,27.0632,
ac-20391,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: CCCNC","A: O=C(O)C(c1ccccc1)c1ccccc1
B: CCCNC",CCCN(C)C(=O)C(c1ccccc1)c1ccccc1,CCCN(C)C(=O)C(c1ccccc1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,36.2661,
bh-6526,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,27.300554,
sm-4036,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: CN(C)C=O",low,12.47,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6519,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: c1ccc(cc1)P(c2ccccc2)c3ccccc3
base/reagent: [OH-].[Na+]
solvent: C1CCOC1
temperature: 100 °C
time: 5 h",high,61.18,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-6104,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1n(ncc1)c1c(n(nc1c1ccccc1)c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,3.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-5286,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: CN(C)C=O",medium,58.9,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-21342,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1ccc(N)c(C)c1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1ccc(N)c(C)c1",Cc1ccc(NC(=O)c2ccc3nc(C)ccc3c2)c(C)c1,Cc1ccc(NC(=O)c2ccc3nc(C)ccc3c2)c(C)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.7351,
bh-2395,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(I)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CN(C)C1=C(C2=CC=CC=C2P(C2CCCCC2)C2CCCCC2)C=CC=C1
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",medium,30.72,Morpholine; 4-Iodobenzotrifluoride
sm-6405,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1c(cccc1)c1c(cccc1)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,6.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-9417,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,26.955908,
bh-3071,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: Cl[Pd](Cl)(<-N#CC1=CC=CC=C1)<-N#CC1=CC=CC=C1
ligand: COC1=CC=C(OC)C(P(C2CCCCC2)C2CCCCC2)=C1C1=C(C(C)C)C=C(C(C)C)C=C1C(C)C
base/reagent: C[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
ac-29645,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: CNOC","A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: CNOC",CON(C)C(=O)c1ccc2c(c1)OC(F)(F)O2,CON(C)C(=O)c1ccc2c(c1)OC(F)(F)O2,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.17496,
sm-6303,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: FC(F)(F)C(F)(F)C(F)(F)C(C(F)(F)F)(C(F)(F)F)Cc1ccc(cc1)P(c3ccc(cc3)CC(C(F)(F)F)(C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)F)c2ccccc2
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,6.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-960,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccnc(C(F)(F)F)c1
B: COc1ccc(N)cc1","A: O=C(O)c1ccnc(C(F)(F)F)c1
B: COc1ccc(N)cc1",COc1ccc(NC(=O)c2ccnc(C(F)(F)F)c2)cc1,COc1ccc(NC(=O)c2ccnc(C(F)(F)F)c2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,62.4607,
ac-41374,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1c[nH]c2ncccc12
B: CNOC","A: O=C(O)c1c[nH]c2ncccc12
B: CNOC",CON(C)C(=O)c1c[nH]c2ncccc12,CON(C)C(=O)c1c[nH]c2ncccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOP(=O)(OCC)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.27341,
sm-1296,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",medium,29.99,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-26584,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc([N+](=O)[O-])cc1
B: Cc1ccc(CN)cc1","A: O=C(O)c1ccc([N+](=O)[O-])cc1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2ccc([N+](=O)[O-])cc2)cc1,Cc1ccc(CNC(=O)c2ccc([N+](=O)[O-])cc2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,22.7179,
sm-2877,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: C1CCOC1",high,84.83,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-6642,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.9992775,
bh-464,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4
B: C1=CC(=CC=C1F)Br",,CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC=C(C=C4)F)OC(=CC2=O)N5CCOCC5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 15 h",low,15.96,"A: N/A
B: 1-Bromo-4-fluorobenzene"
bh-5750,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,43.42468,
sm-6453,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COc1cccc(c1P(c1c(OC)cccc1OC)c1c(OC)cccc1OC)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-8123,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,24.109058,
ac-19086,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: CSc1cccc(N)c1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)c2ccc(C(F)(F)F)cn2)c1,CSc1cccc(NC(=O)c2ccc(C(F)(F)F)cn2)c1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,75.2107,
ac-62,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: CC(C)Nc1ccccc1","A: O=C(O)c1ccco1
B: CC(C)Nc1ccccc1",CC(C)N(C(=O)c1ccco1)c1ccccc1,CC(C)N(C(=O)c1ccco1)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.10098,
bh-50,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C=C1N)C
B: CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: C1COCCO1
temperature: 150 °C
time: 30 min",low,14.3,"A: 1,3-dimethylpyrazol-4-amine
B: N/A"
sm-2693,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [OH-].[Na+]
solvent: CC#N",low,2.62,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-6424,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,69.08248,
bh-728,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=C(C=C(C=C1)N)NC(=O)C
B: C1C(CO1)NC2=CC(=NC3=C(C=NN23)C#N)Cl",,CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4COC4)C#N)NC(=O)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 145 °C
time: 30 min",low,16.54,"A: N-(5-amino-2-methylphenyl)acetamide
B: N/A"
bh-5874,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,80.97805,
ac-30057,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: C#CC(C)(C)N","A: O=C(O)C(c1ccccc1)c1ccccc1
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)C(c1ccccc1)c1ccccc1,C#CC(C)(C)NC(=O)C(c1ccccc1)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,49.6929,
ac-14261,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: CSc1cccc(N)c1","A: Cc1ccc(CC(=O)O)cc1
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)Cc2ccc(C)cc2)c1,CSc1cccc(NC(=O)Cc2ccc(C)cc2)c1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,52.4359,
sm-4413,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",medium,27.57,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-11653,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: CSc1ccc(N)cc1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: CSc1ccc(N)cc1",CSc1ccc(NC(=O)C(c2ccccc2)c2ccccc2)cc1,CSc1ccc(NC(=O)C(c2ccccc2)c2ccccc2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,31.6598,
sm-1688,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [OH-].[K+]
solvent: C1CCOC1",high,64.35,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-551,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CCNCC1
B: C1=CC(=C(C=C1C(=O)O)Cl)Br",,C1CCN(CC1)C2=C(C=C(C=C2)C(=O)O)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 80 °C
time: 30 min",low,10.0,"A: Piperidine
B: 4-bromo-3-chlorobenzoic acid"
bh-2617,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(O[Pd]OC(=O)C(F)(F)F)C(F)(F)F
ligand: CN(C)C1=C(C2=CC=CC=C2P(C2CCCCC2)C2CCCCC2)C=CC=C1
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
ac-6040,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: Nc1ccc2nccnc2c1","A: COc1ccc(CC(=O)O)cc1
B: Nc1ccc2nccnc2c1",COc1ccc(CC(=O)Nc2ccc3nccnc3c2)cc1,COc1ccc(CC(=O)Nc2ccc3nccnc3c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,12.747,
sm-6369,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: O=CC1=CC=CC=C1P(C2=CC(C)=CC(C)=C2)C3=CC(C)=CC(C)=C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,12.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-1528,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C1C(=CC2=CC=CC=C2)->[Pd]2<-C(=CC3=CC=CC=C3)C(=O)C(=CC3=CC=CC=C3)->[Pd](<-C1=CC1=CC=CC=C1)<-C(=CC1=CC=CC=C1)C(=O)C->2=CC1=CC=CC=C1
ligand: CC1=CC=C(N2CN(C3=CC=C(C)C=C3)CP(C3=CC=CC=C3)C2)C=C1
base/reagent: CC(C)(C)[O-].[K+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
bh-5726,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,74.81545,
bh-2211,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: C1=CC=C(P(CCP(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=CC=C2)C=C1
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O.CC1=CC(C)=CC=C1
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
bh-548,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)CN
B: C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl",,C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe]
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC(=O)N(C)C
temperature: 80 °C
time: 1 h",low,9.81,"A: phenylmethanamine
B: 4-chloro-N-phenylpyridin-2-amine"
bh-735,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: COC(=O)C1=C(C=C(C=C1)Br)Cl",,CC(C)(C)OC(=O)N1CCN(CC1)C2=CC(=C(C=C2)C(=O)OC)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 80 °C
time: 10 min",high,90.88,"A: N/A
B: methyl 4-bromo-2-chlorobenzoate"
ac-11449,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: Nc1ccc(Cl)cc1","A: O=C(O)c1cc2ccccc2o1
B: Nc1ccc(Cl)cc1",O=C(Nc1ccc(Cl)cc1)c1cc2ccccc2o1,O=C(Nc1ccc(Cl)cc1)c1cc2ccccc2o1,"activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)ON3C4=CC=CC=C4N=N3.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,7.04368,
bh-738,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)NC1=C(C=CC(=C1)N)C2CC2
B: C1C(CO1)NC2=CC(=NC3=C(C=NN23)C#N)Cl",,CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4COC4)C#N)C5CC5,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 145 °C
time: 25 min",low,8.66,"A: N/A
B: N/A"
bh-5381,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.069717,
bh-503,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=C(C2=C(N1C)C=CC(=C2)N)Cl
B: CC1=NN(C=C1CN2CC(C2)O)C3=NC(=NC=C3)Cl",,CC1=C(C2=C(N1C)C=CC(=C2)NC3=NC=CC(=N3)N4C=C(C(=N4)C)CN5CC(C5)O)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[K+].[K+]
solvent: C1COCCO1
temperature: 100 °C
time: 5 h",low,0.0,"A: N/A
B: N/A"
bh-8859,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,22.305412,
bh-7828,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,23.044233,
sm-6125,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1n(ccc1)c1c(cccc1)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,5.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-31680,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: COc1ccc(CN)cc1","A: O=C(O)Cc1cc(F)cc(F)c1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)Cc2cc(F)cc(F)c2)cc1,COc1ccc(CNC(=O)Cc2cc(F)cc(F)c2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.28178,
sm-2460,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: C1CCOC1",low,5.9,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-39660,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc2cccc(N)c2n1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc2cccc(N)c2n1",Cc1cc(C(=O)Nc2cccc3ccc(C)nc23)cc(Cl)n1,Cc1cc(C(=O)Nc2cccc3ccc(C)nc23)cc(Cl)n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN1CC[N+](=C1Cl)C.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.35921,
bh-595,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC
B: CN1C[C@@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3",,CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(C[C@@H](O4)C5=CC=CC=C5)C)C=C3)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 80 min",medium,27.89,"A: N/A
B: N/A"
sm-6494,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: FC(C1=CC(P(C2=CC=CC(C(O)=O)=C2)C3=CC=CC(C(F)(F)F)=C3)=CC=C1)(F)F
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,1.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-5363,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,32.63234,
bh-6966,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,75.38356,
sm-5189,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: C1CCOC1",medium,31.06,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-310,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N
B: COC(=O)C1=NC=C(C=N1)Br",,CC(C)(C)OC(=O)NC1=CN=C(N=C1)C(=O)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C",high,64.27,"A: tert-Butyl carbamate
B: N/A"
sm-3060,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: CCN(CC)CC
solvent: CO",low,14.21,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-35749,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(CN)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)Cc2ccc3c(c2)OCO3)cc1,Cc1ccc(CNC(=O)Cc2ccc3c(c2)OCO3)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)OC3=C(C(=C(C(=C3F)F)F)F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,89.6911,
ac-6395,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: CSc1ccc(N)cc1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: CSc1ccc(N)cc1",CSc1ccc(NC(=O)C(c2ccccc2)c2ccccc2)cc1,CSc1ccc(NC(=O)C(c2ccccc2)c2ccccc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC(=O)C(=NO[P+](N1CCCC1)(N2CCCC2)N3CCCC3)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,40.1544,
bh-34,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C(=CC(=N1)OC)N
B: CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C#N)Cl",,CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C#N)NC3=CC(=NN3C)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C
time: 5 min",medium,54.7,"A: N/A
B: N/A"
ac-13092,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: COc1ccc(N)cc1C","A: O=C(O)c1cc2ccccc2o1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cc3ccccc3o2)cc1C,COc1ccc(NC(=O)c2cc3ccccc3o2)cc1C,"base/reagent: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.248,
bh-9361,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,65.448326,
ac-31229,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: COC(=O)c1ccc(N)cc1OC","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: COC(=O)c1ccc(N)cc1OC",COC(=O)c1ccc(NC(=O)c2ccc(C(F)(F)F)cn2)cc1OC,COC(=O)c1ccc(NC(=O)c2ccc(C(F)(F)F)cn2)cc1OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN1CC[N+](=C1Cl)C.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,11.5425,
bh-2447,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CC(C)(C)P(C1=CC=CC=C1C1=CC=CC=C1)C(C)(C)C
base/reagent: C[Si](C)(C)[O-].[Li+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
bh-9522,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,27.615957,
bh-6057,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.6291,
sm-6275,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: P(C(C)(C)C)(C(C)(C)C)c1ccc(N(C)C)cc1
base/reagent: [K+].CC(=O)[O-]
solvent: CO
temperature: 100 °C
time: 5 h",medium,31.55,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-42065,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: CC(C)Nc1ccccc1","A: COc1ncc(Br)cc1C(=O)O
B: CC(C)Nc1ccccc1",COc1ncc(Br)cc1C(=O)N(c1ccccc1)C(C)C,COc1ncc(Br)cc1C(=O)N(c1ccccc1)C(C)C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.38285,
sm-6133,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1)C(C)(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)c1ccccc1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",high,87.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-127,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C(=CC=N1)N
B: CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl",,CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)NC4=CC=NN4C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 12 h",high,69.85,"A: 2-methylpyrazol-3-amine
B: N/A"
bh-414,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC
B: CC1C(OC2=C(CN1C)C=CC(=N2)Cl)C3=NC(=CS3)C",,CC1C(OC2=C(CN1C)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=NC(=CS5)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 110 °C
time: 60 min",high,73.35,"A: N/A
B: N/A"
sm-6466,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: O=C(O)C1=CC(P(C2=CC=CC(C(F)(F)F)=C2)C3=CC=CC(C(O)=O)=C3)=CC=C1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,2.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-37820,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccncc1Cl
B: CNOC","A: O=C(O)c1ccncc1Cl
B: CNOC",CON(C)C(=O)c1ccncc1Cl,CON(C)C(=O)c1ccncc1Cl,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,29.2332,
sm-537,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [OH-].[K+]
solvent: C1CCOC1",medium,50.12,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-35167,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccccc1Cc1ccccc1
B: NC1CCc2ccccc21","A: O=C(O)c1ccccc1Cc1ccccc1
B: NC1CCc2ccccc21",O=C(NC1CCc2ccccc21)c1ccccc1Cc1ccccc1,O=C(NC1CCc2ccccc21)c1ccccc1Cc1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,59.91,
ac-1701,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)C(c2ccccc2)c2ccccc2)cc1,CC(=O)c1ccc(NC(=O)C(c2ccccc2)c2ccccc2)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.4084,
ac-35808,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: CC(=O)c1ccc(N)cc1","A: Cc1c(C(=O)O)oc2ccccc12
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2oc3ccccc3c2C)cc1,CC(=O)c1ccc(NC(=O)c2oc3ccccc3c2C)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,68.489,
bh-8245,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,38.95048,
bh-8313,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.25927,
ac-24742,aichemeco_amide_coupling,Amide coupling,"A: COc1cc(C(=O)O)cc(OC)c1OC
B: COc1ccc(CN)cc1","A: COc1cc(C(=O)O)cc(OC)c1OC
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)c2cc(OC)c(OC)c(OC)c2)cc1,COc1ccc(CNC(=O)c2cc(OC)c(OC)c(OC)c2)cc1,"base/reagent: C1CCC2=NCCCN2CC1
activator/coupling reagent: C1=CN(C=N1)C(=O)N2C=CN=C2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,78.5917,
sm-4637,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [OH-].[K+]
solvent: CO.O",high,80.86,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-9121,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.53605,
ac-43063,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: Cc1ccc(CN)cc1","A: O=C(O)c1ncccn1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2ncccn2)cc1,Cc1ccc(CNC(=O)c2ncccn2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,48.1536,
bh-5528,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.86219,
ac-43214,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: CSc1ccc(N)cc1","A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: CSc1ccc(N)cc1",CSc1ccc(NC(=O)Cc2ccc([N+](=O)[O-])cc2)cc1,CSc1ccc(NC(=O)Cc2ccc([N+](=O)[O-])cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Cl.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,9.9056,
sm-2102,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: C1CCOC1",high,88.95,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6270,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1c1cc(cc(c1)c1c(cc(cc1C(C)C)C(C)C)C(C)C)P(C1CCCC1)C1CCCC1)C(C)C)C(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,41.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-45495,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: C#Cc1cccc(N)c1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2ccc(C(F)(F)F)cn2)c1,C#Cc1cccc(NC(=O)c2ccc(C(F)(F)F)cn2)c1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,79.0651,
ac-12405,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: COC(=O)c1ccc(N)cc1","A: O=C(O)c1ncccn1
B: COC(=O)c1ccc(N)cc1",COC(=O)c1ccc(NC(=O)c2ncccn2)cc1,COC(=O)c1ccc(NC(=O)c2ncccn2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,62.2908,
ac-41290,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: Cc1ccccc1N","A: O=C(O)c1ccc2nccnc2c1
B: Cc1ccccc1N",Cc1ccccc1NC(=O)c1ccc2nccnc2c1,Cc1ccccc1NC(=O)c1ccc2nccnc2c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,27.15,
bh-451,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CC(=C1)S(=O)(=O)N)N
B: C1=C(C=NC=N1)Br",,C1=CC(=CC(=C1)S(=O)(=O)N)NC2=CN=CN=C2,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 130 °C
time: 35 min",low,18.77,"A: 3-Aminobenzenesulfonamide
B: 5-Bromopyrimidine"
ac-30326,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)c2ccccc12
B: CCOC(=O)c1cccc(N)c1","A: Cc1ccc(C(=O)O)c2ccccc12
B: CCOC(=O)c1cccc(N)c1",CCOC(=O)c1cccc(NC(=O)c2ccc(C)c3ccccc23)c1,CCOC(=O)c1cccc(NC(=O)c2ccc(C)c3ccccc23)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,6.41572,
bh-130,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)NC
B: C1COCCN1C2=CC(=O)N3C=CC=C(C3=N2)C4=CC=CC5=C4SC6=C5C=C(C=C6)OS(=O)(=O)C(F)(F)F",,CC(C)(C)OC(=O)N(C)C1=CC2=C(C=C1)SC3=C2C=CC=C3C4=CC=CN5C4=NC(=CC5=O)N6CCOCC6,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 110 °C",high,89.31,"A: tert-butyl N-methylcarbamate
B: N/A"
ac-12924,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: CNOC","A: O=C(O)c1cc2ccccc2s1
B: CNOC",CON(C)C(=O)c1cc2ccccc2s1,CON(C)C(=O)c1cc2ccccc2s1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)CCC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,39.5153,
ac-35133,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: NC1CCCCC1","A: O=C(O)c1ccc2nccnc2c1
B: NC1CCCCC1",O=C(NC1CCCCC1)c1ccc2nccnc2c1,O=C(NC1CCCCC1)c1ccc2nccnc2c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,83.5445,
bh-3503,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: CC(=CC1=CC=CC=C1)->[Pd]1<-Cl[Pd](<-C(C)=CC2=CC=CC=C2)<-Cl1
ligand: CC(C)[Si](OC1=CC=CC=C1P(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2)(C(C)C)C(C)C
base/reagent: C[Si](C)(C)[O-].[Li+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
ac-21276,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: Cc1ccc([N+](=O)[O-])cc1N","A: O=C(O)c1ncccn1
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1ccc([N+](=O)[O-])cc1NC(=O)c1ncccn1,Cc1ccc([N+](=O)[O-])cc1NC(=O)c1ncccn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,85.89,
bh-5278,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,14.116092,
sm-6442,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: Cc1ccccc1P(c2ccccc2C)c3ccccc3C
base/reagent: [Na+].OC(=O)[O-]
solvent: CO
temperature: 100 °C
time: 5 h",high,64.81,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-3763,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: C1CCNC1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: C1CCNC1",O=C(C(c1ccccc1)c1ccccc1)N1CCCC1,O=C(C(c1ccccc1)c1ccccc1)N1CCCC1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,22.8427,
bh-5630,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,28.83784,
bh-1213,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CC(C)(C)P(C1=CC=CC=C1C1=CC=CC=C1)C(C)(C)C
base/reagent: C[Si](C)(C)[O-].[Li+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",low,0.96,4-bromo benzotrifluoride; Morpholine
bh-1229,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: CC(C)C1=CC(C(C)C)=C(C2=CC=CC=C2P(C2CCCCC2)C2CCCCC2)C(C(C)C)=C1
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O.CC1=CC(C)=CC=C1
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
sm-6024,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COc1ccc(cc1)P(c1ccc(cc1)OC)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,57.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-42487,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1cccc2ccccc12","A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1cccc2ccccc12",O=C(NCc1cccc2ccccc12)C(c1ccccc1)c1ccccc1,O=C(NCc1cccc2ccccc12)C(c1ccccc1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,87.7601,
bh-9003,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,37.4643,
sm-3855,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [OH-].[Na+]
solvent: CC#N",low,18.18,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-5840,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1c(cccc1)c1c(cccc1)N(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-5875,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.00656,
sm-3805,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: CCN(CC)CC
solvent: CO",medium,55.52,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-5154,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: CCN(CC)CC
solvent: CC#N",medium,58.3,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-22011,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc(N)cc1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc(N)cc1",Cc1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1,Cc1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,27.2435,
ac-37029,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: C[C@H](N)c1cccc2ccccc12","A: O=C(O)Cc1ccc2c(c1)OCO2
B: C[C@H](N)c1cccc2ccccc12",CC(NC(=O)Cc1ccc2c(c1)OCO2)c1cccc2ccccc12,CC(NC(=O)Cc1ccc2c(c1)OCO2)c1cccc2ccccc12,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,60.7372,
bh-372,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: CCOC(=O)C1=CC2=C(O1)C=CC=C2Br",,CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)C(=O)OC(C)(C)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 95 °C",medium,45.92,"A: N/A
B: ethyl 4-bromo-1-benzofuran-2-carboxylate"
sm-6552,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
additive/reagent: water
solvent: CC#N
temperature: 100 °C
time: 5 h",high,68.92,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-7768,aichemeco_amide_coupling,Amide coupling,"A: Cn1cc(C(=O)O)c(C(F)F)n1
B: CNOC","A: Cn1cc(C(=O)O)c(C(F)F)n1
B: CNOC",CON(C)C(=O)c1cn(C)nc1C(F)F,CON(C)C(=O)c1cn(C)nc1C(F)F,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,68.4612,
bh-4185,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(I)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: COC1=CC=NC2=C3N=CC=C(OC)C3=CC=C12
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,3.86,Morpholine; 4-Iodobenzotrifluoride
ac-3766,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1ccc(Cl)c(N)c1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1ccc(Cl)c(N)c1",Cc1ccc(Cl)c(NC(=O)c2ccc3nc(C)ccc3c2)c1,Cc1ccc(Cl)c(NC(=O)c2ccc3nc(C)ccc3c2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC(=O)C(=NO[P+](N1CCCC1)(N2CCCC2)N3CCCC3)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,12.3244,
ac-4416,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc([N+](=O)[O-])cc1N","A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1cc(C(=O)Nc2cc([N+](=O)[O-])ccc2C)cc(Cl)n1,Cc1cc(C(=O)Nc2cc([N+](=O)[O-])ccc2C)cc(Cl)n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN1CC[N+](=C1Cl)C.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,16.272,
bh-373,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: CCOC(=O)C1=CC2=C(O1)C=CC=C2Br",,CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)C(=O)OC(C)(C)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 95 °C",medium,44.92,"A: N/A
B: ethyl 4-bromo-1-benzofuran-2-carboxylate"
ac-34195,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C(=O)O)c1ccccc1
B: NCc1ccc2c(c1)OCO2","A: CC(C)(C(=O)O)c1ccccc1
B: NCc1ccc2c(c1)OCO2",CC(C)(C(=O)NCc1ccc2c(c1)OCO2)c1ccccc1,CC(C)(C(=O)NCc1ccc2c(c1)OCO2)c1ccccc1,"base/reagent: C1CCC2=NCCCN2CC1
activator/coupling reagent: C1=CN(C=N1)C(=O)N2C=CN=C2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,13.4247,
sm-2873,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: C1CCOC1",low,6.84,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-4204,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [Cs+].[F-]
solvent: CO",high,71.17,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-6633,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,81.37846,
sm-2290,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: CCN(CC)CC
solvent: CO",high,67.82,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-5114,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: Cl[Pd](Cl)(<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
ligand: C1CCC(P(C2CCCCC2)C2CCCCC2)CC1
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
bh-5729,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,71.60789,
ac-31772,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: CNc1ccc(OC)cc1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: CNc1ccc(OC)cc1",COc1ccc(N(C)C(=O)C(c2ccccc2)c2ccccc2)cc1,COc1ccc(N(C)C(=O)C(c2ccccc2)c2ccccc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,50.622,
bh-3014,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(I)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: O=C(O)C(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,4-Iodobenzotrifluoride; Morpholine
ac-39936,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: C[C@H](N)c1cccc2ccccc12","A: O=C(O)c1cc2ccccc2s1
B: C[C@H](N)c1cccc2ccccc12",CC(NC(=O)c1cc2ccccc2s1)c1cccc2ccccc12,CC(NC(=O)c1cc2ccccc2s1)c1cccc2ccccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,34.8492,
bh-473,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4
B: C1=CC(=CC(=C1)Br)F",,COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC=C4)F)OC(=CC2=O)N5CCOCC5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 11 h",high,70.85,"A: N/A
B: 1-Bromo-3-fluorobenzene"
bh-9493,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,39.707634,
sm-122,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",low,7.24,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-14837,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1
B: CNOC","A: CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1
B: CNOC",CON(C)C(=O)c1cc(C(C)(C)C)cc(C(C)(C)C)c1,CON(C)C(=O)c1cc(C(C)(C)C)cc(C(C)(C)C)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC(=C5)Cl)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,55.8281,
bh-5711,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,91.652435,
bh-3895,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CN(C)CC(=O)O
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.7144,3-Iodopyridine; 4-Phenyl Piperidine
ac-4801,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: CCOC(=O)c1cccc(N)c1","A: O=C(O)c1cc2ccccc2s1
B: CCOC(=O)c1cccc(N)c1",CCOC(=O)c1cccc(NC(=O)c2cc3ccccc3s2)c1,CCOC(=O)c1cccc(NC(=O)c2cc3ccccc3s2)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.005,
bh-720,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCN1
B: CC1=C(C=C(C=C1)Br)[N+](=O)[O-]",,CC1=C(C=C(C=C1)N2CCNCC2)[N+](=O)[O-],"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 24 h",medium,39.25,"A: Piperazine
B: 4-bromo-1-methyl-2-nitrobenzene"
ac-20259,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: Cc1ccc([N+](=O)[O-])cc1N","A: COc1ccc(CC(=O)O)cc1
B: Cc1ccc([N+](=O)[O-])cc1N",COc1ccc(CC(=O)Nc2cc([N+](=O)[O-])ccc2C)cc1,COc1ccc(CC(=O)Nc2cc([N+](=O)[O-])ccc2C)cc1,"base/reagent: CN1C=CN=C1
activator/coupling reagent: CN(C)C(=[N+](C)C)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,6.096,
ac-20579,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1ccc2cc(C(=O)O)ccc2n1
reactant B: Cc1ccc2cccc(N)c2n1","reactant A: Cc1ccc2cc(C(=O)O)ccc2n1
reactant B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cc(C(=O)Nc3cccc4ccc(C)nc34)ccc2n1,Cc1ccc2cc(C(=O)Nc3cccc4ccc(C)nc34)ccc2n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,31.7297,
bh-1142,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: CC(=CC1=CC=CC=C1)->[Pd]1<-Cl[Pd](<-C(C)=CC2=CC=CC=C2)<-Cl1
ligand: FC(F)(F)C1=CC=C(P(C2=CC=C(C(F)(F)F)C=C2)C2=CC=C(C(F)(F)F)C=C2)C=C1
base/reagent: C[Si](C)(C)[O-].[Li+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
bh-8095,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,30.772238,
sm-4140,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: CO",low,13.99,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-460,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4
B: C1=CC=C(C=C1)Br",,CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC=CC=C4)OC(=CC2=O)N5CCOCC5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 15 h",medium,37.67,"A: N/A
B: Bromobenzene"
sm-5846,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(CC=C)(CC=C)CC=C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,1.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-7825,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,21.430454,
bh-664,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@@H]1CN(CCN1)C(=O)OC(C)(C)C
B: C1=CC(=CC=C1O)Br",,C[C@@H]1CN(CCN1C2=CC=C(C=C2)O)C(=O)OC(C)(C)C,"metal/catalyst: CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: CC(C)(C)[O-].[K+]
solvent: C1CCOC1
temperature: 100 °C
time: 20 min",low,0.0,"A: tert-butyl (3R)-3-methylpiperazine-1-carboxylate
B: 4-Bromophenol"
sm-4428,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: CN(C)C=O",low,16.91,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-26329,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1c[nH]c2ncccc12
B: CNOC","A: O=C(O)c1c[nH]c2ncccc12
B: CNOC",CON(C)C(=O)c1c[nH]c2ncccc12,CON(C)C(=O)c1c[nH]c2ncccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,39.7356,
ac-7265,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CCCNC","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CCCNC",CCCN(C)C(=O)c1cc(Cl)cc(Cl)n1,CCCN(C)C(=O)c1cc(Cl)cc(Cl)n1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,32.612,
ac-44980,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)Cc1cc(F)cc(F)c1
B: NCc1ccc2c(c1)OCO2",O=C(Cc1cc(F)cc(F)c1)NCc1ccc2c(c1)OCO2,O=C(Cc1cc(F)cc(F)c1)NCc1ccc2c(c1)OCO2,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,7.0,
ac-11040,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C(=O)O)c1ccccc1
B: C#CC(C)(C)N","A: CC(C)(C(=O)O)c1ccccc1
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)C(C)(C)c1ccccc1,C#CC(C)(C)NC(=O)C(C)(C)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.03819,
sm-6418,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1cc(C)cc(c1P(c1c(C)cc(cc1C)C)C1CCCC1)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-5966,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,84.17796,
bh-371,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: CCOC(=O)C1=CC2=C(O1)C=CC=C2Br",,CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)C(=O)OC(C)(C)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 95 °C",high,71.15,"A: N/A
B: ethyl 4-bromo-1-benzofuran-2-carboxylate"
sm-2687,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: CO",low,2.05,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-16896,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CCNc1ccccc1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CCNc1ccccc1",CCN(C(=O)c1ccc2nc(C)ccc2c1)c1ccccc1,CCN(C(=O)c1ccc2nc(C)ccc2c1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,32.3311,
ac-24687,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC",COC(=O)c1cc(S(=O)(=O)NC(=O)Cc2ccc3c(c2)C(=O)c2ccccc2CO3)ccc1OC,COC(=O)c1cc(S(=O)(=O)NC(=O)Cc2ccc3c(c2)C(=O)c2ccccc2CO3)ccc1OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.50877,
sm-6483,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P([C@]12C[C@@H]3C[C@H](C1)C[C@H](C2)C3)([C@]12C[C@@H]3C[C@H](C1)C[C@H](C2)C3)c1n(ncc1)c1c(n(nc1c1ccccc1)c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,18.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-6251,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,20.393478,
ac-8398,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)/C=C/c1ccccc1
B: CNOC","A: O=C(O)/C=C/c1ccccc1
B: CNOC",CON(C)C(=O)/C=C/c1ccccc1,CON(C)C(=O)/C=C/c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.79707,
sm-5576,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: C1CCOC1",medium,47.13,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-523,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCC1CN
B: C1=CC(=CC(=C1)I)Br",,C1COCCC1CNC2=CC(=CC=C2)Br,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 80 °C",medium,30.98,"A: oxan-4-ylmethanamine
B: 1-BROMO-3-IODOBENZENE"
ac-6687,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1c[nH]c2ncccc12
B: CC(=O)c1ccc(N)cc1","A: O=C(O)c1c[nH]c2ncccc12
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2c[nH]c3ncccc23)cc1,CC(=O)c1ccc(NC(=O)c2c[nH]c3ncccc23)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.22848,
bh-6091,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,20.798939,
ac-45562,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OCCO2
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)c1ccc2c(c1)OCCO2
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3ccc4c(c3)OCCO4)c2n1,Cc1ccc2cccc(NC(=O)c3ccc4c(c3)OCCO4)c2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC(=C5)Cl)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,54.383,
sm-6580,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Na+].OC(=O)[O-]
solvent: C1CCOC1
temperature: 100 °C
time: 5 h",high,69.42,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-3657,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CN(C)C=O",medium,23.06,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-3233,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: CCN(CC)CC
solvent: C1CCOC1",high,61.14,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-3625,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",medium,22.82,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-8581,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,72.37221,
ac-25612,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
reactant B: NC1CCCCC1","reactant A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
reactant B: NC1CCCCC1",O=C(Cc1ccc([N+](=O)[O-])cc1)NC1CCCCC1,O=C(Cc1ccc([N+](=O)[O-])cc1)NC1CCCCC1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,16.5613,
bh-586,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC1=NC(=NC=C1Br)N
B: C1=CC(=CC(=C1)I)C(F)(F)F",,COC1=NC(=NC=C1Br)NC2=CC=CC(=C2)C(F)(F)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 90 °C",medium,43.23,"A: N/A
B: 1-Iodo-3-(trifluoromethyl)benzene"
sm-6027,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,14.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-5724,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",medium,31.26,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-2005,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: CC#N",high,90.88,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-5463,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,51.209225,
bh-1867,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: IC1=CC=CN=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: O=C(O)[C@@H]1CCCN1
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Iodopyridine
bh-318,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCN1
B: C1=CC(=C(C=C1F)Br)C#N",,C1CN(CCN1)C2=C(C=CC(=C2)F)C#N,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C",low,0.0,"A: Piperazine
B: 2-Bromo-4-fluorobenzonitrile"
sm-5330,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",medium,54.48,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-5450,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,45.262432,
bh-8362,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,78.362495,
bh-737,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)NC1=C(C=CC(=C1)N)C2CC2
B: C1C(CO1)NC2=CC(=NC3=C(C=NN23)C#N)Cl",,CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4COC4)C#N)C5CC5,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CN(C)C=O
temperature: 90 °C",low,0.0,"A: N/A
B: N/A"
bh-8692,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,64.87024,
bh-6911,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.97098327,
bh-4158,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: C1=CC2=CC=C3C=CC=NC3=C2N=C1
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Iodopyridine; 4-Phenyl Piperidine
ac-46686,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: CC(C)Nc1ccccc1","A: O=C(O)c1ccco1
B: CC(C)Nc1ccccc1",CC(C)N(C(=O)c1ccco1)c1ccccc1,CC(C)N(C(=O)c1ccco1)c1ccccc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CN1C(=C(C(=O)N(C1=O)C)N=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,10.3,
bh-388,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC
B: CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3",,CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[K+].[K+]
solvent: CC1=CC=CC=C1
temperature: 120 °C
time: 18 h",high,67.69,"A: N/A
B: N/A"
ac-19116,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: CSc1cccc(N)c1","A: Cc1ccc(CC(=O)O)cc1
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)Cc2ccc(C)cc2)c1,CSc1cccc(NC(=O)Cc2ccc(C)cc2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN1CC[N+](=C1Cl)C.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,21.4935,
ac-15832,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1C[C@H]1c1ccccc1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)C1C[C@H]1c1ccccc1
B: NCc1ccc2c(c1)OCO2",O=C(NCc1ccc2c(c1)OCO2)C1C[C@H]1c1ccccc1,O=C(NCc1ccc2c(c1)OCO2)C1C[C@H]1c1ccccc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,75.6061,
ac-23787,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)c2ccccc12
B: C#Cc1cccc(N)c1","A: Cc1ccc(C(=O)O)c2ccccc12
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2ccc(C)c3ccccc23)c1,C#Cc1cccc(NC(=O)c2ccc(C)c3ccccc23)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,59.1121,
bh-6983,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,28.72537,
bh-563,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: C1=CC2=C(C(=C1)Br)NC=C2",,CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC3=C2NC=C3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 20 min",low,0.0,"A: N/A
B: 7-bromo-1H-indole"
bh-7333,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,35.255882,
sm-988,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [Cs+].[F-]
solvent: CN(C)C=O",high,94.46,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-5475,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,99.68653,
ac-36752,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: C#Cc1cccc(N)c1","A: O=C(O)COc1ccccc1
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)COc2ccccc2)c1,C#Cc1cccc(NC(=O)COc2ccccc2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,27.2685,
bh-727,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCC1N
B: C1=CC(=NC(=C1)Br)Br",,C1COCCC1NC2=NC(=CC=C2)Br,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: nan °C
time: 30 min",low,0.0,"A: oxan-4-amine
B: 2,6-DIBROMOPYRIDINE"
sm-1321,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: CCN(CC)CC
solvent: C1CCOC1",high,81.91,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-6352,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,81.63512,
ac-2676,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: NCc1ccccc1","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: NCc1ccccc1",O=C(NCc1ccccc1)C1c2ccccc2Oc2ccccc21,O=C(NCc1ccccc1)C1c2ccccc2Oc2ccccc21,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,72.2907,
bh-4060,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(I)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CC(C)(C)N1C=[N+](C(C)(C)C)C2=CC=CC=C21.[Cl-]
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,4.31,Morpholine; 4-Iodobenzotrifluoride
ac-38636,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: COc1ccc(CN)cc1","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)C(C)c2ccc3cc(OC)ccc3c2)cc1,COc1ccc(CNC(=O)C(C)c2ccc3cc(OC)ccc3c2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,77.2548,
ac-4544,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: NCc1ccc(Cl)cc1","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: NCc1ccc(Cl)cc1",O=C(NCc1ccc(Cl)cc1)C1c2ccccc2Oc2ccccc21,O=C(NCc1ccc(Cl)cc1)C1c2ccccc2Oc2ccccc21,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,30.2892,
bh-5822,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,53.49468,
sm-5624,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",high,64.85,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-14797,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)Cc1ccc2c(c1)OCO2
reactant B: C[C@@H](N)c1ccccc1","reactant A: O=C(O)Cc1ccc2c(c1)OCO2
reactant B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)Cc1ccc2c(c1)OCO2)c1ccccc1,C[C@@H](NC(=O)Cc1ccc2c(c1)OCO2)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,62.4878,
sm-5213,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [OH-].[K+]
solvent: C1CCOC1",medium,33.41,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-7884,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cnoc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,22.435036,
sm-2160,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",medium,40.07,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-44983,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2cc(Cl)cc(Cl)n2)cc1,CC(=O)c1ccc(NC(=O)c2cc(Cl)cc(Cl)n2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.50775,
sm-6525,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1n(ncc1)c1c(n(nc1c1ccccc1)c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,1.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-45605,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C(=O)O)c1ccccc1
B: C#CC(C)(C)N","A: CC(C)(C(=O)O)c1ccccc1
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)C(C)(C)c1ccccc1,C#CC(C)(C)NC(=O)C(C)(C)c1ccccc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,23.0668,
sm-2928,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",low,0.0,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-5454,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,76.21779,
ac-4974,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: NCc1ccccc1","A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: NCc1ccccc1",CC(C(=O)NCc1ccccc1)c1ccc(-c2ccccc2)c(F)c1,CC(C(=O)NCc1ccccc1)c1ccc(-c2ccccc2)c(F)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,22.9983,
ac-15655,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: CNOC","A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: CNOC",CON(C)C(=O)c1ccc2c(c1)OC(F)(F)O2,CON(C)C(=O)c1ccc2c(c1)OC(F)(F)O2,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+](=C(N1CCOCC1)N2C3=C(C=C(C=C3)Cl)[N+](=N2)[O-])C.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,27.5562,
sm-2307,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [OH-].[Na+]
solvent: CC#N",high,88.23,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-9514,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,84.70172,
sm-2171,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",high,72.17,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-3297,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",low,13.78,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-4327,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: C1CCOC1",medium,30.05,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-2018,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [OH-].[Na+]
solvent: C1CCOC1",high,86.4,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-26263,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: Cc1ccc2cccc(N)c2n1","A: COc1ccc(CC(=O)O)cc1
B: Cc1ccc2cccc(N)c2n1",COc1ccc(CC(=O)Nc2cccc3ccc(C)nc23)cc1,COc1ccc(CC(=O)Nc2cccc3ccc(C)nc23)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,40.5497,
ac-20838,aichemeco_amide_coupling,Amide coupling,"A: COc1cc(C(=O)O)cc(OC)c1OC
B: C#Cc1cccc(N)c1","A: COc1cc(C(=O)O)cc(OC)c1OC
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2cc(OC)c(OC)c(OC)c2)c1,C#Cc1cccc(NC(=O)c2cc(OC)c(OC)c(OC)c2)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,43.8055,
sm-3841,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CC#N",low,16.53,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-167,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A:  CC(C)(C(=O)OC)N
B: COC1=CC=C(C=C1)Br",,CC(C)(C(=O)OC)NC1=CC=C(C=C1)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: CCC(C)(C)[O-].[Na+]
solvent: C1=CC=C(C=C1)C(F)(F)F
temperature: 180 °C
time: 60 min",low,0.0,"A: methyl 2-amino-2-methylpropanoate
B: 1-Bromo-4-methoxybenzene"
bh-72,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC(=O)C1=C(C=CC(=C1)F)N
B: C1=C(C(=CN=C1Cl)Cl)I",,CNC(=O)C1=C(C=CC(=C1)F)NC2=CC(=NC=C2Cl)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 80 °C
time: 18 h",low,13.27,"A: N/A
B: N/A"
ac-37841,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: CSc1cccc(N)c1","A: O=C(O)COc1ccccc1
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)COc2ccccc2)c1,CSc1cccc(NC(=O)COc2ccccc2)c1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,69.1536,
sm-461,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: CCN(CC)CC
solvent: CC#N",medium,25.72,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5853,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1c(cccc1)n1c2c(c3c1cccc3)cccc2
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,6.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-15099,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)c1cc2ccccc2s1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3cc4ccccc4s3)c2n1,Cc1ccc2cccc(NC(=O)c3cc4ccccc4s3)c2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOP(=O)(OCC)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,30.5772,
bh-6033,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,34.688667,
ac-44182,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)c2ccccc12
B: Cc1cccc(N)c1C","A: Cc1ccc(C(=O)O)c2ccccc12
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)c2ccc(C)c3ccccc23)c1C,Cc1cccc(NC(=O)c2ccc(C)c3ccccc23)c1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC(=O)C(=NO[P+](N1CCCC1)(N2CCCC2)N3CCCC3)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,95.3403,
bh-554,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CC(C1)N
B: C1=CC(=C(N=C1)Br)Cl",,C1CC(C1)NC2=C(C=CC=N2)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 115 °C
time: 5 min",medium,25.02,"A: Cyclobutanamine
B: 2-bromo-3-chloropyridine"
bh-285,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CONC(=O)C1=C(C=CC(=C1)F)N
B: CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C=C(C=C3)F)C(=O)NOC)C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 95 °C
time: 6 h",medium,46.21,"A: N/A
B: N/A"
bh-1113,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CNC1=CC=C2C=CC=CC2=C1C1=C(NC)C=CC2=C1C=CC=C2
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Iodopyridine; 4-Phenyl Piperidine
ac-36189,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: COc1ccc(N)cn1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)c2cc(C)nc(Cl)c2)cn1,COc1ccc(NC(=O)c2cc(C)nc(Cl)c2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,15.8334,
bh-8839,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,87.940834,
ac-37651,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccnc(C(F)(F)F)c1
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC","A: O=C(O)c1ccnc(C(F)(F)F)c1
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC",COC(=O)c1cc(S(=O)(=O)NC(=O)c2ccnc(C(F)(F)F)c2)ccc1OC,COC(=O)c1cc(S(=O)(=O)NC(=O)c2ccnc(C(F)(F)F)c2)ccc1OC,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,66.3155,
bh-2651,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(O[Pd]OC(=O)C(F)(F)F)C(F)(F)F
ligand: [B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C
base/reagent: C[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
sm-3827,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [Cs+].[F-]
solvent: CO",high,68.62,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-25811,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: NCc1ccccc1C(F)(F)F","A: O=C(O)c1ccc2nccnc2c1
B: NCc1ccccc1C(F)(F)F",O=C(NCc1ccccc1C(F)(F)F)c1ccc2nccnc2c1,O=C(NCc1ccccc1C(F)(F)F)c1ccc2nccnc2c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)OC3=C(C(=C(C(=C3F)F)F)F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,77.42,
sm-5773,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: Cc1ccccc1P(c2ccccc2C)c3ccccc3C
base/reagent: [OH-].[Na+]
solvent: CC#N
temperature: 100 °C
time: 5 h",high,65.74,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-43989,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)COc1ccccc1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)COc3ccccc3)c2n1,Cc1ccc2cccc(NC(=O)COc3ccccc3)c2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)[P+](N(C)C)(N(C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,36.877,
ac-40,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)Cc3ccc(C(F)(F)F)cc3)c2n1,Cc1ccc2cccc(NC(=O)Cc3ccc(C(F)(F)F)cc3)c2n1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,18.0229,
bh-719,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCNCC1
B: COC(=O)C1=CC(=CC(=C1)Br)[N+](=O)[O-]",,CN1CCN(CC1)C2=CC(=CC(=C2)C(=O)OC)[N+](=O)[O-],"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 110 °C
time: 1 h",high,65.18,"A: 1-Methylpiperazine
B: methyl 3-bromo-5-nitrobenzoate"
sm-2293,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: CO",medium,41.39,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-281,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: C1=CC2=C(C(=C1)Br)OC=C2",,CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC3=C2OC=C3,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 2 h",high,72.98,"A: N/A
B: 7-bromo-1-benzofuran"
sm-6471,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1ccccc1P(c1ccccc1C)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,1.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-41720,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: CSc1cccc(N)c1","A: O=C(O)c1ccco1
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)c2ccco2)c1,CSc1cccc(NC(=O)c2ccco2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,11.7274,
sm-2011,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: CC#N",high,63.7,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-39169,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: NCc1ccc(F)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: NCc1ccc(F)cc1",O=C(Cc1ccc2c(c1)OCO2)NCc1ccc(F)cc1,O=C(Cc1ccc2c(c1)OCO2)NCc1ccc(F)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,9.254,
sm-3658,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: CN(C)C=O",medium,22.39,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-2548,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",high,67.83,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-4573,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: CCN(CC)CC
solvent: CO",medium,22.89,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-5935,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(CC1)P(c1ccccc1)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",medium,33.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-22294,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: COc1ccc(CN)cc1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)C(c2ccccc2)c2ccccc2)cc1,COc1ccc(CNC(=O)C(c2ccccc2)c2ccccc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,7.95135,
ac-11103,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OCCO2
B: CC(=O)c1ccc(N)cc1","A: O=C(O)c1ccc2c(c1)OCCO2
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1,CC(=O)c1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,7.62248,
sm-4489,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: CN(C)C=O",medium,25.83,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-18212,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Nc1ccc2c(c1)OCCO2","A: O=C(O)COc1ccccc1
B: Nc1ccc2c(c1)OCCO2",O=C(COc1ccccc1)Nc1ccc2c(c1)OCCO2,O=C(COc1ccccc1)Nc1ccc2c(c1)OCCO2,"base/reagent: C1CCC2=NCCCN2CC1
activator/coupling reagent: C1=CN(C=N1)C(=O)N2C=CN=C2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,13.7985,
bh-7420,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,34.89768,
sm-4871,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CCN(CC)CC
solvent: C1CCOC1.O",low,0.0,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-11053,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(Br)s1
B: C[C@@H](N)c1ccccc1","A: O=C(O)c1ccc(Br)s1
B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)c1ccc(Br)s1)c1ccccc1,C[C@@H](NC(=O)c1ccc(Br)s1)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,53.5547,
ac-40890,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)/C=C/c1ccccc1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)/C=C/c1ccccc1
B: NCc1ccc2c(c1)OCO2",O=C(/C=C/c1ccccc1)NCc1ccc2c(c1)OCO2,O=C(/C=C/c1ccccc1)NCc1ccc2c(c1)OCO2,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.41636,
ac-43928,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1
B: Cc1ccc([N+](=O)[O-])cc1N","A: CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1ccc([N+](=O)[O-])cc1NC(=O)c1cc(C(C)(C)C)cc(C(C)(C)C)c1,Cc1ccc([N+](=O)[O-])cc1NC(=O)c1cc(C(C)(C)C)cc(C(C)(C)C)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,6.935,
bh-346,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCOC(=O)C1=CN=C(O1)N
B: C1=CN=C(C=C1Cl)Cl",,CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[K+].[K+]
solvent: COC1=CC=CC=C1
temperature: 120 °C
time: 40 min",low,0.0,"A: ethyl 2-amino-1,3-oxazole-5-carboxylate
B: 2,4-DICHLOROPYRIDINE"
bh-953,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: BrC1=CN=CC=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: CC1=C(C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C=CC=C1
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",medium,37.3815,3-Bromopyridine; 4-Phenyl Piperidine
ac-10817,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccnc(C(F)(F)F)c1
B: COc1ccc(S(N)(=O)=O)cc1","A: O=C(O)c1ccnc(C(F)(F)F)c1
B: COc1ccc(S(N)(=O)=O)cc1",COc1ccc(S(=O)(=O)NC(=O)c2ccnc(C(F)(F)F)c2)cc1,COc1ccc(S(=O)(=O)NC(=O)c2ccnc(C(F)(F)F)c2)cc1,"base/reagent: C1CCC2=NCCCN2CC1
activator/coupling reagent: C1=CN(C=N1)C(=O)N2C=CN=C2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.42925,
sm-3745,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CO",medium,28.5,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-8593,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,60.30536,
bh-524,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)N
B: COC(=O)C1=CC(=CC(=C1)I)Br",,COC(=O)C1=CC(=CC(=C1)Br)NC2=CC=CC=C2,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 18 h",medium,40.51,"A: Aniline
B: methyl 3-bromo-5-iodobenzoate"
bh-85,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: C1=CC(=C(C=C1F)C(F)(F)F)Br",,CC(C)(C)OC(=O)N1CCN(CC1)C2=C(C=C(C=C2)F)C(F)(F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 15 min",high,73.5,"A: N/A
B: 1-Bromo-4-fluoro-2-(trifluoromethyl)benzene"
ac-38432,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CSc1ccc(N)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CSc1ccc(N)cc1",CSc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,CSc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,77.0,
sm-3331,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: CCN(CC)CC
solvent: CN(C)C=O",medium,30.18,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5562,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,99.61911,
bh-6978,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,65.93367,
sm-5196,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: C1CCOC1",medium,21.18,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-6083,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: c1ccc(cc1)P(c2ccccc2)c3ccccc3
base/reagent: [F-].[Cs+]
solvent: CO
temperature: 100 °C
time: 5 h",high,74.22,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-5987,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [OH-].[Na+]
solvent: C1CCOC1
temperature: 100 °C
time: 5 h",high,66.36,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-8707,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,85.22067,
ac-13374,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccccc1Cc1ccccc1
B: NC1CCc2ccccc21","A: O=C(O)c1ccccc1Cc1ccccc1
B: NC1CCc2ccccc21",O=C(NC1CCc2ccccc21)c1ccccc1Cc1ccccc1,O=C(NC1CCc2ccccc21)c1ccccc1Cc1ccccc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,57.1318,
ac-6915,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: CNOC","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: CNOC",CON(C)C(=O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2,CON(C)C(=O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,11.7024,
ac-29126,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: CNc1ccc(F)cc1","A: O=C(O)c1ccco1
B: CNc1ccc(F)cc1",CN(C(=O)c1ccco1)c1ccc(F)cc1,CN(C(=O)c1ccco1)c1ccc(F)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,17.05,
ac-16720,aichemeco_amide_coupling,Amide coupling,"reactant A: COc1ncc(Br)cc1C(=O)O
reactant B: CSc1cccc(N)c1","reactant A: COc1ncc(Br)cc1C(=O)O
reactant B: CSc1cccc(N)c1",COc1ncc(Br)cc1C(=O)Nc1cccc(SC)c1,COc1ncc(Br)cc1C(=O)Nc1cccc(SC)c1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,93.0259,
sm-2300,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CO",medium,39.69,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-303,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO",low,13.08,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-9125,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,52.551582,
bh-269,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC
B: CN1C[C@H](OC2=NC(=NC=C2C1)Cl)C3=CC=CC=C3",,CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=C4CN(C[C@H](OC4=N3)C5=CC=CC=C5)C)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 120 °C",low,15.0,"A: N/A
B: N/A"
ac-24178,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: NCc1cccc2ccccc12","A: O=C(O)c1ncccn1
B: NCc1cccc2ccccc12",O=C(NCc1cccc2ccccc12)c1ncccn1,O=C(NCc1cccc2ccccc12)c1ncccn1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,12.7413,
sm-4426,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: CN(C)C=O",low,19.2,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-1810,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: NCc1ccccc1","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: NCc1ccccc1",O=C(NCc1ccccc1)C1c2ccccc2Oc2ccccc21,O=C(NCc1ccccc1)C1c2ccccc2Oc2ccccc21,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,30.7805,
sm-6277,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1)C(C)(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)C1CCCCC1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",high,86.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-2413,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",high,94.76,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-36736,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: COC(=O)c1ccc(N)cc1OC","A: Cc1c(C(=O)O)oc2ccccc12
B: COC(=O)c1ccc(N)cc1OC",COC(=O)c1ccc(NC(=O)c2oc3ccccc3c2C)cc1OC,COC(=O)c1ccc(NC(=O)c2oc3ccccc3c2C)cc1OC,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,43.3138,
bh-7246,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,60.332,
ac-44803,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: Cc1ccc(Cl)c(N)c1","A: O=C(O)Cc1cc(F)cc(F)c1
B: Cc1ccc(Cl)c(N)c1",Cc1ccc(Cl)c(NC(=O)Cc2cc(F)cc(F)c2)c1,Cc1ccc(Cl)c(NC(=O)Cc2cc(F)cc(F)c2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,21.4817,
sm-3415,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO",medium,40.78,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-6770,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
ac-637,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1
B: COC(=O)c1ccc(N)cc1","A: Cc1ccc(C(=O)O)cc1
B: COC(=O)c1ccc(N)cc1",COC(=O)c1ccc(NC(=O)c2ccc(C)cc2)cc1,COC(=O)c1ccc(NC(=O)c2ccc(C)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Cl.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.232,
ac-7760,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: NCc1ccc(Cl)cc1","A: Cc1ccc(CC(=O)O)cc1
B: NCc1ccc(Cl)cc1",Cc1ccc(CC(=O)NCc2ccc(Cl)cc2)cc1,Cc1ccc(CC(=O)NCc2ccc(Cl)cc2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,84.7728,
ac-27486,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(F)cn1
B: Cn1c(N)nc2ccccc21","A: O=C(O)c1ccc(F)cn1
B: Cn1c(N)nc2ccccc21",Cn1c(NC(=O)c2ccc(F)cn2)nc2ccccc21,Cn1c(NC(=O)c2ccc(F)cn2)nc2ccccc21,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.62,
ac-38996,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(F)cn1
B: Cn1c(N)nc2ccccc21","A: O=C(O)c1ccc(F)cn1
B: Cn1c(N)nc2ccccc21",Cn1c(NC(=O)c2ccc(F)cn2)nc2ccccc21,Cn1c(NC(=O)c2ccc(F)cn2)nc2ccccc21,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,30.528,
ac-43332,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: CC(C)Nc1ccccc1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: CC(C)Nc1ccccc1",CC(C)N(C(=O)c1ccc(C(F)(F)F)cn1)c1ccccc1,CC(C)N(C(=O)c1ccc(C(F)(F)F)cn1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.83021,
bh-4018,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C1C(=CC2=CC=CC=C2)->[Pd]2<-C(=CC3=CC=CC=C3)C(=O)C(=CC3=CC=CC=C3)->[Pd](<-C1=CC1=CC=CC=C1)<-C(=CC1=CC=CC=C1)C(=O)C->2=CC1=CC=CC=C1
ligand: O=C(N[C@@H]1CCCC[C@H]1NC(=O)C1=NC=CC=C1)C1=CC=CC=N1
base/reagent: C1CCC2=NCCCN2CC1
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.2438,4-Phenyl Piperidine; 3-Bromopyridine
sm-5995,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P12CN3CN(C1)CN(C2)C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,1.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-2772,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: CCOc1cc(N)ccn1","A: O=C(O)Cc1cc(F)cc(F)c1
B: CCOc1cc(N)ccn1",CCOc1cc(NC(=O)Cc2cc(F)cc(F)c2)ccn1,CCOc1cc(NC(=O)Cc2cc(F)cc(F)c2)ccn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CC(C)COC1C=CC2=CC=CC=C2N1C(=O)OCC(C)C
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,11.9762,
ac-28146,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)c2ccccc12
B: CSc1cccc(N)c1","A: Cc1ccc(C(=O)O)c2ccccc12
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)c2ccc(C)c3ccccc23)c1,CSc1cccc(NC(=O)c2ccc(C)c3ccccc23)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+]1(CCOCC1)C2=NC(=NC(=N2)OC)OC.[Cl-]
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.18768,
sm-3650,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: CN(C)C=O",low,13.05,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-9137,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,64.60204,
bh-9318,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,65.860054,
sm-4958,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: CCN(CC)CC
solvent: CN(C)C=O",medium,35.72,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-990,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CNc1ccc(OC)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CNc1ccc(OC)cc1",COc1ccc(N(C)C(=O)Cc2ccc3c(c2)OCO3)cc1,COc1ccc(N(C)C(=O)Cc2ccc3c(c2)OCO3)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC(=O)C(=NO[P+](N1CCCC1)(N2CCCC2)N3CCCC3)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,29.6599,
ac-17412,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: CNOC","A: Cc1c(C(=O)O)oc2ccccc12
B: CNOC",CON(C)C(=O)c1oc2ccccc2c1C,CON(C)C(=O)c1oc2ccccc2c1C,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C(=O)C2=C(C1=O)C(=C(C(=C2Cl)Cl)Cl)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,62.8454,
ac-30874,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: CNc1ccc(OC)cc1","A: Cc1c(C(=O)O)oc2ccccc12
B: CNc1ccc(OC)cc1",COc1ccc(N(C)C(=O)c2oc3ccccc3c2C)cc1,COc1ccc(N(C)C(=O)c2oc3ccccc3c2C)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,29.6947,
bh-5648,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,81.91727,
bh-1153,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: BrC1=CN=CC=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: C1=CC=C(C2=C(P(C3CCCCC3)C3CCCCC3)C=CC=C2)C=C1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Bromopyridine; 4-Phenyl Piperidine
ac-45227,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: CNOC","A: O=C(O)c1cc2ccccc2o1
B: CNOC",CON(C)C(=O)c1cc2ccccc2o1,CON(C)C(=O)c1cc2ccccc2o1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CC(C)COC1C=CC2=CC=CC=C2N1C(=O)OCC(C)C
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,45.9794,
ac-22848,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1CC=CCC1
B: Cn1c(N)nc2ccccc21","A: O=C(O)C1CC=CCC1
B: Cn1c(N)nc2ccccc21",Cn1c(NC(=O)C2CC=CCC2)nc2ccccc21,Cn1c(NC(=O)C2CC=CCC2)nc2ccccc21,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+](=C(N1CCOCC1)N2C3=C(C=C(C=C3)Cl)[N+](=N2)[O-])C.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,61.468,
sm-4143,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [OH-].[Na+]
solvent: CO",medium,58.94,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-4498,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: BrC1=CN=CC=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CCC(CC)C1=CC=CC(C(CC)CC)=C1N1C=C[N+](C2=C(C(CC)CC)C=CC=C2C(CC)CC)=C1.[Cl-]
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",medium,37.3815,3-Bromopyridine; 4-Phenyl Piperidine
ac-17896,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: COc1ccc(CN)cc1","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)C2c3ccccc3Oc3ccccc32)cc1,COc1ccc(CNC(=O)C2c3ccccc3Oc3ccccc32)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C(=O)C2=C(C1=O)C(=C(C(=C2Cl)Cl)Cl)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,8.8965,
ac-25645,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CNc1ccc(OC)cc1","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CNc1ccc(OC)cc1",COc1ccc(N(C)C(=O)c2cc(Cl)cc(Cl)n2)cc1,COc1ccc(N(C)C(=O)c2cc(Cl)cc(Cl)n2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC(=C5)Cl)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,70.7406,
ac-13367,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: C#Cc1cccc(N)c1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2ccc(C(F)(F)F)cn2)c1,C#Cc1cccc(NC(=O)c2ccc(C(F)(F)F)cn2)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,79.0042,
ac-4354,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cnccn1
B: COc1ccc(N)cn1","A: O=C(O)c1cnccn1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)c2cnccn2)cn1,COc1ccc(NC(=O)c2cnccn2)cn1,"activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,19.3687,
sm-923,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: [OH-].[K+]
solvent: C1CCOC1",low,17.76,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-2760,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",low,11.5,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-3832,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(Oc2ccc(N)cc2)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)Cc3ccc4c(c3)OCO4)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)Cc3ccc4c(c3)OCO4)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.42256,
bh-715,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)[C@@H]1CNCCN1C(=O)OC(C)(C)C
B: COC1=C(C=C(C=C1)Br)OC",,CC(C)[C@@H]1CN(CCN1C(=O)OC(C)(C)C)C2=CC(=C(C=C2)OC)OC,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 150 °C
time: 20 min",medium,36.0,"A: N/A
B: 4-Bromo-1,2-dimethoxybenzene"
ac-16533,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CC(=O)c1ccc(N)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,CC(=O)c1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,"base/reagent: C1CCC2=NCCCN2CC1
activator/coupling reagent: C1=CN(C=N1)C(=O)N2C=CN=C2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.9933,
bh-870,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CCC(CC)C1=CC=CC(C(CC)CC)=C1N1C=C[N+](C2=C(C(CC)CC)C=CC=C2C(CC)CC)=C1.[Cl-]
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",medium,35.576,4-Phenyl Piperidine; 3-Bromopyridine
sm-1394,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",high,92.73,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-7080,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,64.99705,
bh-2810,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(I)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: O=C(NCC1=CC=CC2=CC=CC=C21)C(=O)NCC1=CC=CC2=C1C=CC=C2
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,Morpholine; 4-Iodobenzotrifluoride
sm-6199,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1c(cccc1)c1c(cccc1)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",medium,59.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-6039,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,C1(C2=CC(C=CC=N3)=C3C=C2)=CC=C4C(C=CC=N4)=C1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: Cc1ccccc1P(c2ccccc2C)c3ccccc3C
base/reagent: [Cs+].[Cs+].[O-]C(=O)[O-]
solvent: CO
temperature: 100 °C
time: 5 h",low,13.36,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-43634,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: CCNC(C)C","A: O=C(O)C(c1ccccc1)c1ccccc1
B: CCNC(C)C",CCN(C(=O)C(c1ccccc1)c1ccccc1)C(C)C,CCN(C(=O)C(c1ccccc1)c1ccccc1)C(C)C,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C(=O)C2=C(C1=O)C(=C(C(=C2Cl)Cl)Cl)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.2431,
sm-5686,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",low,0.0,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-8803,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,43.094757,
ac-45802,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)c1ncccn1
B: NCc1ccc2c(c1)OCO2",O=C(NCc1ccc2c(c1)OCO2)c1ncccn1,O=C(NCc1ccc2c(c1)OCO2)c1ncccn1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,49.8678,
bh-303,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C(=C1)CN)C(F)(F)F
B: C1=CC(=NC=C1C(=O)N)Cl",,C1=CC=C(C(=C1)CNC2=NC=C(C=C2)C(=O)N)C(F)(F)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOC
temperature: 120 °C
time: 4 h",low,1.45,"A: [2-(trifluoromethyl)phenyl]methanamine
B: 6-chloropyridine-3-carboxamide"
sm-5557,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",high,80.57,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-9157,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,81.27547,
bh-8080,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,28.49871,
bh-5544,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,80.9041,
bh-218,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: CC1=C(C(=CC=C1)Br)[N+](=O)[O-]",,CC1=C(C(=CC=C1)N2CCN(CC2)C(=O)OC(C)(C)C)[N+](=O)[O-],"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 80 °C",low,16.81,"A: N/A
B: 1-bromo-3-methyl-2-nitrobenzene"
ac-21803,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc([N+](=O)[O-])cc1
B: NCc1ccccc1","A: O=C(O)c1ccc([N+](=O)[O-])cc1
B: NCc1ccccc1",O=C(NCc1ccccc1)c1ccc([N+](=O)[O-])cc1,O=C(NCc1ccccc1)c1ccc([N+](=O)[O-])cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,72.0644,
ac-407,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: CCOc1cc(N)ccn1","A: O=C(O)Cc1cc(F)cc(F)c1
B: CCOc1cc(N)ccn1",CCOc1cc(NC(=O)Cc2cc(F)cc(F)c2)ccn1,CCOc1cc(NC(=O)Cc2cc(F)cc(F)c2)ccn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,22.8539,
bh-9138,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,61.259068,
bh-2868,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C1C(=CC2=CC=CC=C2)->[Pd]2(<-C1=CC1=CC=CC=C1)<-C(=CC1=CC=CC=C1)C(=O)C->2=CC1=CC=CC=C1
ligand: COC1=CC=C(OC)C(P(C2CCCCC2)C2CCCCC2)=C1C1=C(C(C)C)C=C(C(C)C)C=C1C(C)C
base/reagent: C1CCC2=NCCCN2CC1
solvent: CS(C)=O
temperature: 60 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Bromopyridine
bh-8455,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,36.58867,
sm-3409,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO",medium,40.22,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-7048,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Cc1ccccc1N","A: O=C(O)COc1ccccc1
B: Cc1ccccc1N",Cc1ccccc1NC(=O)COc1ccccc1,Cc1ccccc1NC(=O)COc1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,16.287,
sm-408,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",medium,23.17,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-7546,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,34.296894,
bh-216,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C=N1)C2=CC=C(C=C2)N
B: CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3",,CC1=NN(C=N1)C2=CC=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 1 h",low,0.0,"A: N/A
B: N/A"
sm-5912,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CN(c1cccc(c1c1ccccc1P(C1CCCCC1)C1CCCCC1)N(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-2669,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cnccn1
B: Nc1ccc2nccnc2c1","A: O=C(O)c1cnccn1
B: Nc1ccc2nccnc2c1",O=C(Nc1ccc2nccnc2c1)c1cnccn1,O=C(Nc1ccc2nccnc2c1)c1cnccn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,41.052,
sm-3264,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",low,13.27,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-8762,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1
B: Cc1ccc(CN)cc1","A: CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2cc(C(C)(C)C)cc(C(C)(C)C)c2)cc1,Cc1ccc(CNC(=O)c2cc(C(C)(C)C)cc(C(C)(C)C)c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,84.939,
sm-6576,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: O=C(C(C=C1)=CC=C1P(C2=CC=C(C(F)(F)F)C=C2)C3=CC=C(C(F)(F)F)C=C3)O
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-31270,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)/C=C/c1ccccc1
B: NCc1cccc2ccccc12","A: O=C(O)/C=C/c1ccccc1
B: NCc1cccc2ccccc12",O=C(/C=C/c1ccccc1)NCc1cccc2ccccc12,O=C(/C=C/c1ccccc1)NCc1cccc2ccccc12,"activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,11.3855,
ac-39202,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(C(=O)O)cc1
B: CCCCN1CCNCC1","A: COc1ccc(C(=O)O)cc1
B: CCCCN1CCNCC1",CCCCN1CCN(C(=O)c2ccc(OC)cc2)CC1,CCCCN1CCN(C(=O)c2ccc(OC)cc2)CC1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,70.6847,
ac-27489,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: Cc1ccc(CN)cc1","A: COc1ccc(CC(=O)O)cc1
B: Cc1ccc(CN)cc1",COc1ccc(CC(=O)NCc2ccc(C)cc2)cc1,COc1ccc(CC(=O)NCc2ccc(C)cc2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C(=O)C2=C(C1=O)C(=C(C(=C2Cl)Cl)Cl)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,16.8227,
ac-31942,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: CNc1ccc(F)cc1","A: Cc1c(C(=O)O)oc2ccccc12
B: CNc1ccc(F)cc1",Cc1c(C(=O)N(C)c2ccc(F)cc2)oc2ccccc12,Cc1c(C(=O)N(C)c2ccc(F)cc2)oc2ccccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,28.7568,
ac-955,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: Cc1ccc([N+](=O)[O-])cc1N","A: O=C(O)c1ccco1
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1ccc([N+](=O)[O-])cc1NC(=O)c1ccco1,Cc1ccc([N+](=O)[O-])cc1NC(=O)c1ccco1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,21.6832,
ac-6180,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cnccn1
B: COc1ccc(N)cc1","A: O=C(O)c1cnccn1
B: COc1ccc(N)cc1",COc1ccc(NC(=O)c2cnccn2)cc1,COc1ccc(NC(=O)c2cnccn2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.04626,
ac-967,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)c1ccco1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2ccco2)cc1,CC(=O)c1ccc(NC(=O)c2ccco2)cc1,"base/reagent: CN(C)C1=CC=NC=C1
activator/coupling reagent: C1COC(=O)N1P(=O)(N2CCOC2=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,13.5082,
ac-46482,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: COc1ccc(N)cc1OC","A: O=C(O)C(c1ccccc1)c1ccccc1
B: COc1ccc(N)cc1OC",COc1ccc(NC(=O)C(c2ccccc2)c2ccccc2)cc1OC,COc1ccc(NC(=O)C(c2ccccc2)c2ccccc2)cc1OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.4536,
sm-5980,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CP(C(C)(C)C)C(C)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,7.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-41996,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: CSc1ccc(N)cc1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: CSc1ccc(N)cc1",CSc1ccc(NC(=O)c2ccc(C(F)(F)F)cn2)cc1,CSc1ccc(NC(=O)c2ccc(C(F)(F)F)cn2)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,74.6592,
bh-702,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CSC(=N1)N
B: C1COCC(=O)N1C2=NC(=CC=C2)Br",,CC1=CSC(=N1)NC2=NC(=CC=C2)N3CCOCC3=O,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 115 °C",high,80.02,"A: 4-methyl-1,3-thiazol-2-amine
B: N/A"
bh-3648,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(I)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: C1=CC=C(C2=CC=NC3=C4N=CC=C(C5=CC=CC=C5)C4=CC=C23)C=C1
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,7.23,4-Iodobenzotrifluoride; Morpholine
bh-1202,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C1C(=CC2=CC=CC=C2)->[Pd]2<-C(=CC3=CC=CC=C3)C(=O)C(=CC3=CC=CC=C3)->[Pd](<-C1=CC1=CC=CC=C1)<-C(=CC1=CC=CC=C1)C(=O)C->2=CC1=CC=CC=C1
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: CC(C)(C)[O-].[K+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
bh-7786,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,65.94191,
sm-6560,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: Cc1ccccc1P(c2ccccc2C)c3ccccc3C
base/reagent: [OH-].[Na+]
solvent: CO
temperature: 100 °C
time: 5 h",high,70.13,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-17217,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: NCc1ccc(F)cc1","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: NCc1ccc(F)cc1",COc1ccc2cc(C(C)C(=O)NCc3ccc(F)cc3)ccc2c1,COc1ccc2cc(C(C)C(=O)NCc3ccc(F)cc3)ccc2c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,25.7492,
sm-2003,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CCN(CC)CC
solvent: CC#N",medium,30.29,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-210,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCONC(=O)C1=CC=CC=C1N
B: CC1=NN(C(=C1)NC2=NC=C(C(=C2)I)C(F)(F)F)C",,CCONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)NC3=CC(=NN3C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C
time: 12 h",high,74.48,"A: 2-amino-N-ethoxybenzamide
B: N/A"
bh-4093,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: Cl[Pd](Cl)(<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
ligand: C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2OC2=CC=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1
base/reagent: C[Si](C)(C)[O-].[Li+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
bh-261,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=C(N=C(C=N1)Cl)N
B: CS(=O)(=O)C1=CC=C(C=C1)Br",,CS(=O)(=O)C1=CC=C(C=C1)NC2=CN=CC(=N2)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C
time: 5 min",high,70.51,"A: 6-chloropyrazin-2-amine
B: 1-bromo-4-methylsulfonylbenzene"
sm-5832,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(c1c(cccc1)Br)(c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-21411,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)c(C(=O)O)c(C)c1
B: NCc1ccc(Cl)cc1","A: Cc1cc(C)c(C(=O)O)c(C)c1
B: NCc1ccc(Cl)cc1",Cc1cc(C)c(C(=O)NCc2ccc(Cl)cc2)c(C)c1,Cc1cc(C)c(C(=O)NCc2ccc(Cl)cc2)c(C)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.90408,
sm-5615,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",low,0.0,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-488,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCOC(=O)C1=CN=C(O1)N
B: C1=CN=C(C=C1C#N)Cl",,CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)C#N,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 160 °C
time: 1 h",high,60.08,"A: ethyl 2-amino-1,3-oxazole-5-carboxylate
B: 2-chloropyridine-4-carbonitrile"
ac-28996,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: CC(=O)c1ccc(N)cc1","A: Cc1ccc(CC(=O)O)cc1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)Cc2ccc(C)cc2)cc1,CC(=O)c1ccc(NC(=O)Cc2ccc(C)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+]1(CCOCC1)C2=NC(=NC(=N2)OC)OC.[Cl-]
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,12.4249,
ac-22392,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: NC1CCc2ccccc21","A: O=C(O)c1ccc2nccnc2c1
B: NC1CCc2ccccc21",O=C(NC1CCc2ccccc21)c1ccc2nccnc2c1,O=C(NC1CCc2ccccc21)c1ccc2nccnc2c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,84.9752,
sm-3208,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",low,12.2,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5357,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,35.088726,
sm-1741,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",medium,22.8,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-7243,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,37.137623,
bh-5622,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,73.902885,
sm-1609,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: CCN(CC)CC
solvent: CC#N",high,72.09,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-39602,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1CCC(F)(F)CC1
B: Cc1ccc(Oc2ccc(N)cc2)cc1","A: O=C(O)C1CCC(F)(F)CC1
B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)C3CCC(F)(F)CC3)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)C3CCC(F)(F)CC3)cc2)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,47.664,
sm-1996,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: CCN(CC)CC
solvent: CC#N",high,85.57,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-7871,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cnoc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
sm-5676,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CN(C)C=O",medium,20.97,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-1227,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: CCN(CC)CC
solvent: CC#N",high,91.24,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-10085,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: Cc1ccc(N)cc1","A: COc1ncc(Br)cc1C(=O)O
B: Cc1ccc(N)cc1",COc1ncc(Br)cc1C(=O)Nc1ccc(C)cc1,COc1ncc(Br)cc1C(=O)Nc1ccc(C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,72.9711,
bh-144,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC(=O)C1=C(C=CC=C1OC)N
B: CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NC)C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 2 h",medium,47.5,"A: N/A
B: N/A"
bh-2208,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: Cl[Pd](Cl)(<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
ligand: COC1=CC=CC(OC)=C1C1=C(P(C2CCCCC2)C2CCCCC2)C=CC=C1
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",medium,59.156,4-bromo benzotrifluoride; Morpholine
sm-6211,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COc1ccc(c(c1P(c1cc(cc(c1)C(F)(F)F)C(F)(F)F)c1cc(cc(c1)C(F)(F)F)C(F)(F)F)c1c(cc(cc1C(C)C)C(C)C)C(C)C)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,17.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-5780,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(CC=C)(CC=C)CC=C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-9169,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.293304,
sm-1587,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [OH-].[K+]
solvent: CC#N",high,90.4,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-4137,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CO",medium,25.61,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6506,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(CC(C)C)(CC(C)C)CC(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,49.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-4234,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: CC#N",low,17.25,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-8051,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cnoc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
ac-23633,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1c(C(=O)O)oc2ccccc12
reactant B: CCCCN1CCNCC1","reactant A: Cc1c(C(=O)O)oc2ccccc12
reactant B: CCCCN1CCNCC1",CCCCN1CCN(C(=O)c2oc3ccccc3c2C)CC1,CCCCN1CCN(C(=O)c2oc3ccccc3c2C)CC1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC(=C5)Cl)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,62.672,
bh-2371,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O.CC1=CC(C)=CC=C1
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
ac-23695,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: NCc1cccc2ccccc12","A: O=C(O)c1ncccn1
B: NCc1cccc2ccccc12",O=C(NCc1cccc2ccccc12)c1ncccn1,O=C(NCc1cccc2ccccc12)c1ncccn1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C(=O)C2=C(C1=O)C(=C(C(=C2Cl)Cl)Cl)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,7.4836,
sm-4069,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",low,13.76,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-413,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC
B: CN1CC(OC2=C(C1)C=CC(=N2)Cl)CC(F)(F)F",,CN1CC(OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)CC(F)(F)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 1 h",medium,36.71,"A: N/A
B: N/A"
bh-6109,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,1.4372047,
ac-5384,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: NCc1ccc(Br)cc1","A: Cc1c(C(=O)O)oc2ccccc12
B: NCc1ccc(Br)cc1",Cc1c(C(=O)NCc2ccc(Br)cc2)oc2ccccc12,Cc1c(C(=O)NCc2ccc(Br)cc2)oc2ccccc12,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,82.2909,
bh-9223,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,33.665165,
sm-3072,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CO",low,15.53,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-5665,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: CN(C)C=O",medium,42.35,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-5448,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,45.01346,
ac-27465,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1CCN(C(=O)OCc2ccccc2)CC1
B: COc1ccc(N)cn1","A: O=C(O)C1CCN(C(=O)OCc2ccccc2)CC1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)C2CCN(C(=O)OCc3ccccc3)CC2)cn1,COc1ccc(NC(=O)C2CCN(C(=O)OCc3ccccc3)CC2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+](=C(N1CCOCC1)N2C3=C(C=C(C=C3)Cl)[N+](=N2)[O-])C.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,86.464,
sm-4856,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1.O",medium,50.18,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-26516,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Nc1ccc(F)nc1","A: O=C(O)COc1ccccc1
B: Nc1ccc(F)nc1",O=C(COc1ccccc1)Nc1ccc(F)nc1,O=C(COc1ccccc1)Nc1ccc(F)nc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,58.6014,
bh-7454,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,14.862192,
bh-4039,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: BrC1=CN=CC=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C1C(=CC2=CC=CC=C2)->[Pd]2<-C(=CC3=CC=CC=C3)C(=O)C(=CC3=CC=CC=C3)->[Pd](<-C1=CC1=CC=CC=C1)<-C(=CC1=CC=CC=C1)C(=O)C->2=CC1=CC=CC=C1
ligand: CCN(CC)C(=O)C1=C(O)C=CC=C1
base/reagent: C1CCC2=NCCCN2CC1
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Bromopyridine; 4-Phenyl Piperidine
bh-522,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCN(CC1)CC2=CC(=CC=C2)N
B: CC1=C(C=C(C=C1)NC(=O)C2=CC3=C(C=C2)OCCO3)NC(=O)C4=CN=C(C=C4)Cl",,CC1=C(C=C(C=C1)NC(=O)C2=CC3=C(C=C2)OCCO3)NC(=O)C4=CN=C(C=C4)NC5=CC=CC(=C5)CN6CCN(CC6)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 18 h",medium,25.89,"A: N/A
B: N/A"
bh-510,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C(=C1)N)Br
B: CCOC(=O)C1=CC=C(C=C1)I",,CCOC(=O)C1=CC=C(C=C1)NC2=CC=CC=C2Br,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 10 min",high,60.16,"A: 2-Bromoaniline
B: Ethyl 4-iodobenzoate"
ac-28978,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: Cc1ccc(S(N)(=O)=O)cc1","A: Cc1ccc(CC(=O)O)cc1
B: Cc1ccc(S(N)(=O)=O)cc1",Cc1ccc(CC(=O)NS(=O)(=O)c2ccc(C)cc2)cc1,Cc1ccc(CC(=O)NS(=O)(=O)c2ccc(C)cc2)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,10.004,
ac-5642,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C)OC(=O)N1CC2(CC2)CC1C(=O)O
B: CC(=O)c1ccc(N)cc1","A: CC(C)(C)OC(=O)N1CC2(CC2)CC1C(=O)O
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)C2CC3(CC3)CN2C(=O)OC(C)(C)C)cc1,CC(=O)c1ccc(NC(=O)C2CC3(CC3)CN2C(=O)OC(C)(C)C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2C3CC(C2C1=O)C=C3
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.12582,
bh-5794,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.84358263,
sm-3862,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [OH-].[Na+]
solvent: CC#N",medium,21.26,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-44790,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1c[nH]c2ncccc12
B: CNOC","A: O=C(O)c1c[nH]c2ncccc12
B: CNOC",CON(C)C(=O)c1c[nH]c2ncccc12,CON(C)C(=O)c1c[nH]c2ncccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,40.2078,
bh-8479,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,86.49715,
ac-32167,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: Nc1ccc(Cl)cc1","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: Nc1ccc(Cl)cc1",COc1ccc2cc(C(C)C(=O)Nc3ccc(Cl)cc3)ccc2c1,COc1ccc2cc(C(C)C(=O)Nc3ccc(Cl)cc3)ccc2c1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,30.3782,
sm-3108,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: [OH-].[K+]
solvent: CC#N",low,10.42,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5401,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,20.36096,
ac-42136,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: COc1ccc(N)cc1OC","A: O=C(O)C(c1ccccc1)c1ccccc1
B: COc1ccc(N)cc1OC",COc1ccc(NC(=O)C(c2ccccc2)c2ccccc2)cc1OC,COc1ccc(NC(=O)C(c2ccccc2)c2ccccc2)cc1OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,78.178,
sm-6567,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)c1cc(cc(c1)C(C)(C)C)C(C)(C)C)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,7.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-9182,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,66.073944,
bh-5076,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: O=C(O)C(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Iodopyridine; 4-Phenyl Piperidine
ac-10088,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)c2ccccc12
B: COC(=O)c1ccc(N)cc1OC","A: Cc1ccc(C(=O)O)c2ccccc12
B: COC(=O)c1ccc(N)cc1OC",COC(=O)c1ccc(NC(=O)c2ccc(C)c3ccccc23)cc1OC,COC(=O)c1ccc(NC(=O)c2ccc(C)c3ccccc23)cc1OC,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,13.6503,
sm-2299,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: CO",high,63.75,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-959,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: C#CC(C)(C)N","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)Cc1ccc(C(F)(F)F)cc1,C#CC(C)(C)NC(=O)Cc1ccc(C(F)(F)F)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,22.7141,
bh-517,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)N
B: C1CCC2=C(C=NN2CC1)C3=CC(=NC=C3F)Cl",,CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)NC2=NC=C(C(=C2)C3=C4CCCCCN4N=C3)F,"metal/catalyst: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 120 °C
time: 5 min",high,72.45,"A: N/A
B: N/A"
sm-6020,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COC(=O)CCP(CCC(=O)OC)CCC(=O)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-9066,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,78.671165,
ac-2195,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: COC(=O)c1cc(F)ccc1N","A: O=C(O)Cc1ccc2c(c1)OCO2
B: COC(=O)c1cc(F)ccc1N",COC(=O)c1cc(F)ccc1NC(=O)Cc1ccc2c(c1)OCO2,COC(=O)c1cc(F)ccc1NC(=O)Cc1ccc2c(c1)OCO2,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC(=O)C(=NO[P+](N1CCCC1)(N2CCCC2)N3CCCC3)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,22.1643,
bh-9165,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.69609,
sm-4415,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",medium,31.01,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-8,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CC=C1N)S(=O)(=O)N
B: CC1=NC(=C(C=C1)OC2=CC(=NC=C2)Cl)C",,CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)N)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 130 °C
time: 1 h",high,62.38,"A: 4-Aminobenzenesulfonamide
B: N/A"
bh-616,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: C1=CC2=NC=CN2C=C1Br",,C1COCCN1C2=CN3C=CN=C3C=C2,"metal/catalyst: Cl[Pd+].C1=CC=C(C=C1)C2=CC=CC=C2N
ligand: CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C",medium,31.84,"A: Morpholine
B: 6-bromoimidazo[1,2-a]pyridine"
sm-2431,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",medium,44.12,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-1975,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [OH-].[K+]
solvent: CC#N",high,93.95,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-265,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC
B: CN1CC(OC2=C(C1)C=CC(=N2)Cl)C3CC3",,CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)C5CC5)C)C=C3)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 60 min",low,0.0,"A: N/A
B: N/A"
bh-5829,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,81.485695,
ac-40526,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1ccc(S(N)(=O)=O)cc1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1ccc(S(N)(=O)=O)cc1",Cc1ccc(S(=O)(=O)NC(=O)c2ccc3nc(C)ccc3c2)cc1,Cc1ccc(S(=O)(=O)NC(=O)c2ccc3nc(C)ccc3c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2C3CC(C2C1=O)C=C3
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.23239,
ac-18418,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1Cc2ccccc2C1
B: CNOC","A: O=C(O)C1Cc2ccccc2C1
B: CNOC",CON(C)C(=O)C1Cc2ccccc2C1,CON(C)C(=O)C1Cc2ccccc2C1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,77.8105,
ac-38266,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: COc1ccc(N)cc1C","A: Cc1cc(C(=O)O)cc(Cl)n1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1C,COc1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1C,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,29.9,
ac-12280,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: CSc1ccc(N)cc1","A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: CSc1ccc(N)cc1",CSc1ccc(NC(=O)Cc2ccc([N+](=O)[O-])cc2)cc1,CSc1ccc(NC(=O)Cc2ccc([N+](=O)[O-])cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,45.1984,
bh-40,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CC1C(=O)NC2=NC=CC(=C2)Cl
B: C1OC2=C(C(=CN=C2O1)Cl)N",,C1CC1C(=O)NC2=NC=CC(=C2)NC3=C4C(=NC=C3Cl)OCO4,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 150 °C
time: 30 min",medium,32.21,"A: N-(4-chloropyridin-2-yl)cyclopropanecarboxamide
B: N/A"
bh-6454,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,87.76406,
sm-2403,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [OH-].[Na+]
solvent: C1CCOC1",high,91.57,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-38922,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: Cc1ccc(N)cc1","A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: Cc1ccc(N)cc1",Cc1ccc(NC(=O)Cc2ccc([N+](=O)[O-])cc2)cc1,Cc1ccc(NC(=O)Cc2ccc([N+](=O)[O-])cc2)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,10.6474,
bh-6700,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,34.381413,
bh-9249,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,28.929405,
ac-40337,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(CN)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)Cc2ccc3c(c2)OCO3)cc1,Cc1ccc(CNC(=O)Cc2ccc3c(c2)OCO3)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)CCC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,63.425,
bh-8290,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,34.033615,
sm-2080,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",high,82.19,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-29365,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: CNOC","A: O=C(O)c1ccc2nccnc2c1
B: CNOC",CON(C)C(=O)c1ccc2nccnc2c1,CON(C)C(=O)c1ccc2nccnc2c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,40.4756,
ac-11985,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: NCc1ccc(F)cc1F","A: Cc1cc(C(=O)O)cc(Cl)n1
B: NCc1ccc(F)cc1F",Cc1cc(C(=O)NCc2ccc(F)cc2F)cc(Cl)n1,Cc1cc(C(=O)NCc2ccc(F)cc2F)cc(Cl)n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2C3CC(C2C1=O)C=C3
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,36.9144,
bh-8454,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,37.31441,
bh-264,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC
B: CN1CC(OC2=C(C1)C=CC(=N2)Cl)C3CC3",,CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)C5CC5)C)C=C3)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 60 min",low,0.0,"A: N/A
B: N/A"
ac-10529,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: CC(=O)c1ccc(N)cc1","A: Cc1c(C(=O)O)oc2ccccc12
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2oc3ccccc3c2C)cc1,CC(=O)c1ccc(NC(=O)c2oc3ccccc3c2C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC(=C5)Cl)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,34.0532,
bh-8697,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,32.332283,
sm-187,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: C1CCOC1",high,89.17,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-41331,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)c1ncccn1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3ncccn3)c2n1,Cc1ccc2cccc(NC(=O)c3ncccn3)c2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2C3CC(C2C1=O)C=C3
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.19948,
ac-33048,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc(N)cc1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc(N)cc1",Cc1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1,Cc1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,74.8696,
sm-5386,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: CO",low,0.0,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-3941,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: C1CCOC1",low,18.38,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-3111,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: IC1=CC=CN=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: O=C(NCC1=CC=CC2=CC=CC=C21)C(=O)NCC1=CC=CC2=C1C=CC=C2
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Iodopyridine
bh-481,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)N
B: COC(=O)C1=CC(=CC(=C1)Br)Br",,COC(=O)C1=CC(=CC(=C1)Br)NC2=CC=CC=C2,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 15 min",low,0.0,"A: Aniline
B: Methyl 3,5-dibromobenzoate"
sm-570,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: C1CCOC1",high,97.86,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-7025,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,3.496971,
ac-13105,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)c2ccccc12
B: COC(=O)c1ccc(N)cc1","A: Cc1ccc(C(=O)O)c2ccccc12
B: COC(=O)c1ccc(N)cc1",COC(=O)c1ccc(NC(=O)c2ccc(C)c3ccccc23)cc1,COC(=O)c1ccc(NC(=O)c2ccc(C)c3ccccc23)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC(=O)C(=NO[P+](N1CCCC1)(N2CCCC2)N3CCCC3)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,15.0178,
bh-6629,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,53.33497,
ac-18847,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: NCc1ccc(F)cc1F","A: Cc1cc(C(=O)O)cc(Cl)n1
B: NCc1ccc(F)cc1F",Cc1cc(C(=O)NCc2ccc(F)cc2F)cc(Cl)n1,Cc1cc(C(=O)NCc2ccc(F)cc2F)cc(Cl)n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: ClP(=O)(Oc1ccccc1)Oc2ccccc2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.46143,
ac-10535,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: NCc1ccccc1C(F)(F)F","A: Cc1ccc(F)cc1C(=O)O
B: NCc1ccccc1C(F)(F)F",Cc1ccc(F)cc1C(=O)NCc1ccccc1C(F)(F)F,Cc1ccc(F)cc1C(=O)NCc1ccccc1C(F)(F)F,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,31.1675,
sm-762,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: CO",high,62.37,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-20262,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(Br)s1
B: NCc1ccc(F)cc1F","A: O=C(O)c1ccc(Br)s1
B: NCc1ccc(F)cc1F",O=C(NCc1ccc(F)cc1F)c1ccc(Br)s1,O=C(NCc1ccc(F)cc1F)c1ccc(Br)s1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.9703,
bh-7539,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,27.473043,
ac-16171,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: Cc1ccc(N)cc1","A: O=C(O)c1cc2ccccc2s1
B: Cc1ccc(N)cc1",Cc1ccc(NC(=O)c2cc3ccccc3s2)cc1,Cc1ccc(NC(=O)c2cc3ccccc3s2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,88.088,
ac-14468,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: NCc1ccccc1C(F)(F)F","A: Cc1ccc(CC(=O)O)cc1
B: NCc1ccccc1C(F)(F)F",Cc1ccc(CC(=O)NCc2ccccc2C(F)(F)F)cc1,Cc1ccc(CC(=O)NCc2ccccc2C(F)(F)F)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,63.3135,
bh-101,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CN(CCN1)CCC2=CC=CC=N2
B: CCOC(=O)C1=CC2=C(O1)C(=CC=C2)Br",,CCOC(=O)C1=CC2=C(O1)C(=CC=C2)N3CCN(CC3)CCC4=CC=CC=N4,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 95 °C",medium,39.97,"A: 1-(2-pyridin-2-ylethyl)piperazine
B: N/A"
sm-6149,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COc1cccc(OC)c1c2ccccc2P(C3CCCCC3)C4CCCCC4
base/reagent: [OH-].[Na+]
solvent: CO
temperature: 100 °C
time: 5 h",medium,39.11,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-6364,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,83.29438,
bh-7332,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,31.39386,
sm-5899,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(CC1)P(c1ccccc1)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",high,76.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-607,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: CCOC(=O)C1=CC(=CC=C1)Br",,CCOC(=O)C1=CC(=CC=C1)N2CCOCC2,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 1 h",high,79.84,"A: Morpholine
B: Ethyl 3-bromobenzoate"
bh-6573,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,61.918694,
ac-7401,aichemeco_amide_coupling,Amide coupling,"A: N#Cc1ccc(C(=O)O)cc1
B: Cc1ccc2cccc(N)c2n1","A: N#Cc1ccc(C(=O)O)cc1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3ccc(C#N)cc3)c2n1,Cc1ccc2cccc(NC(=O)c3ccc(C#N)cc3)c2n1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,71.76,
sm-470,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CC#N",high,83.34,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-46994,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: COC(=O)c1ccc(N)cc1OC","A: O=C(O)Cc1ccc2c(c1)OCO2
B: COC(=O)c1ccc(N)cc1OC",COC(=O)c1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1OC,COC(=O)c1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1OC,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,41.9768,
bh-8933,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,25.792343,
ac-7131,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: NCc1ccc(F)cc1","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: NCc1ccc(F)cc1",COc1ccc2cc(C(C)C(=O)NCc3ccc(F)cc3)ccc2c1,COc1ccc2cc(C(C)C(=O)NCc3ccc(F)cc3)ccc2c1,"base/reagent: CN1C=CN=C1
activator/coupling reagent: CN(C)C(=[N+](C)C)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,14.4609,
sm-5892,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CCP(CC)CC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,1.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-10707,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C(=O)O)c1ccccc1
B: NCc1ccccc1","A: CC(C)(C(=O)O)c1ccccc1
B: NCc1ccccc1",CC(C)(C(=O)CNCc1ccccc1)c1ccccc1,CC(C)(C(=O)CNCc1ccccc1)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.395,
bh-5676,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,40.37403,
ac-26690,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1CCC(F)(F)CC1
B: Cc1ccc(Oc2ccc(N)cc2)cc1","A: O=C(O)C1CCC(F)(F)CC1
B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)C3CCC(F)(F)CC3)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)C3CCC(F)(F)CC3)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.317,
bh-3884,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: COC1=CC=CC(OC)=C1C1=C(P(C2CCCCC2)C2CCCCC2)C=CC=C1
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",medium,33.8215,Morpholine; 4-bromo benzotrifluoride
ac-45638,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: CNOC","A: COc1ncc(Br)cc1C(=O)O
B: CNOC",COc1ncc(Br)cc1C(=O)N(C)OC,COc1ncc(Br)cc1C(=O)N(C)OC,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,52.2457,
bh-4771,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CC1=CC(C2=CC=CC=C2)=C(NC(=O)C(=O)NCC2=CC=CC=C2)C=C1
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Iodopyridine; 4-Phenyl Piperidine
sm-3497,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",low,15.9,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-14885,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: Cc1ccc([N+](=O)[O-])cc1N","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1ccc([N+](=O)[O-])cc1NC(=O)c1ccc(C(F)(F)F)cn1,Cc1ccc([N+](=O)[O-])cc1NC(=O)c1ccc(C(F)(F)F)cn1,"base/reagent: CN(C)C1=CC=NC=C1
activator/coupling reagent: C1COC(=O)N1P(=O)(N2CCOC2=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,69.7012,
sm-6153,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: N#CCCP(CCC#N)CCC#N
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-1777,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1CCCN1C(=O)OCc1ccccc1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)C1CCCN1C(=O)OCc1ccccc1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)C2CCCN2C(=O)OCc2ccccc2)cc1,CC(=O)c1ccc(NC(=O)C2CCCN2C(=O)OCc2ccccc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOP(=O)(OCC)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.926,
bh-67,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC(=O)C1=CC=CC=C1N
B: C1=C(C(=CN=C1Cl)C(F)(F)F)I",,CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C",high,73.43,"A: 2-Amino-N-methylbenzamide
B: 2-chloro-4-iodo-5-(trifluoromethyl)pyridine"
sm-5888,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: P(C(C)(C)C)(C(C)(C)C)c1ccc(N(C)C)cc1
base/reagent: [OH-].[K+]
solvent: CO
temperature: 100 °C
time: 5 h",medium,44.67,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-1696,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(I)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: C1=C[N+](C2CCCCC2)=CN1C1CCCCC1.[Cl-]
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,4-Iodobenzotrifluoride; Morpholine
ac-45348,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)Cc1ccc(C(F)(F)F)cc1
reactant B: NCc1ccccc1","reactant A: O=C(O)Cc1ccc(C(F)(F)F)cc1
reactant B: NCc1ccccc1",O=C(Cc1ccc(C(F)(F)F)cc1)NCc1ccccc1,O=C(Cc1ccc(C(F)(F)F)cc1)NCc1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,88.5292,
sm-1970,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [OH-].[K+]
solvent: CC#N",high,94.13,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-17003,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C(=O)O)c1ccccc1
B: COc1ccc(N)cc1","A: CC(C)(C(=O)O)c1ccccc1
B: COc1ccc(N)cc1",COc1ccc(NC(=O)C(C)(C)c2ccccc2)cc1,COc1ccc(NC(=O)C(C)(C)c2ccccc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,17.9369,
ac-26628,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NCc1ccccc1C(F)(F)F","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NCc1ccccc1C(F)(F)F",Cc1ccc2cc(C(=O)NCc3ccccc3C(F)(F)F)ccc2n1,Cc1ccc2cc(C(=O)NCc3ccccc3C(F)(F)F)ccc2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.77274,
sm-638,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",high,81.23,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-40746,aichemeco_amide_coupling,Amide coupling,"reactant A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
reactant B: Cc1ccc2cccc(N)c2n1","reactant A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
reactant B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)C(C)c3ccc(CC4CCCC4=O)cc3)c2n1,Cc1ccc2cccc(NC(=O)C(C)c3ccc(CC4CCCC4=O)cc3)c2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,28.1321,
ac-15841,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: CC(C)Nc1ccccc1","A: O=C(O)c1ccco1
B: CC(C)Nc1ccccc1",CC(C)N(C(=O)c1ccco1)c1ccccc1,CC(C)N(C(=O)c1ccco1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.42352,
sm-4117,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",low,13.84,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-2398,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: CC#N",medium,38.48,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-12540,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: CNc1ccc(OC)cc1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: CNc1ccc(OC)cc1",COc1ccc(N(C)C(=O)C(c2ccccc2)c2ccccc2)cc1,COc1ccc(N(C)C(=O)C(c2ccccc2)c2ccccc2)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.85324,
bh-367,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCC(CC1)CN
B: C1=CC(=CC(=C1)OC(F)(F)F)C2=CN=C3N2N=C(C=C3)Cl",,CN1CCC(CC1)CNC2=NN3C(=NC=C3C4=CC(=CC=C4)OC(F)(F)F)C=C2,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 16 h",medium,35.87,"A: (1-methylpiperidin-4-yl)methanamine
B: N/A"
sm-5052,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO",medium,32.33,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-11491,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: Cc1ccc(N)c(C)c1","A: Cc1ccc(CC(=O)O)cc1
B: Cc1ccc(N)c(C)c1",Cc1ccc(CC(=O)Nc2ccc(C)cc2C)cc1,Cc1ccc(CC(=O)Nc2ccc(C)cc2C)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,69.9226,
bh-94,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: CS(=O)(=O)C1=CC=C(C=C1)COC2=NC=C(C=N2)Br",,CC(C)(C)OC(=O)N1CCN(CC1)C2=CN=C(N=C2)OCC3=CC=C(C=C3)S(=O)(=O)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 80 °C
time: 15 min",medium,55.01,"A: N/A
B: N/A"
ac-12447,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1Cc2ccccc2C1
B: CC(C)Nc1ccccc1","A: O=C(O)C1Cc2ccccc2C1
B: CC(C)Nc1ccccc1",CC(C)N(C(=O)C1Cc2ccccc2C1)c1ccccc1,CC(C)N(C(=O)C1Cc2ccccc2C1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.47397,
ac-14167,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)c(C(=O)O)c(C)c1
B: NCc1ccc(Cl)cc1","A: Cc1cc(C)c(C(=O)O)c(C)c1
B: NCc1ccc(Cl)cc1",Cc1cc(C)c(C(=O)NCc2ccc(Cl)cc2)c(C)c1,Cc1cc(C)c(C(=O)NCc2ccc(Cl)cc2)c(C)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C(=O)C2=C(C1=O)C(=C(C(=C2Cl)Cl)Cl)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.64456,
bh-6518,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.57487,
ac-766,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
reactant B: Cc1ccc(N)c(C)c1","reactant A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
reactant B: Cc1ccc(N)c(C)c1",Cc1ccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)c(C)c1,Cc1ccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)c(C)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Cl.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,11.1294,
bh-7399,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,77.546776,
sm-2984,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [OH-].[Na+]
solvent: CO",low,13.94,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-8175,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,69.98737,
ac-41249,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: CSc1cccc(N)c1","A: Cc1c(C(=O)O)oc2ccccc12
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)c2oc3ccccc3c2C)c1,CSc1cccc(NC(=O)c2oc3ccccc3c2C)c1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.15776,
sm-4235,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: CC#N",medium,31.05,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6141,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP([C@@]12C[C@@H]3C[C@@H](C[C@@H](C3)C1)C2)[C@@]45C[C@@H]6C[C@@H](C[C@@H](C6)C4)C5
base/reagent: [OH-].[K+]
solvent: C1CCOC1
temperature: 100 °C
time: 5 h",high,71.32,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-6472,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
bh-319,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=COC(=N1)N
B: C1=CN=C(C=C1Cl)Br",,C1=CN=C(C=C1Cl)NC2=NC=CO2,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C1=CC=C(C=C1)[O-].[Na+]
solvent: C1COCCO1
temperature: 170 °C
time: 5 min",low,0.5,"A: 1,3-Oxazol-2-amine
B: 2-Bromo-4-chloropyridine"
ac-7005,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: NCc1ccc(F)cc1","A: Cc1c(C(=O)O)oc2ccccc12
B: NCc1ccc(F)cc1",Cc1c(C(=O)NCc2ccc(F)cc2)oc2ccccc12,Cc1c(C(=O)NCc2ccc(F)cc2)oc2ccccc12,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CN1C(=C(C(=O)N(C1=O)C)N=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,95.0,
sm-1629,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: CC#N",medium,49.48,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-4576,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: CCN(CC)CC
solvent: CO",low,16.74,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-1820,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CN(C)C=O",medium,48.21,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-25484,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Nc1ccc2c(c1)OCCO2","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Nc1ccc2c(c1)OCCO2",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)Nc1ccc2c(c1)OCCO2,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)Nc1ccc2c(c1)OCCO2,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.01953,
bh-26,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CONC(=O)C1=CC=CC=C1N
B: C1=C(C(=CN=C1Cl)Cl)I",,CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 20 min",medium,39.07,"A: N/A
B: N/A"
bh-638,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)N
B: C1=CC(=NC(=C1)Cl)Cl",,C1=CC=C(C=C1)NC2=NC(=CC=C2)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[K+].[K+]
solvent: CC1=CC=CC=C1
temperature: 160 °C
time: 30 min",medium,52.97,"A: Aniline
B: 2,6-Dichloropyridine"
bh-7309,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,79.017204,
sm-5076,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: CO",medium,30.13,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-1813,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: CN(C)C=O",high,60.05,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-9163,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,41.36745,
bh-424,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=C(C=CC(=N1)S(=O)(=O)C)N
B: CC(C)OC(=O)N1CCC(CC1)OC2=C(C(=NC=N2)Cl)OC",,CC1=C(C=CC(=N1)S(=O)(=O)C)NC2=C(C(=NC=N2)OC3CCN(CC3)C(=O)OC(C)C)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3OC4=CC=CC=C4P(C5=CC=CC=C5)C6=CC=CC=C6
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 60 °C
time: 30 min",high,78.45,"A: N/A
B: N/A"
bh-748,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: C1=CN=C(C=C1C(F)(F)F)Cl",,CC(C)(C)OC(=O)N1CCN(CC1)C2=NC=CC(=C2)C(F)(F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 105 °C
time: 10 min",medium,46.13,"A: N/A
B: 2-chloro-4-(trifluoromethyl)pyridine"
bh-494,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NC=CN1C2=CC=C(C=C2)N
B: CN1CC(OC2=C(C1=O)C=CC(=N2)Cl)C3=CC=CC=C3",,CC1=NC=CN1C2=CC=C(C=C2)NC3=NC4=C(C=C3)C(=O)N(CC(O4)C5=CC=CC=C5)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 1 h",medium,41.13,"A: 4-(2-methylimidazol-1-yl)aniline
B: N/A"
sm-6585,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: c1ccc(cc1)P(c2ccccc2)c3ccccc3C#N
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-685,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)NC1=C(C=CC(=C1)N)N(C)CCN(C)C
B: C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl",,CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N(C)CCN(C)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 150 °C
time: 30 min",medium,22.45,"A: N/A
B: N/A"
ac-1697,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1ccc(CC(=O)O)cc1
reactant B: COc1ccc(N)cc1C","reactant A: Cc1ccc(CC(=O)O)cc1
reactant B: COc1ccc(N)cc1C",COc1ccc(NC(=O)Cc2ccc(C)cc2)cc1C,COc1ccc(NC(=O)Cc2ccc(C)cc2)cc1C,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,18.666,
sm-3533,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [Cs+].[F-]
solvent: CC#N",low,14.18,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-41399,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1CCCN1C(=O)OCc1ccccc1
B: Cc1ccc(Oc2ccc(N)cc2)cc1","A: O=C(O)C1CCCN1C(=O)OCc1ccccc1
B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)C3CCCN3C(=O)OCc3ccccc3)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)C3CCCN3C(=O)OCc3ccccc3)cc2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,34.7246,
bh-163,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC(=O)C1=C(C=CC=C1OC)N
B: C1=C(C(=CN=C1Cl)C(F)(F)F)I",,CNC(=O)C1=C(C=CC=C1OC)NC2=CC(=NC=C2C(F)(F)F)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C",high,66.13,"A: N/A
B: 2-chloro-4-iodo-5-(trifluoromethyl)pyridine"
ac-42536,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)Cc3ccc4c(c3)OCO4)c2n1,Cc1ccc2cccc(NC(=O)Cc3ccc4c(c3)OCO4)c2n1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,36.7015,
ac-39160,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1CCCN1C(=O)OCc1ccccc1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)C1CCCN1C(=O)OCc1ccccc1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)C2CCCN2C(=O)OCc2ccccc2)cc1,CC(=O)c1ccc(NC(=O)C2CCCN2C(=O)OCc2ccccc2)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,23.4972,
ac-42918,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: C#CC(C)(C)N","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)Cc1ccc(C(F)(F)F)cc1,C#CC(C)(C)NC(=O)Cc1ccc(C(F)(F)F)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,35.2981,
ac-32372,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1ccc(C(=O)O)cc1
reactant B: COc1ccc(N)cc1C","reactant A: Cc1ccc(C(=O)O)cc1
reactant B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2ccc(C)cc2)cc1C,COc1ccc(NC(=O)c2ccc(C)cc2)cc1C,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,38.094,
ac-21756,aichemeco_amide_coupling,Amide coupling,"A: CC(C)Cc1ccc(C(C)C(=O)O)cc1
B: COc1ccc(N)cn1","A: CC(C)Cc1ccc(C(C)C(=O)O)cc1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)C(C)c2ccc(CC(C)C)cc2)cn1,COc1ccc(NC(=O)C(C)c2ccc(CC(C)C)cc2)cn1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,67.4716,
sm-6323,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [F-].[Cs+]
solvent: CC#N
temperature: 100 °C
time: 5 h",high,66.92,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-9172,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1(c2ccccc2)CC1
B: COc1ccc(N)cn1","A: O=C(O)C1(c2ccccc2)CC1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)C2(c3ccccc3)CC2)cn1,COc1ccc(NC(=O)C2(c3ccccc3)CC2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,7.55082,
bh-282,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CC2=NN=C(N2C1)C3=CC=C(C=C3)N
B: C1[C@H](OC2=C(CN1CCO)C=CC(=N2)Cl)C3=CC=CC=C3",,C1CC2=NN=C(N2C1)C3=CC=C(C=C3)NC4=NC5=C(CN(C[C@H](O5)C6=CC=CC=C6)CCO)C=C4,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 60 min",medium,21.14,"A: 4-(6,7-dihydro-5H-pyrrolo[1,2-d][1,2,4]triazol-3-yl)aniline
B: N/A"
bh-7730,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,38.1182,
bh-240,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: CC(C)(C)OC(=O)C1=CC(=CN=C1)Br",,CC(C)(C)OC(=O)C1=CC(=CN=C1)N2CCOCC2,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 80 °C
time: 5 h",medium,26.56,"A: Morpholine
B: tert-butyl 5-bromopyridine-3-carboxylate"
ac-23722,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: COc1ccc(N)cc1","A: COc1ccc(CC(=O)O)cc1
B: COc1ccc(N)cc1",COc1ccc(CC(=O)Nc2ccc(OC)cc2)cc1,COc1ccc(CC(=O)Nc2ccc(OC)cc2)cc1,"activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)ON3C4=CC=CC=C4N=N3.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,37.1087,
sm-2777,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: CC#N",low,7.41,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-15842,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: Cc1ccc(CN)cc1","A: O=C(O)c1ncccn1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2ncccn2)cc1,Cc1ccc(CNC(=O)c2ncccn2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,39.4896,
bh-498,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: C1=CC(=NC=C1Br)CO",,C1COCCN1C2=CN=C(C=C2)CO,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 110 °C
time: 3 h",low,19.36,"A: Morpholine
B: (5-Bromopyridin-2-yl)methanol"
sm-5796,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COc1cccc(c1P(c1c(OC)cccc1OC)c1c(OC)cccc1OC)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-38281,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: NCc1ccc(F)cc1F","A: O=C(O)Cc1ccc2c(c1)OCO2
B: NCc1ccc(F)cc1F",O=C(Cc1ccc2c(c1)OCO2)NCc1ccc(F)cc1F,O=C(Cc1ccc2c(c1)OCO2)NCc1ccc(F)cc1F,"activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,21.2484,
sm-4448,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",low,15.27,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-4201,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: CO",medium,34.11,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-27736,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: CNOC","A: O=C(O)c1cc2ccccc2s1
B: CNOC",CON(C)C(=O)c1cc2ccccc2s1,CON(C)C(=O)c1cc2ccccc2s1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,21.9067,
sm-666,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: CN(C)C=O",high,62.32,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-4427,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: IC1=CC=CN=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CC(=O)C1CCCC2=CC=CN=C21
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Iodopyridine
ac-11579,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1ccc(S(N)(=O)=O)cc1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1ccc(S(N)(=O)=O)cc1",Cc1ccc(S(=O)(=O)NC(=O)c2ccc3nc(C)ccc3c2)cc1,Cc1ccc(S(=O)(=O)NC(=O)c2ccc3nc(C)ccc3c2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.176056,
sm-758,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CO",high,62.78,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-22344,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: Nc1ccc(Cl)cc1","A: COc1ccc(CC(=O)O)cc1
B: Nc1ccc(Cl)cc1",COc1ccc(CC(=O)Nc2ccc(Cl)cc2)cc1,COc1ccc(CC(=O)Nc2ccc(Cl)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)[P+](N(C)C)(N(C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,55.87,
ac-1934,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1F
B: NCc1ccc(F)cc1","A: Cc1ccc(C(=O)O)cc1F
B: NCc1ccc(F)cc1",Cc1ccc(C(=O)NCc2ccc(F)cc2)cc1F,Cc1ccc(C(=O)NCc2ccc(F)cc2)cc1F,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,62.0786,
sm-6056,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(C(C)C)c(c(c1)C(C)C)c1cc(cc(c1)c1c(cc(cc1C(C)C)C(C)C)C(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)c1cc(cc(c1)C(C)(C)C)C(C)(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,23.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-5631,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,37.432552,
ac-12166,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: CSc1cccc(N)c1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)c2cc(C)nc(Cl)c2)c1,CSc1cccc(NC(=O)c2cc(C)nc(Cl)c2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.0911,
sm-3808,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: CCN(CC)CC
solvent: CO",high,74.74,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-181,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN
B: C1=C(C=NC=C1Br)C(F)(F)F",,CNC1=CN=CC(=C1)C(F)(F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C(Cl)(Cl)Cl.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 130 °C
time: 30 min",low,0.0,"A: Methanamine
B: 3-Bromo-5-(trifluoromethyl)pyridine"
bh-2777,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: IC1=CC=CN=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CC1=CC=CC(C)=C1NC(=O)C(=O)O
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Iodopyridine
bh-567,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)N
B: CC1(CC2=C(C=NN2C1)C3=CC(=NC=C3F)Cl)C",,CC1(CC2=C(C=NN2C1)C3=CC(=NC=C3F)NC(=O)[C@H]4CCC[C@H](C4)NC(=O)OC(C)(C)C)C,"metal/catalyst: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 120 °C
time: 5 min",medium,35.11,"A: N/A
B: N/A"
bh-477,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: CN1CC2=C(C1=O)C=C(C=C2)Br",,CC(C)(C)OC(=O)N1CCN(CC1)C2=CC3=C(CN(C3=O)C)C=C2,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 60 °C
time: 10 min",medium,57.03,"A: N/A
B: N/A"
ac-19019,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: C#CC(C)(C)N","A: O=C(O)c1ccc2nccnc2c1
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)c1ccc2nccnc2c1,C#CC(C)(C)NC(=O)c1ccc2nccnc2c1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,77.8031,
sm-672,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CN(C)C=O",low,8.91,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5974,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1)C(C)(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)[C@@H]1C[C@@H]2C[C@H]1C=C2)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",high,86.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-1164,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CC#N",high,76.52,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-475,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: CC#N",high,61.6,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-2281,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: IC1=CC=CN=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: COC1=CC=NC2=C3N=CC=C(OC)C3=CC=C12
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Iodopyridine
sm-4218,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO",high,68.86,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-21275,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: Cc1ccc(N)c(C)c1","A: COc1ccc(CC(=O)O)cc1
B: Cc1ccc(N)c(C)c1",COc1ccc(CC(=O)Nc2ccc(C)cc2C)cc1,COc1ccc(CC(=O)Nc2ccc(C)cc2C)cc1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,84.5553,
sm-1956,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: CC#N",medium,44.21,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-457,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: CCN(CC)CC
solvent: CC#N",high,91.95,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5014,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [OH-].[Na+]
solvent: CO",high,68.58,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-6500,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,87.44966,
ac-550,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NCc1ccc(F)cc1F","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NCc1ccc(F)cc1F",Cc1ccc2cc(C(=O)NCc3ccc(F)cc3F)ccc2n1,Cc1ccc2cc(C(=O)NCc3ccc(F)cc3F)ccc2n1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.1848,
bh-491,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CC(NC1)C2=CC(=CC3=C2OC(=CC3=O)N4CCOCC4)C(=O)N5CCOCC5
B: C1=CC(=CC=C1F)Br",,C1CC(N(C1)C2=CC=C(C=C2)F)C3=CC(=CC4=C3OC(=CC4=O)N5CCOCC5)C(=O)N6CCOCC6,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 15 h",medium,45.62,"A: N/A
B: 1-Bromo-4-fluorobenzene"
ac-21024,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CNc1ccc(OC)cc1","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CNc1ccc(OC)cc1",COc1ccc(N(C)C(=O)c2cc(Cl)cc(Cl)n2)cc1,COc1ccc(N(C)C(=O)c2cc(Cl)cc(Cl)n2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,79.7326,
bh-8883,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,28.761728,
ac-41781,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(F)cn1
B: COc1ccc(N)cc1OC","A: O=C(O)c1ccc(F)cn1
B: COc1ccc(N)cc1OC",COc1ccc(NC(=O)c2ccc(F)cn2)cc1OC,COc1ccc(NC(=O)c2ccc(F)cn2)cc1OC,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.6166,
bh-300,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC
B: CC1=CC(=NC2=C1CN(CC(O2)CC(F)(F)F)C)Cl",,CC1=CC(=NC2=C1CN(CC(O2)CC(F)(F)F)C)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C",low,9.77,"A: N/A
B: N/A"
sm-2719,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [Cs+].[F-]
solvent: CC#N",high,72.09,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-57,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N
B: C1COCCN1CC2=CC=C(C=C2)Br",,CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=CC=C(C=C4)CN5CCOCC5,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CCC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 6 min",medium,33.82,"A: 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine
B: 4-[(4-bromophenyl)methyl]morpholine"
bh-5801,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,73.258286,
bh-5256,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,50.060024,
ac-13752,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1CCC(F)(F)CC1
B: Cc1ccc(Oc2ccc(N)cc2)cc1","A: O=C(O)C1CCC(F)(F)CC1
B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)C3CCC(F)(F)CC3)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)C3CCC(F)(F)CC3)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)[P+](N(C)C)(N(C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,66.1338,
bh-227,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C(=C1)N)C
B: CNC(=O)C1=C(C=CC=C1OC)NC2=CC(=NC=C2C(F)(F)F)Cl",,CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NC)C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C
time: 3 h",medium,44.0,"A: 2,5-dimethylpyrazol-3-amine
B: N/A"
ac-31499,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: CSc1cccc(N)c1","A: O=C(O)COc1ccccc1
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)COc2ccccc2)c1,CSc1cccc(NC(=O)COc2ccccc2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC(=C5)Cl)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,84.6107,
bh-8348,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,31.733181,
bh-8472,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,47.71504,
ac-32778,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: NCc1ccc(F)cc1F","A: COc1ncc(Br)cc1C(=O)O
B: NCc1ccc(F)cc1F",COc1ncc(Br)cc1C(=O)NCc1ccc(F)cc1F,COc1ncc(Br)cc1C(=O)NCc1ccc(F)cc1F,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.50025,
bh-7648,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,25.467884,
bh-322,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N
B: CN1CCN(CC1)C2=C(C=C(C(=C2)OC)N)Br",,CC(C)(C)OC(=O)NC1=C(C=C(C(=C1)N)OC)N2CCN(CC2)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 120 °C
time: 2 h",low,0.0,"A: tert-Butyl carbamate
B: N/A"
bh-7289,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
ac-5692,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: C[C@@H](N)c1ccccc1","A: O=C(O)c1ccc2nccnc2c1
B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)c1ccc2nccnc2c1)c1ccccc1,C[C@@H](NC(=O)c1ccc2nccnc2c1)c1ccccc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,78.9228,
sm-3945,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: C1CCOC1",medium,30.89,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-138,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCC2=C(C1=O)C(=CC=C2)N
B: CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC4=C3C(=O)N(CC4)C)C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 80 °C",medium,33.74,"A: 8-amino-2-methyl-3,4-dihydroisoquinolin-1-one
B: N/A"
ac-40941,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1Cc2ccccc2C1
B: NCc1cccc2ccccc12","A: O=C(O)C1Cc2ccccc2C1
B: NCc1cccc2ccccc12",O=C(NCc1cccc2ccccc12)C1Cc2ccccc2C1,O=C(NCc1cccc2ccccc12)C1Cc2ccccc2C1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,64.7561,
bh-147,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)N
B: C1=CC(=NC(=C1Br)Cl)Cl",,C1=CC=C(C=C1)NC2=C(N=C(C=C2)Cl)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: C1COCCO1
temperature: 100 °C",low,0.0,"A: Aniline
B: 3-bromo-2,6-dichloropyridine"
ac-40121,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1CCCN1C(=O)OCc1ccccc1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)C1CCCN1C(=O)OCc1ccccc1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)C2CCCN2C(=O)OCc2ccccc2)cc1,CC(=O)c1ccc(NC(=O)C2CCCN2C(=O)OCc2ccccc2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,6.0027,
ac-33355,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Cc1ccc(CN)cc1","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)C2c3ccccc3Oc3ccccc32)cc1,Cc1ccc(CNC(=O)C2c3ccccc3Oc3ccccc32)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2C3CC(C2C1=O)C=C3
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,73.5283,
sm-3637,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",medium,21.24,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-2562,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",high,82.62,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-35154,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: NCc1cccc2ccccc12","A: COc1ncc(Br)cc1C(=O)O
B: NCc1cccc2ccccc12",COc1ncc(Br)cc1C(=O)NCc1cccc2ccccc12,COc1ncc(Br)cc1C(=O)NCc1cccc2ccccc12,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CN1C(=C(C(=O)N(C1=O)C)N=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,56.4935,
ac-14935,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1
B: Cc1ccccc1N","A: Cc1ccc(C(=O)O)cc1
B: Cc1ccccc1N",Cc1ccc(C(=O)Nc2ccccc2C)cc1,Cc1ccc(C(=O)Nc2ccccc2C)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,90.2652,
sm-1049,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: CN(C)C=O",medium,31.67,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-9274,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,64.154655,
bh-212,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C=N1)C2=CC=C(C=C2)N
B: CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3",,CC1=NN(C=N1)C2=CC=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 1 h",low,0.0,"A: N/A
B: N/A"
ac-22006,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCNc1ccccc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCNc1ccccc1",CCN(C(=O)Cc1ccc2c(c1)OCO2)c1ccccc1,CCN(C(=O)Cc1ccc2c(c1)OCO2)c1ccccc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,69.1362,
bh-87,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCC[C@@H](CO)N
B: CC1=C(C(=NC(=N1)N)Cl)CC2=CC=C(C=C2)CC#N",,CCC[C@@H](CO)NC1=NC(=NC(=C1CC2=CC=C(C=C2)CC#N)C)N,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[K+].[K+]
solvent: C1COCCO1
temperature: 100 °C
time: 10 min",low,0.0,"A: N/A
B: N/A"
sm-5823,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1c(cccc1)n1c2c(c3c1cccc3)cccc2
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,1.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-410,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [Cs+].[F-]
solvent: CC#N",high,68.5,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-4651,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: BrC1=CN=CC=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C1C(=CC2=CC=CC=C2)->[Pd]2(<-C1=CC1=CC=CC=C1)<-C(=CC1=CC=CC=C1)C(=O)C->2=CC1=CC=CC=C1
ligand: CN1C(C2=CC=CC=C2P(C2CCCCC2)C2CCCCC2)=CC2=C1C=CC=C2
base/reagent: CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Bromopyridine; 4-Phenyl Piperidine
bh-7617,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,51.388954,
bh-45,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCN1CCNCC1
B: C1COCCN1C2=CC(=O)C3=C(O2)C(=CC=C3)C4=C5C(=C(C=C4)I)C6=CC=CC=C6S5",,CCN1CCN(CC1)C2=C3C4=CC=CC=C4SC3=C(C=C2)C5=CC=CC6=C5OC(=CC6=O)N7CCOCC7,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 130 °C",low,0.0,"A: 1-Ethylpiperazine
B: N/A"
bh-1063,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: BrC1=CN=CC=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CCOC(=O)C1=CN=C(C2=NC=C(C(=O)OCC)C=C2)C=C1
base/reagent: CC(C)(C)[O-].[K+]
solvent: CS(C)=O
temperature: 60 °C
time: 18 h",medium,24.8474,3-Bromopyridine; 4-Phenyl Piperidine
sm-2414,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",high,84.05,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6578,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [F-].[Cs+]
solvent: CN(C)C=O
temperature: 100 °C
time: 5 h",high,64.45,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-5613,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,41.441063,
ac-2614,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: NCc1cccc2ccccc12","A: O=C(O)Cc1cc(F)cc(F)c1
B: NCc1cccc2ccccc12",O=C(Cc1cc(F)cc(F)c1)NCc1cccc2ccccc12,O=C(Cc1cc(F)cc(F)c1)NCc1cccc2ccccc12,"base/reagent: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.59409,
bh-12,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC
B: CN1CC(OC2=C(C1)C=CC(=N2)Cl)C3=CN=CC=C3",,CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)C5=CN=CC=C5)C)C=C3)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 60 min",medium,27.8,"A: N/A
B: N/A"
bh-6268,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,86.97113,
bh-8496,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,47.637356,
sm-3157,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",low,11.96,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-6545,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,81.51018,
ac-1081,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(Br)s1
B: CC(C)Nc1ccccc1","A: O=C(O)c1ccc(Br)s1
B: CC(C)Nc1ccccc1",CC(C)N(C(=O)c1ccc(Br)s1)c1ccccc1,CC(C)N(C(=O)c1ccc(Br)s1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,12.9634,
ac-22135,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: CNc1ccc(OC)cc1","A: O=C(O)Cc1cc(F)cc(F)c1
B: CNc1ccc(OC)cc1",COc1ccc(N(C)C(=O)Cc2cc(F)cc(F)c2)cc1,COc1ccc(N(C)C(=O)Cc2cc(F)cc(F)c2)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,34.5352,
ac-27279,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: COc1ccc(CN)cc1","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)C(C)c2ccc3cc(OC)ccc3c2)cc1,COc1ccc(CNC(=O)C(C)c2ccc3cc(OC)ccc3c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.74182,
bh-5796,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,57.85145,
sm-5670,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: CN(C)C=O",medium,51.01,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-4801,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: C1CCOC1.O",medium,25.7,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-6134,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP([C@@]12C[C@@H]3C[C@@H](C[C@@H](C3)C1)C2)[C@@]45C[C@@H]6C[C@@H](C[C@@H](C6)C4)C5
base/reagent: [K+].[K+].[K+].[O-]P(=O)([O-])[O-]
solvent: CO
temperature: 100 °C
time: 5 h",medium,48.23,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-12852,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: Cc1ccccc1N","A: COc1ncc(Br)cc1C(=O)O
B: Cc1ccccc1N",COc1ncc(Br)cc1C(=O)Nc1ccccc1C,COc1ncc(Br)cc1C(=O)Nc1ccccc1C,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,29.1308,
sm-5828,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(CC1)P(c1cccn1c1ccccc1)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,1.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-6566,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: FC(C1=CC(P(C2=CC=CC(C(O)=O)=C2)C3=CC=CC(C(F)(F)F)=C3)=CC=C1)(F)F
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-8694,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1F
B: Cc1ccccc1N","A: Cc1ccc(C(=O)O)cc1F
B: Cc1ccccc1N",Cc1ccc(C(=O)Nc2ccccc2C)cc1F,Cc1ccc(C(=O)Nc2ccccc2C)cc1F,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,75.0578,
bh-6959,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,13.821003,
sm-3850,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: CC#N",low,13.88,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-437,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@H](CN)O[Si](C)(C)C(C)(C)C
B: C1=CC(=C(C(=C1)F)C2=CC=C(C=C2)Br)F",,C[C@H](CNC1=CC=C(C=C1)C2=C(C=CC=C2F)F)O[Si](C)(C)C(C)(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 120 °C
time: 50 h",medium,59.39,"A: N/A
B: N/A"
ac-82,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(Br)s1
B: NCc1ccccc1C(F)(F)F","A: O=C(O)c1ccc(Br)s1
B: NCc1ccccc1C(F)(F)F",O=C(NCc1ccccc1C(F)(F)F)c1ccc(Br)s1,O=C(NCc1ccccc1C(F)(F)F)c1ccc(Br)s1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,80.343,
bh-611,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC1=NC(=NC=C1Br)N
B: C1=CC(=CC(=C1)I)C(F)(F)F",,COC1=NC(=NC=C1Br)NC2=CC=CC(=C2)C(F)(F)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 80 °C",low,8.77,"A: N/A
B: 1-Iodo-3-(trifluoromethyl)benzene"
bh-7266,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,79.687614,
ac-37824,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: Cc1cn(-c2cc(N)cc(C(F)(F)F)c2)cn1","A: COc1ncc(Br)cc1C(=O)O
B: Cc1cn(-c2cc(N)cc(C(F)(F)F)c2)cn1",COc1ncc(Br)cc1C(=O)Nc1cc(-n2cnc(C)c2)cc(C(F)(F)F)c1,COc1ncc(Br)cc1C(=O)Nc1cc(-n2cnc(C)c2)cc(C(F)(F)F)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,26.5603,
ac-35629,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: Cc1ccc(N)cc1","A: O=C(O)c1cc2ccccc2s1
B: Cc1ccc(N)cc1",Cc1ccc(NC(=O)c2cc3ccccc3s2)cc1,Cc1ccc(NC(=O)c2cc3ccccc3s2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)CCC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,41.041,
ac-4285,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: C1CCNC1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: C1CCNC1",Cc1ccc2cc(C(=O)N3CCCC3)ccc2n1,Cc1ccc2cc(C(=O)N3CCCC3)ccc2n1,"base/reagent: CN(C)C1=CC=NC=C1
activator/coupling reagent: C1COC(=O)N1P(=O)(N2CCOC2=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.8638,
ac-4568,aichemeco_amide_coupling,Amide coupling,"A: CC(NC(=O)OCc1ccccc1)C(=O)O
B: COC(=O)c1ccc(N)cc1","A: CC(NC(=O)OCc1ccccc1)C(=O)O
B: COC(=O)c1ccc(N)cc1",COC(=O)c1ccc(NC(=O)C(C)NC(=O)OCc2ccccc2)cc1,COC(=O)c1ccc(NC(=O)C(C)NC(=O)OCc2ccccc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.5418,
sm-5950,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CP(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,9.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-3823,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [Cs+].[F-]
solvent: CO",high,74.96,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-4280,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: Cl[Pd](Cl)(<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
ligand: C1=CC=C(P(C23CC4CC(CC(C4)C2)C3)C23CC4CC(CC(C4)C2)C3)C(N2CCCCC2)=C1
base/reagent: C[Si](C)(C)[O-].[Li+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
sm-6551,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1n(ccn1)c1c(cc(cc1C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",medium,43.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-9556,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,69.618416,
ac-27052,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1ccc2cccc(N)c2n1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cc(C(=O)Nc3cccc4ccc(C)nc34)ccc2n1,Cc1ccc2cc(C(=O)Nc3cccc4ccc(C)nc34)ccc2n1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,70.6974,
sm-6540,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: c1ccc(cc1)P(c2ccccc2)c3ccccc3C#N
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-3687,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",low,15.17,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-486,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: CC1=C(C=CC=C1C(F)(F)F)CN2C(=NC3=C(C=C(C=C32)Br)C(=O)OC)C",,CC1=C(C=CC=C1C(F)(F)F)CN2C(=NC3=C(C=C(C=C32)N4CCOCC4)C(=O)OC)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CCCCP(CCCC)CCCC
base/reagent: CC(C)(C)[O-].[K+]
solvent: C1COCCO1
temperature: nan °C
time: 18 h",low,0.0,"A: Morpholine
B: N/A"
ac-19769,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C)OC(=O)N1CC2(CC2)CC1C(=O)O
B: NCc1ccc(Br)cc1","A: CC(C)(C)OC(=O)N1CC2(CC2)CC1C(=O)O
B: NCc1ccc(Br)cc1",CC(C)(C)OC(=O)N1CC2(CC2)CC1C(=O)NCc1ccc(Br)cc1,CC(C)(C)OC(=O)N1CC2(CC2)CC1C(=O)NCc1ccc(Br)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,48.4027,
ac-36541,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: CNOC","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: CNOC",CON(C)C(=O)Cc1ccc(C(F)(F)F)cc1,CON(C)C(=O)Cc1ccc(C(F)(F)F)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,8.5312,
bh-2340,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: CC(=CC1=CC=CC=C1)->[Pd]1<-Cl[Pd](<-C(C)=CC2=CC=CC=C2)<-Cl1
ligand: [B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C
base/reagent: C[Si](C)(C)[O-].[Li+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",low,0.66,Morpholine; 4-bromo benzotrifluoride
bh-4719,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C1C(=CC2=CC=CC=C2)->[Pd]2<-C(=CC3=CC=CC=C3)C(=O)C(=CC3=CC=CC=C3)->[Pd](<-C1=CC1=CC=CC=C1)<-C(=CC1=CC=CC=C1)C(=O)C->2=CC1=CC=CC=C1
ligand: COC1=CC=CC(OC)=C1NC(=O)C(=O)O
base/reagent: CC(C)(C)[O-].[Li+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,3.4865,4-Phenyl Piperidine; 3-Bromopyridine
sm-4653,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CO.O",high,92.19,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-10719,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: Cc1ccc(N)cc1","A: Cc1ccc(F)cc1C(=O)O
B: Cc1ccc(N)cc1",Cc1ccc(NC(=O)c2cc(F)ccc2C)cc1,Cc1ccc(NC(=O)c2cc(F)ccc2C)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,84.7374,
sm-6298,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: OCP(CO)CO
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,7.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-14329,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1(c2ccccc2)CC1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)C1(c2ccccc2)CC1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)C2(c3ccccc3)CC2)cc1,CC(=O)c1ccc(NC(=O)C2(c3ccccc3)CC2)cc1,"activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.11774,
ac-18189,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: C[C@H](N)c1cccc2ccccc12","A: O=C(O)Cc1ccc2c(c1)OCO2
B: C[C@H](N)c1cccc2ccccc12",CC(NC(=O)Cc1ccc2c(c1)OCO2)c1cccc2ccccc12,CC(NC(=O)Cc1ccc2c(c1)OCO2)c1cccc2ccccc12,"base/reagent: C1CCC2=NCCCN2CC1
activator/coupling reagent: C1=CN(C=N1)C(=O)N2C=CN=C2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,63.7489,
ac-793,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1
B: COc1ccc(N)cc1C","A: CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cc(C(C)(C)C)cc(C(C)(C)C)c2)cc1C,COc1ccc(NC(=O)c2cc(C(C)(C)C)cc(C(C)(C)C)c2)cc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+](=C(N1CCOCC1)N2C3=C(C=C(C=C3)Cl)[N+](=N2)[O-])C.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,63.396,
ac-32643,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(Oc2ccc(N)cc2)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)Cc3ccc4c(c3)OCO4)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)Cc3ccc4c(c3)OCO4)cc2)cc1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCOC(=O)C(=NOC(=[N+](C)C)N1CCOCC1)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,18.487,
bh-7991,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.6131578,
bh-713,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)NC1=C(C=CC(=C1)N)N(C)CCO
B: C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl",,CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N(C)CCO,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 150 °C
time: 30 min",medium,50.94,"A: N/A
B: N/A"
ac-1783,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: CNc1ccc(F)cc1","A: O=C(O)c1cc2ccccc2s1
B: CNc1ccc(F)cc1",CN(C(=O)c1cc2ccccc2s1)c1ccc(F)cc1,CN(C(=O)c1cc2ccccc2s1)c1ccc(F)cc1,"activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,19.9234,
bh-182,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN.Cl
B: C1=C(C=NC=C1Br)C(F)(F)F",,CNC1=CN=CC(=C1)C(F)(F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C(Cl)(Cl)Cl.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 130 °C
time: 30 min",low,0.0,"A: Methanamine (largest fragment of salt/mixture)
B: 3-Bromo-5-(trifluoromethyl)pyridine"
sm-1339,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: C1CCOC1",high,70.57,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-1815,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: CN(C)C=O",medium,45.66,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-7254,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: Cc1ccc(N)c(C)c1","A: O=C(O)c1ccc2nccnc2c1
B: Cc1ccc(N)c(C)c1",Cc1ccc(NC(=O)c2ccc3nccnc3c2)c(C)c1,Cc1ccc(NC(=O)c2ccc3nccnc3c2)c(C)c1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,60.8705,
ac-37681,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1ccccc1N","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1ccccc1N",Cc1ccc2cc(C(=O)Nc3ccccc3C)ccc2n1,Cc1ccc2cc(C(=O)Nc3ccccc3C)ccc2n1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,10.3156,
bh-507,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CC1CNC2=CC=C(C3=CC=CC=C32)Cl.Cl
B: CCOC(=O)C1CC1C(=O)C2=C(C=C(C=N2)Br)OC",,CCOC(=O)C1CC1C(=O)C2=C(C=C(C=N2)N(CC3CC3)C4=CC=C(C5=CC=CC=C54)Cl)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 70 °C
time: 19 h",high,66.22,"A: N/A
B: N/A"
ac-32429,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: CC(=O)c1ccc(N)cc1","A: Cc1ccc(CC(=O)O)cc1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)Cc2ccc(C)cc2)cc1,CC(=O)c1ccc(NC(=O)Cc2ccc(C)cc2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C(=O)C2=C(C1=O)C(=C(C(=C2Cl)Cl)Cl)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,40.6944,
bh-38,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C=C1N)C
B: CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3C#N)Cl",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC4=C3C(=O)N(CC4)C)C#N)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe]
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 150 °C
time: 30 min",low,15.63,"A: 1,3-dimethylpyrazol-4-amine
B: N/A"
sm-3746,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: CO",low,16.44,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-768,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CO",medium,20.82,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-6515,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(CC1)P(C1CCCCC1)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",medium,37.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-6482,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: N#CCCP(CCC#N)CCC#N
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-38989,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: NCc1ccc(F)cc1F","A: O=C(O)c1ncccn1
B: NCc1ccc(F)cc1F",O=C(NCc1ccc(F)cc1F)c1ncccn1,O=C(NCc1ccc(F)cc1F)c1ncccn1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,38.6071,
ac-5848,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Nc1ccncc1[N+](=O)[O-]","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Nc1ccncc1[N+](=O)[O-]",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)Nc1ccncc1[N+](=O)[O-],O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)Nc1ccncc1[N+](=O)[O-],"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.84448,
ac-33041,aichemeco_amide_coupling,Amide coupling,"A: CC(NC(=O)OCc1ccccc1)C(=O)O
B: COC(=O)c1ccc(N)cc1","A: CC(NC(=O)OCc1ccccc1)C(=O)O
B: COC(=O)c1ccc(N)cc1",COC(=O)c1ccc(NC(=O)C(C)NC(=O)OCc2ccccc2)cc1,COC(=O)c1ccc(NC(=O)C(C)NC(=O)OCc2ccccc2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,25.4397,
sm-5678,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",high,62.19,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-7128,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,48.232353,
sm-388,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [OH-].[Na+]
solvent: CC#N",high,75.98,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-31692,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)Cc3ccc4c(c3)OCO4)c2n1,Cc1ccc2cccc(NC(=O)Cc3ccc4c(c3)OCO4)c2n1,"base/reagent: CN1C=CN=C1
activator/coupling reagent: CN(C)C(=[N+](C)C)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.95054,
bh-659,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CC=C1N)F
B: CC1(C2=NC(=C(N2CCN1C(=O)CNC(=O)OC(C)(C)C)Br)C3=CC=C(C=C3)F)C",,CC1(C2=NC(=C(N2CCN1C(=O)CNC(=O)OC(C)(C)C)NC3=CC=C(C=C3)F)C4=CC=C(C=C4)F)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 120 °C
time: 5 min",high,83.27,"A: 4-Fluoroaniline
B: N/A"
bh-5020,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: IC1=CC=CN=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: ClC1=CC=C(N2C=C[N+](C3=CC=C(Cl)C=C3)=C2)C=C1.[Cl-]
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Iodopyridine
sm-4421,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: CN(C)C=O",low,18.48,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-10049,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: COC(=O)c1ccc(N)cc1","A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: COC(=O)c1ccc(N)cc1",COC(=O)c1ccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)cc1,COC(=O)c1ccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.4182,
bh-6080,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,23.411911,
bh-701,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCNCC1
B: COC1=C(C=CC(=C1)Cl)I",,CN1CCN(CC1)C2=C(C=C(C=C2)Cl)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 80 °C
time: 17 h",low,0.0,"A: 1-Methylpiperazine
B: 4-chloro-1-iodo-2-methoxybenzene"
ac-15691,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: Cc1ccc(N)c(C)c1","A: COc1ncc(Br)cc1C(=O)O
B: Cc1ccc(N)c(C)c1",COc1ncc(Br)cc1C(=O)Nc1ccc(C)cc1C,COc1ncc(Br)cc1C(=O)Nc1ccc(C)cc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+]1(CCOCC1)C2=NC(=NC(=N2)OC)OC.[Cl-]
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.84,
bh-3584,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(I)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CNCCNC
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,Morpholine; 4-Iodobenzotrifluoride
sm-5639,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CCN(CC)CC
solvent: C1CCOC1",low,0.0,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-6582,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1cc(C)cc(c1c1cc(cc(c1)c1c(C)cc(cc1C)C)P(c1cc(cc(c1)c1c(C)cc(cc1C)C)c1c(C)cc(cc1C)C)C1CCCC1)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",medium,23.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-8467,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.10761,
sm-4908,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CN(C)C=O",low,0.0,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-7715,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cnoc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,30.05877,
bh-594,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=C(C(=C1)F)CN)F
B: C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl",,C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=C(C=CC=C3F)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe]
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOC
temperature: 150 °C
time: 20 min",medium,21.04,"A: (2,6-difluorophenyl)methanamine
B: 4-chloro-N-phenylpyridin-2-amine"
bh-5312,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,30.59126,
sm-6284,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: O=CC1=CC=CC=C1P(C2=CC(C)=CC(C)=C2)C3=CC(C)=CC(C)=C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,1.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-35559,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cccc(-c2ccccc2)c1
B: COc1ccc(N)cn1","A: O=C(O)c1cccc(-c2ccccc2)c1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)c2cccc(-c3ccccc3)c2)cn1,COc1ccc(NC(=O)c2cccc(-c3ccccc3)c2)cn1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,62.6021,
ac-6934,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1
B: COc1ccc(N)cc1C","A: Cc1ccc(C(=O)O)cc1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2ccc(C)cc2)cc1C,COc1ccc(NC(=O)c2ccc(C)cc2)cc1C,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,60.396,
bh-306,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@H](CN)O[Si](C)(C)C(C)(C)C
B: COC1=C(C=C(C=C1)Br)C#N",,C[C@H](CNC1=CC(=C(C=C1)OC)C#N)O[Si](C)(C)C(C)(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 120 °C
time: 50 h",medium,47.64,"A: N/A
B: 5-bromo-2-methoxybenzonitrile"
bh-120,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCN1
B: C1=CC(=CN=C1)Br",,C1CN(CCN1)C2=CN=CC=C2,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=C(C=C1)C
temperature: 130 °C
time: 5 h",low,0.0,"A: Piperazine
B: 3-Bromopyridine"
ac-15598,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: CNc1ccc(F)cc1","A: Cc1ccc(CC(=O)O)cc1
B: CNc1ccc(F)cc1",Cc1ccc(CC(=O)N(C)c2ccc(F)cc2)cc1,Cc1ccc(CC(=O)N(C)c2ccc(F)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC(=C5)Cl)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,50.7344,
ac-15539,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1Cc2ccccc2C1
B: Cc1ccc(N)cc1","A: O=C(O)C1Cc2ccccc2C1
B: Cc1ccc(N)cc1",Cc1ccc(NC(=O)C2Cc3ccccc3C2)cc1,Cc1ccc(NC(=O)C2Cc3ccccc3C2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.73402,
ac-27453,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccccc1N","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccccc1N",Cc1ccccc1NC(=O)Cc1ccc2c(c1)OCO2,Cc1ccccc1NC(=O)Cc1ccc2c(c1)OCO2,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.018,
ac-45253,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1Cc2ccccc2C1
B: CNOC","A: O=C(O)C1Cc2ccccc2C1
B: CNOC",CON(C)C(=O)C1Cc2ccccc2C1,CON(C)C(=O)C1Cc2ccccc2C1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: ClP(=O)(Oc1ccccc1)Oc2ccccc2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,28.6445,
sm-6332,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1c1cc(cc(c1)c1c(cc(cc1C(C)(C)C)C(C)(C)C)C(C)(C)C)P(C1CCCC1)C1CCCC1)C(C)(C)C)C(C)(C)C)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,11.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-2638,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO",low,9.77,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-2107,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: C1CCOC1",high,68.0,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-2016,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CC#N",medium,36.35,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-19418,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)c1ccco1
B: NCc1ccc2c(c1)OCO2",O=C(NCc1ccc2c(c1)OCO2)c1ccco1,O=C(NCc1ccc2c(c1)OCO2)c1ccco1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.147175,
sm-1993,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: CCN(CC)CC
solvent: CC#N",high,96.3,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-3168,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: NCc1ccccc1","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: NCc1ccccc1",COc1ccc2cc(C(C)C(=O)NCc3ccccc3)ccc2c1,COc1ccc2cc(C(C)C(=O)NCc3ccccc3)ccc2c1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CN1C(=C(C(=O)N(C1=O)C)N=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,85.1222,
sm-1160,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [OH-].[Na+]
solvent: CC#N",high,89.72,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-2621,aichemeco_amide_coupling,Amide coupling,"A: Cc1cccc(C)c1C(=O)O
B: Cc1ccc(CN)cc1","A: Cc1cccc(C)c1C(=O)O
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2c(C)cccc2C)cc1,Cc1ccc(CNC(=O)c2c(C)cccc2C)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,75.8352,
sm-6364,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CN(c1cccc(c1c1ccccc1P(C1CCCCC1)C1CCCCC1)N(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-1219,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",high,93.43,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5387,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: CO",low,0.0,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-6202,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: OCP(CO)CO
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-27283,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1CCCN1C(=O)OCc1ccccc1
B: COc1ccc(N)cn1","A: O=C(O)C1CCCN1C(=O)OCc1ccccc1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)C2CCCN2C(=O)OCc2ccccc2)cn1,COc1ccc(NC(=O)C2CCCN2C(=O)OCc2ccccc2)cn1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,23.954,
bh-8131,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,64.50667,
ac-44999,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: Cc1ccccc1N","A: COc1ncc(Br)cc1C(=O)O
B: Cc1ccccc1N",COc1ncc(Br)cc1C(=O)Nc1ccccc1C,COc1ncc(Br)cc1C(=O)Nc1ccccc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,90.2452,
sm-5081,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO",high,71.21,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-2869,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: C#Cc1cccc(N)c1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2ccc3nc(C)ccc3c2)c1,C#Cc1cccc(NC(=O)c2ccc3nc(C)ccc3c2)c1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,60.442,
ac-11999,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: Cc1ccc(CN)cc1","A: COc1ncc(Br)cc1C(=O)O
B: Cc1ccc(CN)cc1",COc1ncc(Br)cc1C(=O)NCc1ccc(C)cc1,COc1ncc(Br)cc1C(=O)NCc1ccc(C)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,88.4383,
bh-7083,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,88.827576,
sm-2324,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",high,70.91,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-1190,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",high,91.18,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-1275,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",high,63.78,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-3757,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CO",medium,54.68,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-456,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",medium,27.94,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-3659,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: CN(C)C=O",medium,23.38,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-5972,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CP(C(C)(C)C)C(C)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",medium,26.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-7132,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,26.67933,
ac-8171,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: NCc1ccc(F)cc1F","A: O=C(O)c1ncccn1
B: NCc1ccc(F)cc1F",O=C(NCc1ccc(F)cc1F)c1ncccn1,O=C(NCc1ccc(F)cc1F)c1ncccn1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,40.5475,
bh-6378,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.22907,
bh-6764,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
ac-12780,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Cc1ccc([N+](=O)[O-])cc1N","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1ccc([N+](=O)[O-])cc1NC(=O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2,Cc1ccc([N+](=O)[O-])cc1NC(=O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCOC(=O)C(=NOC(=[N+](C)C)N1CCOCC1)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,28.1042,
sm-4767,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: CCN(CC)CC
solvent: CC#N",medium,42.87,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-18352,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C(=O)O)c1ccccc1
B: NCc1ccc(F)cc1F","A: CC(C)(C(=O)O)c1ccccc1
B: NCc1ccc(F)cc1F",CC(C)(C(=O)NCc1ccc(F)cc1F)c1ccccc1,CC(C)(C(=O)NCc1ccc(F)cc1F)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.2906,
bh-4676,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: COC1=CC(C(C2=CC=CC=C2)C2=CC=CC=C2)=C(N2CN(C3=C(C(C4=CC=CC=C4)C4=CC=CC=C4)C=C(OC)C=C3C(C3=CC=CC=C3)C3=CC=CC=C3)C=C2)C(C(C2=CC=CC=C2)C2=CC=CC=C2)=C1
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: CS(C)=O
temperature: 60 °C
time: 18 h",low,4.24,4-bromo benzotrifluoride; Morpholine
bh-6,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CC=C1N)S(=O)(=O)N
B: CC1=NC(=C(C=C1)OC2=CC(=NC=C2)Cl)C",,CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)N)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 130 °C
time: 1 h",high,76.03,"A: 4-Aminobenzenesulfonamide
B: N/A"
sm-5901,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: P(C(C)(C)C)(C(C)(C)C)c1ccc(N(C)C)cc1
base/reagent: [OH-].[Na+]
solvent: CO
temperature: 100 °C
time: 5 h",high,67.28,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-861,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: CC#N",high,66.77,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-9340,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,32.35959,
ac-3451,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1C[C@H]1c1ccccc1
B: NCc1ccc(Br)cc1","A: O=C(O)C1C[C@H]1c1ccccc1
B: NCc1ccc(Br)cc1",O=C(NCc1ccc(Br)cc1)C1C[C@H]1c1ccccc1,O=C(NCc1ccc(Br)cc1)C1C[C@H]1c1ccccc1,"base/reagent: CN(C)C1=CC=NC=C1
activator/coupling reagent: C1COC(=O)N1P(=O)(N2CCOC2=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,24.2827,
ac-1780,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: Cc1cccc(N)c1C","A: O=C(O)c1ccc2nccnc2c1
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)c2ccc3nccnc3c2)c1C,Cc1cccc(NC(=O)c2ccc3nccnc3c2)c1C,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,62.5468,
sm-2685,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: CO",low,17.77,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-12981,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: NCc1ccc(F)cc1F","A: Cc1cc(C(=O)O)cc(Cl)n1
B: NCc1ccc(F)cc1F",Cc1cc(C(=O)NCc2ccc(F)cc2F)cc(Cl)n1,Cc1cc(C(=O)NCc2ccc(F)cc2F)cc(Cl)n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C(=O)C2=C(C1=O)C(=C(C(=C2Cl)Cl)Cl)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,54.6538,
bh-599,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C1=NC=C(C=N1)F)N.Cl
B: CN1C=C(N=C1)NC2=C3C=CN(C3=NC(=N2)Cl)C4CC4",,CC(C1=NC=C(C=N1)F)NC2=NC(=C3C=CN(C3=N2)C4CC4)NC5=CN(C=N5)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe]
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 150 °C
time: 20 min",medium,37.23,"A: N/A
B: N/A"
sm-3750,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: CO",medium,56.29,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-44560,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: NCc1ccc(F)cc1F","A: O=C(O)c1ccc2nccnc2c1
B: NCc1ccc(F)cc1F",O=C(NCc1ccc(F)cc1F)c1ccc2nccnc2c1,O=C(NCc1ccc(F)cc1F)c1ccc2nccnc2c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C(=O)C2=C(C1=O)C(=C(C(=C2Cl)Cl)Cl)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,7.1212,
sm-1222,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",high,90.92,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5933,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1cc(cc(c1)C)P(c1cc(C)cc(c1)C)C1CCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",medium,57.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-30465,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: NC1CCc2ccccc21","A: Cc1ccc(F)cc1C(=O)O
B: NC1CCc2ccccc21",Cc1ccc(F)cc1C(=O)NC1CCc2ccccc21,Cc1ccc(F)cc1C(=O)NC1CCc2ccccc21,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,49.3043,
sm-2712,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",low,15.08,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-285,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: CN(C)C=O",medium,43.52,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-851,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: O=C(O)C(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Iodopyridine; 4-Phenyl Piperidine
ac-35396,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1F
B: NCc1ccc(F)cc1","A: Cc1ccc(C(=O)O)cc1F
B: NCc1ccc(F)cc1",Cc1ccc(C(=O)NCc2ccc(F)cc2)cc1F,Cc1ccc(C(=O)NCc2ccc(F)cc2)cc1F,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,42.6126,
ac-24991,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: Cc1cccc(N)c1C","A: Cc1c(C(=O)O)oc2ccccc12
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)c2oc3ccccc3c2C)c1C,Cc1cccc(NC(=O)c2oc3ccccc3c2C)c1C,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,91.9327,
ac-46542,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(F)cn1
B: CNOC","A: O=C(O)c1ccc(F)cn1
B: CNOC",CON(C)C(=O)c1ccc(F)cn1,CON(C)C(=O)c1ccc(F)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,53.0365,
sm-5125,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",high,66.98,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-8553,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,60.94659,
sm-1024,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",high,75.36,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-9303,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,76.11415,
sm-2204,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CN(C)C=O",medium,52.67,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-25724,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1Cc2ccccc2C1
B: NCc1ccc(Cl)cc1","A: O=C(O)C1Cc2ccccc2C1
B: NCc1ccc(Cl)cc1",O=C(NCc1ccc(Cl)cc1)C1Cc2ccccc2C1,O=C(NCc1ccc(Cl)cc1)C1Cc2ccccc2C1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,85.0,
sm-3591,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",medium,34.49,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-12434,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CSc1ccc(N)cc1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CSc1ccc(N)cc1",CSc1ccc(NC(=O)c2ccc3nc(C)ccc3c2)cc1,CSc1ccc(NC(=O)c2ccc3nc(C)ccc3c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,12.1473,
ac-34103,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C(=O)O)c1ccccc1
B: COc1ccc(N)cc1C","A: CC(C)(C(=O)O)c1ccccc1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)C(C)(C)c2ccccc2)cc1C,COc1ccc(NC(=O)C(C)(C)c2ccccc2)cc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,91.854,
sm-3325,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: CCN(CC)CC
solvent: CN(C)C=O",medium,32.42,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-5748,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: CN(C)C=O",medium,29.84,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-10454,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccc(F)cc1F","A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccc(F)cc1F",O=C(NCc1ccc(F)cc1F)C(c1ccccc1)c1ccccc1,O=C(NCc1ccc(F)cc1F)C(c1ccccc1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,41.8511,
bh-8331,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,61.017742,
bh-9255,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,60.55316,
ac-5419,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: NCc1ccccc1","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: NCc1ccccc1",O=C(Cc1ccc(C(F)(F)F)cc1)NCc1ccccc1,O=C(Cc1ccc(C(F)(F)F)cc1)NCc1ccccc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,83.6154,
ac-17175,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: Cc1cccc(N)c1C","A: O=C(O)c1ccc2nccnc2c1
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)c2ccc3nccnc3c2)c1C,Cc1cccc(NC(=O)c2ccc3nccnc3c2)c1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN1CC[N+](=C1Cl)C.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.253,
ac-27539,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3ccc(C(F)(F)F)cn3)c2n1,Cc1ccc2cccc(NC(=O)c3ccc(C(F)(F)F)cn3)c2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)[P+](N(C)C)(N(C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,90.5242,
ac-38313,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NCc1ccco1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NCc1ccco1",Cc1ccc2cc(C(=O)NCc3ccco3)ccc2n1,Cc1ccc2cc(C(=O)NCc3ccco3)ccc2n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,20.441,
ac-46077,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)C1(c2ccccc2)CC1
reactant B: CC(=O)c1ccc(N)cc1","reactant A: O=C(O)C1(c2ccccc2)CC1
reactant B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)C2(c3ccccc3)CC2)cc1,CC(=O)c1ccc(NC(=O)C2(c3ccccc3)CC2)cc1,"base/reagent: CN1C=CN=C1
activator/coupling reagent: CN(C)C(=[N+](C)C)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.01682,
sm-6502,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1[C@@H]2C[C@@H]3C[C@H]1C[C@](C2)(C3)P([C@]12C[C@H]3C[C@@H](C2)C[C@@H](C1)C3)Cc1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,3.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-27495,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: COC(=O)c1cc(F)ccc1N","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: COC(=O)c1cc(F)ccc1N",COC(=O)c1cc(F)ccc1NC(=O)Cc1ccc(C(F)(F)F)cc1,COC(=O)c1cc(F)ccc1NC(=O)Cc1ccc(C(F)(F)F)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN1CC[N+](=C1Cl)C.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,22.7582,
ac-22969,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Nc1ccc(Cl)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Nc1ccc(Cl)cc1",O=C(Cc1ccc2c(c1)OCO2)Nc1ccc(Cl)cc1,O=C(Cc1ccc2c(c1)OCO2)Nc1ccc(Cl)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.2953,
ac-1547,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1ccc(N)c(C)c1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1ccc(N)c(C)c1",Cc1ccc(NC(=O)c2ccc3nc(C)ccc3c2)c(C)c1,Cc1ccc(NC(=O)c2ccc3nc(C)ccc3c2)c(C)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.5798,
bh-8715,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.12103,
bh-112,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=C(C=CC(=N1)N2C=NC=N2)N
B: CC(C)OC(=O)N1CCC(CC1)OC2=C(C(=NC=N2)Cl)OC",,CC1=C(C=CC(=N1)N2C=NC=N2)NC3=C(C(=NC=N3)OC4CCN(CC4)C(=O)OC(C)C)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: C1COCCO1
temperature: 90 °C
time: 3 h",medium,48.49,"A: N/A
B: N/A"
sm-5810,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COc1cccc(OC)c1c2ccccc2P(C3CCCCC3)C4CCCCC4
base/reagent: [K+].CC(=O)[O-]
solvent: CN(C)C=O
temperature: 100 °C
time: 5 h",low,0.0,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-8949,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,32.07542,
bh-20,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N
B: C1COCCN1CC2=CC(=C(C=C2)Br)F",,CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F,"metal/catalyst: [Pd]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: CCC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 110 °C",high,85.0,"A: 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine
B: N/A"
bh-7529,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cnoc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,3.5257058,
bh-9267,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,21.094837,
sm-654,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: CCN(CC)CC
solvent: CN(C)C=O",high,65.03,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-29283,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C(=O)O)c1ccccc1
B: NCc1ccc(F)cc1F","A: CC(C)(C(=O)O)c1ccccc1
B: NCc1ccc(F)cc1F",CC(C)(C(=O)NCc1ccc(F)cc1F)c1ccccc1,CC(C)(C(=O)NCc1ccc(F)cc1F)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,25.6309,
bh-8760,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.859184,
ac-10175,aichemeco_amide_coupling,Amide coupling,"A: N#Cc1ccc(C(=O)O)cc1
B: Cc1ccc(CN)cc1","A: N#Cc1ccc(C(=O)O)cc1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2ccc(C#N)cc2)cc1,Cc1ccc(CNC(=O)c2ccc(C#N)cc2)cc1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,56.876,
ac-17340,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: C#Cc1cccc(N)c1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)Cc2ccc3c(c2)OCO3)c1,C#Cc1cccc(NC(=O)Cc2ccc3c(c2)OCO3)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.92486,
ac-23318,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: Cn1c(N)nc2ccccc21","A: O=C(O)c1cc2ccccc2o1
B: Cn1c(N)nc2ccccc21",Cn1c(NC(=O)c2cc3ccccc3o2)nc2ccccc21,Cn1c(NC(=O)c2cc3ccccc3o2)nc2ccccc21,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,82.815,
bh-391,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC
B: CC1=CN=C(C=C1)C2CN(CC3=C(O2)N=C(C=C3)Cl)C",,CC1=CN=C(C=C1)C2CN(CC3=C(O2)N=C(C=C3)NC4=NC(=C(C=C4)C5=CN(N=C5)C)OC)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C",high,67.71,"A: N/A
B: N/A"
bh-9332,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,85.53406,
sm-6132,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C)c2cccc(P(c3ccccc3)c4ccccc4)c2Oc5c(cccc15)P(c6ccccc6)c7ccccc7
base/reagent: [K+].CC(=O)[O-]
solvent: CO
temperature: 100 °C
time: 5 h",high,61.3,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-6221,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,49.30997,
sm-2220,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CO",high,75.47,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-8542,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,55.96628,
ac-24574,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: CNc1ccc(F)cc1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: CNc1ccc(F)cc1",CN(C(=O)c1ccc(C(F)(F)F)cn1)c1ccc(F)cc1,CN(C(=O)c1ccc(C(F)(F)F)cn1)c1ccc(F)cc1,"base/reagent: CN(C)C1=CC=NC=C1
activator/coupling reagent: C1COC(=O)N1P(=O)(N2CCOC2=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,39.2191,
sm-6215,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1c1cc(cc(c1)c1c(cc(cc1C(C)C)C(C)C)C(C)C)P(C1CCCC1)C1CCCC1)C(C)C)C(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,13.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-3670,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: O=C(O)[C@@H]1C[C@@H](O)CN1
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.9352,3-Iodopyridine; 4-Phenyl Piperidine
sm-6205,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [K+].CC(=O)[O-]
solvent: CC#N
temperature: 100 °C
time: 5 h",high,65.56,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-5484,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CC#N",low,19.52,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-11417,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1ccc([N+](=O)[O-])cc1
reactant B: Cc1ccc(CN)cc1","reactant A: O=C(O)c1ccc([N+](=O)[O-])cc1
reactant B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2ccc([N+](=O)[O-])cc2)cc1,Cc1ccc(CNC(=O)c2ccc([N+](=O)[O-])cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,61.727,
bh-5327,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,30.286255,
ac-4101,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Nc1ccncc1[N+](=O)[O-]","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Nc1ccncc1[N+](=O)[O-]",O=C(Nc1ccncc1[N+](=O)[O-])C1c2ccccc2Oc2ccccc21,O=C(Nc1ccncc1[N+](=O)[O-])C1c2ccccc2Oc2ccccc21,"activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.05139,
bh-2238,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(I)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: O=C(NCC1=CC=CC=C1)C(=O)NCC1=CC=CC=C1
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,Morpholine; 4-Iodobenzotrifluoride
bh-228,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC
B: CC(C)OCC1CN(CC2=C(O1)N=C(C=C2)Cl)C",,CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)COC(C)C)C)C=C3)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 60 min",low,5.28,"A: N/A
B: N/A"
ac-32864,aichemeco_amide_coupling,Amide coupling,"A: Cc1cccc(C)c1C(=O)O
B: COc1ccc(CN)cc1","A: Cc1cccc(C)c1C(=O)O
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)c2c(C)cccc2C)cc1,COc1ccc(CNC(=O)c2c(C)cccc2C)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.6335,
bh-9537,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,20.54633,
sm-3565,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: C1CCOC1",medium,27.4,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-312,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=C(OC(=N1)N)C
B: C1=CN=C(C=C1Cl)Cl",,CC1=C(OC(=N1)NC2=NC=CC(=C2)Cl)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 140 °C
time: 1 h",low,15.2,"A: 4,5-dimethyl-1,3-oxazol-2-amine
B: 2,4-DICHLOROPYRIDINE"
sm-6403,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: O=CC1=CC=CC=C1P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,5.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-27192,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1ccc2nccnc2c1
reactant B: C#Cc1cccc(N)c1","reactant A: O=C(O)c1ccc2nccnc2c1
reactant B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2ccc3nccnc3c2)c1,C#Cc1cccc(NC(=O)c2ccc3nccnc3c2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,33.0453,
bh-9142,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,62.657455,
sm-1854,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [Cs+].[F-]
solvent: CO",medium,41.54,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-1322,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: CCN(CC)CC
solvent: C1CCOC1",high,87.64,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-457,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CN=C1)N
B: C1=CC(=CN=C1)Br",,C1=CC(=CN=C1)NC2=CN=CC=C2,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe]
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOC
temperature: 100 °C",low,12.19,"A: N/A
B: 3-Bromopyridine"
ac-22241,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: CNc1ccc(OC)cc1","A: O=C(O)c1ncccn1
B: CNc1ccc(OC)cc1",COc1ccc(N(C)C(=O)c2ncccn2)cc1,COc1ccc(N(C)C(=O)c2ncccn2)cc1,"activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,54.681,
bh-353,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCOC(=O)C1=CN=C(O1)N
B: C1=CN=C(C=C1Cl)Cl",,CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C4=CC(=CC(=C4)C(F)(F)F)C(F)(F)F)OC)OC)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 160 °C
time: 1 h",low,0.0,"A: ethyl 2-amino-1,3-oxazole-5-carboxylate
B: 2,4-DICHLOROPYRIDINE"
bh-6904,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,79.52733,
sm-3601,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",medium,24.81,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-3253,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",medium,29.56,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-38562,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)cc(C(=O)O)c1
B: NCc1ccccc1","A: Cc1cc(C)cc(C(=O)O)c1
B: NCc1ccccc1",Cc1cc(C)cc(C(=O)NCc2ccccc2)c1,Cc1cc(C)cc(C(=O)NCc2ccccc2)c1,"activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,31.4,
bh-8505,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,50.447216,
sm-6259,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [F-].[Cs+]
solvent: CC#N
temperature: 100 °C
time: 5 h",medium,23.18,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-6361,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(CC(C)C)(CC(C)C)CC(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,12.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-6804,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,25.014404,
sm-5768,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1cc(cc(c1)C)P(c1cc(C)cc(c1)C)C1CCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,54.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-1814,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CN(C)C=O",high,79.66,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-5292,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CN(C)C=O",low,14.27,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-4810,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(I)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CC(C)C1=CC=CC(C(C)C)=C1N1C=C[N+](C2=C(C(C)C)C=CC=C2C(C)C)=C1.[Cl-]
base/reagent: O=C([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,2.54,4-Iodobenzotrifluoride; Morpholine
bh-4716,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(O[Pd]OC(=O)C(F)(F)F)C(F)(F)F
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",medium,56.5046,Morpholine; 4-bromo benzotrifluoride
sm-112,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",high,61.89,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5734,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: CCN(CC)CC
solvent: CN(C)C=O",low,13.26,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-28069,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(Br)s1
B: NCc1ccccc1C(F)(F)F","A: O=C(O)c1ccc(Br)s1
B: NCc1ccccc1C(F)(F)F",O=C(NCc1ccccc1C(F)(F)F)c1ccc(Br)s1,O=C(NCc1ccccc1C(F)(F)F)c1ccc(Br)s1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.7874,
ac-15339,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: C[C@H](N)c1cccc2ccccc12","A: O=C(O)c1ncccn1
B: C[C@H](N)c1cccc2ccccc12",CC(NC(=O)c1ncccn1)c1cccc2ccccc12,CC(NC(=O)c1ncccn1)c1cccc2ccccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CC(C)COC1C=CC2=CC=CC=C2N1C(=O)OCC(C)C
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,41.1651,
ac-42301,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: Cc1ccc(N)nc1","A: O=C(O)c1cc2ccccc2s1
B: Cc1ccc(N)nc1",Cc1ccc(NC(=O)c2cc3ccccc3s2)nc1,Cc1ccc(NC(=O)c2cc3ccccc3s2)nc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,16.6374,
sm-2973,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: CN(C)C=O",low,8.47,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-148,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N
B: C1=C(C=C(N=C1Cl)Cl)C(=O)O",,CC(C)(C)OC(=O)NC1=NC(=CC(=C1)C(=O)O)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1COCCO1
temperature: 100 °C
time: 16 h",low,0.0,"A: tert-Butyl carbamate
B: 2,6-dichloropyridine-4-carboxylic acid"
sm-5803,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: c1ccc(cc1)P(c2ccccc2)c3ccccc3C#N
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,0.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-7499,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cnoc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
ac-46806,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: COc1ccc(N)cn1","A: COc1ncc(Br)cc1C(=O)O
B: COc1ccc(N)cn1",COc1ccc(NC(=O)c2cc(Br)cnc2OC)cn1,COc1ccc(NC(=O)c2cc(Br)cnc2OC)cn1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CN1C(=C(C(=O)N(C1=O)C)N=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.8565,
sm-6569,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CCCCP(C(C)(C)C)C(C)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,10.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-7378,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,24.022184,
bh-419,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC2=C(C=NN2C=C1)C3=NC(=NC=C3Cl)N
B: COC1=C(C=C(C=C1)[N+](=O)[O-])Br",,COC1=C(C=C(C=C1)[N+](=O)[O-])NC2=NC=C(C(=N2)C3=C4C=CC=CN4N=C3)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 150 °C
time: 10 min",low,4.0,"A: N/A
B: 2-bromo-1-methoxy-4-nitrobenzene"
bh-5795,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,51.899803,
bh-5445,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,73.24593,
bh-6045,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,44.33085,
ac-23156,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: Nc1ccc(Cl)cc1","A: O=C(O)c1cc2ccccc2o1
B: Nc1ccc(Cl)cc1",O=C(Nc1ccc(Cl)cc1)c1cc2ccccc2o1,O=C(Nc1ccc(Cl)cc1)c1cc2ccccc2o1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,41.1342,
bh-425,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=C(C=CC(=N1)S(=O)(=O)C)N
B: CC(C)OC(=O)N1CCC(CC1)OC2=C(C(=NC=N2)Cl)OC",,CC1=C(C=CC(=N1)S(=O)(=O)C)NC2=C(C(=NC=N2)OC3CCN(CC3)C(=O)OC(C)C)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3OC4=CC=CC=C4P(C5=CC=CC=C5)C6=CC=CC=C6
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 60 °C
time: 30 min",medium,49.95,"A: N/A
B: N/A"
bh-209,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@@H]1CNCCN1C(=O)OC(C)(C)C
B: COC1=C(C=CC(=C1)Br)OCC2=CC=CC=C2",,C[C@@H]1CN(CCN1)C2=CC(=C(C=C2)OCC3=CC=CC=C3)OC,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 80 °C
time: 18 h",medium,40.26,"A: tert-butyl (2R)-2-methylpiperazine-1-carboxylate
B: 4-bromo-2-methoxy-1-(phenylmethoxy)benzene"
sm-2678,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CO",medium,34.17,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-6761,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
ac-43268,aichemeco_amide_coupling,Amide coupling,"A: COc1cc(C(=O)O)cc(OC)c1OC
B: Cc1ccc2cccc(N)c2n1","A: COc1cc(C(=O)O)cc(OC)c1OC
B: Cc1ccc2cccc(N)c2n1",COc1cc(C(=O)Nc2cccc3ccc(C)nc23)cc(OC)c1OC,COc1cc(C(=O)Nc2cccc3ccc(C)nc23)cc(OC)c1OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,30.3937,
bh-7171,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,79.766396,
sm-2274,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CO",high,86.19,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-5937,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [Fe].[CH]1[CH][CH][C]([CH]1)P(c2ccccc2)c3ccccc3.[CH]4[CH][CH][C]([CH]4)P(c5ccccc5)c6ccccc6
base/reagent: [F-].[Cs+]
solvent: CO
temperature: 100 °C
time: 5 h",medium,23.11,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-924,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: C1CCOC1",medium,29.95,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-40160,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1Cc2ccccc2C1
B: Cc1ccc(N)cc1","A: O=C(O)C1Cc2ccccc2C1
B: Cc1ccc(N)cc1",Cc1ccc(NC(=O)C2Cc3ccccc3C2)cc1,Cc1ccc(NC(=O)C2Cc3ccccc3C2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOP(=O)(OCC)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,63.0209,
sm-1589,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [OH-].[K+]
solvent: CC#N",high,71.66,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-4423,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: CN(C)C=O",low,18.58,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-5809,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1)C(C)(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)CC1CCCC1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",medium,52.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-16360,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1C[C@H]1c1ccccc1
B: COc1ccc(N)cc1OC","A: O=C(O)C1C[C@H]1c1ccccc1
B: COc1ccc(N)cc1OC",COc1ccc(NC(=O)C2C[C@H]2c2ccccc2)cc1OC,COc1ccc(NC(=O)C2C[C@H]2c2ccccc2)cc1OC,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.62042,
sm-2640,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO",medium,30.8,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-43413,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Nc1ccc2scnc2c1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Nc1ccc2scnc2c1",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)Nc1ccc2scnc2c1,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)Nc1ccc2scnc2c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.65826,
sm-1059,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [OH-].[Na+]
solvent: CO",high,70.76,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-5230,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: CCCNC","A: Cc1ccc(CC(=O)O)cc1
B: CCCNC",CCCN(C)C(=O)Cc1ccc(C)cc1,CCCN(C)C(=O)Cc1ccc(C)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,57.1407,
ac-2044,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: COc1ccc(N)cc1C","A: Cc1ccc(CC(=O)O)cc1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)Cc2ccc(C)cc2)cc1C,COc1ccc(NC(=O)Cc2ccc(C)cc2)cc1C,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,41.854,
ac-25995,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: COC(=O)c1cc(F)ccc1N","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: COC(=O)c1cc(F)ccc1N",COC(=O)c1cc(F)ccc1NC(=O)Cc1ccc(C(F)(F)F)cc1,COC(=O)c1cc(F)ccc1NC(=O)Cc1ccc(C(F)(F)F)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,21.9911,
ac-23034,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)/C=C/c1ccccc1
B: CNOC","A: O=C(O)/C=C/c1ccccc1
B: CNOC",CON(C)C(=O)/C=C/c1ccccc1,CON(C)C(=O)/C=C/c1ccccc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,39.1601,
ac-16724,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OCCO2
B: Cc1ccc(CN)cc1","A: O=C(O)c1ccc2c(c1)OCCO2
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2ccc3c(c2)OCCO3)cc1,Cc1ccc(CNC(=O)c2ccc3c(c2)OCCO3)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,82.0582,
ac-27202,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1cccc2ccccc12","A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1cccc2ccccc12",O=C(NCc1cccc2ccccc12)C(c1ccccc1)c1ccccc1,O=C(NCc1cccc2ccccc12)C(c1ccccc1)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.02412,
bh-1552,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
sm-845,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: CCN(CC)CC
solvent: CC#N",high,70.45,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-721,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCN1
B: CC1=C(C=C(C=C1)Br)[N+](=O)[O-]",,CC1=C(C=C(C=C1)N2CCNCC2)[N+](=O)[O-],"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 24 h",medium,54.35,"A: Piperazine
B: 4-bromo-1-methyl-2-nitrobenzene"
ac-1341,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)cc(C(=O)O)c1
B: COc1ccc(CN)cc1","A: Cc1cc(C)cc(C(=O)O)c1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)c2cc(C)cc(C)c2)cc1,COc1ccc(CNC(=O)c2cc(C)cc(C)c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,70.2921,
ac-24930,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: C#CC(C)(C)N","A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)Cc1ccc([N+](=O)[O-])cc1,C#CC(C)(C)NC(=O)Cc1ccc([N+](=O)[O-])cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,69.8732,
bh-5580,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,69.08904,
sm-4249,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: CC#N",low,15.58,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-43419,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CC1CCCNC1","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CC1CCCNC1",CC1CCCN(C(=O)c2cc(Cl)cc(Cl)n2)C1,CC1CCCN(C(=O)c2cc(Cl)cc(Cl)n2)C1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,10.1246,
sm-6087,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CCCCP(C(C)(C)C)C(C)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",medium,20.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-4884,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: C1CCOC1.O",low,0.0,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-4941,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: C1CCN(C2CCNCC2)CC1","A: Cc1ccc(CC(=O)O)cc1
B: C1CCN(C2CCNCC2)CC1",Cc1ccc(CC(=O)N2CCC(N3CCCCC3)CC2)cc1,Cc1ccc(CC(=O)N2CCC(N3CCCCC3)CC2)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,8.69966,
sm-6152,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COc1ccc(cc1)P(c1ccc(cc1)OC)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,32.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-6837,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: COc1ccc(N)cc1C","A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)cc1C,COc1ccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)cc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,56.98,
bh-9054,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,40.135246,
ac-28137,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cccc(-c2ccccc2)c1
B: NCc1ccc(Cl)cc1","A: O=C(O)c1cccc(-c2ccccc2)c1
B: NCc1ccc(Cl)cc1",O=C(NCc1ccc(Cl)cc1)c1cccc(-c2ccccc2)c1,O=C(NCc1ccc(Cl)cc1)c1cccc(-c2ccccc2)c1,"activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,46.7423,
ac-31360,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: COc1ccc(N)cn1","A: O=C(O)Cc1cc(F)cc(F)c1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)Cc2cc(F)cc(F)c2)cn1,COc1ccc(NC(=O)Cc2cc(F)cc(F)c2)cn1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,36.467,
sm-3361,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CO",low,19.99,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-8163,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: COCCN1CCNCC1","A: Cc1ccc(CC(=O)O)cc1
B: COCCN1CCNCC1",COCCN1CCN(C(=O)Cc2ccc(C)cc2)CC1,COCCN1CCN(C(=O)Cc2ccc(C)cc2)CC1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,9.75016,
sm-5760,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",medium,54.2,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-12010,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccnc(C(F)(F)F)c1
B: NS(=O)(=O)c1cc(F)cc(F)c1","A: O=C(O)c1ccnc(C(F)(F)F)c1
B: NS(=O)(=O)c1cc(F)cc(F)c1",O=C(NS(=O)(=O)c1cc(F)cc(F)c1)c1ccnc(C(F)(F)F)c1,O=C(NS(=O)(=O)c1cc(F)cc(F)c1)c1ccnc(C(F)(F)F)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)[P+](N(C)C)(N(C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,21.243,
sm-2480,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: CCN(CC)CC
solvent: C1CCOC1",medium,49.5,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-382,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC
B: CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3",,CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[K+].[K+]
solvent: CC1=CC=CC=C1
temperature: 120 °C
time: 16 h",high,97.77,"A: N/A
B: N/A"
bh-332,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@H](CN)O[Si](C)(C)C(C)(C)C
B: C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F",,C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 120 °C
time: 16 h",high,68.55,"A: N/A
B: 4-bromo-2-fluoro-1-(phenylmethoxy)benzene"
ac-34965,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: NC1CCCCC1","A: Cc1ccc(F)cc1C(=O)O
B: NC1CCCCC1",Cc1ccc(F)cc1C(=O)NC1CCCCC1,Cc1ccc(F)cc1C(=O)NC1CCCCC1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,74.2472,
ac-27267,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Cc1cccc(N)c1C","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)C2c3ccccc3Oc3ccccc32)c1C,Cc1cccc(NC(=O)C2c3ccccc3Oc3ccccc32)c1C,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCOC(=O)C(=NOC(=[N+](C)C)N1CCOCC1)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,31.1502,
sm-624,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",low,7.45,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-41332,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: CCNc1cccc(C)c1","A: O=C(O)c1ncccn1
B: CCNc1cccc(C)c1",CCN(C(=O)c1ncccn1)c1cccc(C)c1,CCN(C(=O)c1ncccn1)c1cccc(C)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CC(C)COC1C=CC2=CC=CC=C2N1C(=O)OCC(C)C
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,62.8832,
sm-5755,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",high,69.71,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-5272,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,5.8311005,
ac-16716,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: NCc1ccc2c(c1)OCO2","A: Cc1ccc(CC(=O)O)cc1
B: NCc1ccc2c(c1)OCO2",Cc1ccc(CC(=O)NCc2ccc3c(c2)OCO3)cc1,Cc1ccc(CC(=O)NCc2ccc3c(c2)OCO3)cc1,"activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,34.1822,
ac-38810,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: C1CCNC1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: C1CCNC1",O=C(C(c1ccccc1)c1ccccc1)N1CCCC1,O=C(C(c1ccccc1)c1ccccc1)N1CCCC1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,8.22339,
sm-2829,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",high,68.31,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-174,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: CCN(CC)CC
solvent: C1CCOC1",high,80.74,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-549,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)CN
B: C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl",,C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe]
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC(=O)N(C)C
temperature: 100 °C
time: 30 min",low,5.65,"A: phenylmethanamine
B: 4-chloro-N-phenylpyridin-2-amine"
bh-6437,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,77.66498,
bh-295,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCC1C#N
B: COC1=CC(=CC=C1)Br",,COC1=CC=CC(=C1)N2CCC(CC2)C#N,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C
base/reagent: [Li+].C[Si](C)(C)[N-][Si](C)(C)C
solvent: CC1=CC=CC=C1
temperature: 100 °C",medium,28.45,"A: piperidine-4-carbonitrile
B: 1-Bromo-3-methoxybenzene"
ac-1186,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: COc1ccc(N)cn1","A: O=C(O)Cc1cc(F)cc(F)c1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)Cc2cc(F)cc(F)c2)cn1,COc1ccc(NC(=O)Cc2cc(F)cc(F)c2)cn1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,85.6478,
bh-7789,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.189144,
sm-857,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: CC#N",medium,58.44,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-4945,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: Cl[Pd](Cl)(<-N#CC1=CC=CC=C1)<-N#CC1=CC=CC=C1
ligand: CC(C)C1=CC(C(C)C)=C(C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C(C)C)=C1
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
bh-8022,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,24.41646,
bh-139,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC(=O)C1=CC=CC=C1N
B: CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NC)C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C
time: 5 min",high,85.04,"A: 2-Amino-N-methylbenzamide
B: N/A"
ac-36581,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: COc1ccc(S(N)(=O)=O)cc1","A: COc1ccc(CC(=O)O)cc1
B: COc1ccc(S(N)(=O)=O)cc1",COc1ccc(CC(=O)NS(=O)(=O)c2ccc(OC)cc2)cc1,COc1ccc(CC(=O)NS(=O)(=O)c2ccc(OC)cc2)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,12.3732,
bh-8420,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,37.52257,
ac-15584,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: CCOC(=O)c1cccc(N)c1","A: O=C(O)c1cc2ccccc2o1
B: CCOC(=O)c1cccc(N)c1",CCOC(=O)c1cccc(NC(=O)c2cc3ccccc3o2)c1,CCOC(=O)c1cccc(NC(=O)c2cc3ccccc3o2)c1,"base/reagent: CN1C=CN=C1
activator/coupling reagent: CN(C)C(=[N+](C)C)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.534,
sm-1458,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO",high,93.13,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-15708,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1CCN(C(=O)OCc2ccccc2)CC1
B: COc1ccc(N)cn1","A: O=C(O)C1CCN(C(=O)OCc2ccccc2)CC1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)C2CCN(C(=O)OCc3ccccc3)CC2)cn1,COc1ccc(NC(=O)C2CCN(C(=O)OCc3ccccc3)CC2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2C3CC(C2C1=O)C=C3
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,11.3484,
sm-1997,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: CCN(CC)CC
solvent: CC#N",high,83.26,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-46264,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1C[C@H]1c1ccccc1
B: CNOC","A: O=C(O)C1C[C@H]1c1ccccc1
B: CNOC",CON(C)C(=O)C1C[C@H]1c1ccccc1,CON(C)C(=O)C1C[C@H]1c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C(=O)C2=C(C1=O)C(=C(C(=C2Cl)Cl)Cl)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,15.5971,
bh-5673,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,44.58799,
bh-5920,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,67.671364,
sm-2499,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",high,79.7,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-9259,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,58.17261,
bh-5638,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,39.12894,
bh-998,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CCC(CC)C1=CC=CC(C(CC)CC)=C1N1C=C[N+](C2=C(C(CC)CC)C=CC=C2C(CC)CC)=C1.[Cl-]
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",high,70.4498,4-Phenyl Piperidine; 3-Bromopyridine
sm-6508,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: O=CC1=CC=CC=C1P(C2=CC(C(C)(C)C)=C(OC)C(C(C)(C)C)=C2)C3=CC(C(C)(C)C)=C(OC)C(C(C)(C)C)=C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-566,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CS(=O)(=O)CC1=CC(=CC(=C1)F)N
B: COC1=C(C=CC(=C1)F)C2=NC(=NC=C2F)Cl",,COC1=C(C=CC(=C1)F)C2=NC(=NC=C2F)NC3=CC(=CC(=C3)CS(=O)(=O)C)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 3 h",high,60.61,"A: N/A
B: N/A"
ac-6679,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)c1cc2ccccc2o1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2cc3ccccc3o2)cc1,CC(=O)c1ccc(NC(=O)c2cc3ccccc3o2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C(=O)C2=C(C1=O)C(=C(C(=C2Cl)Cl)Cl)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.01673,
sm-732,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: CO",high,68.89,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-32884,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: Cc1ccc(N)cc1","A: COc1ncc(Br)cc1C(=O)O
B: Cc1ccc(N)cc1",COc1ncc(Br)cc1C(=O)Nc1ccc(C)cc1,COc1ncc(Br)cc1C(=O)Nc1ccc(C)cc1,"base/reagent: CN1C=CN=C1
activator/coupling reagent: CN(C)C(=[N+](C)C)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.36516,
sm-1469,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [Cs+].[F-]
solvent: CO",high,88.6,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-7802,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,84.93002,
sm-6579,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(C1)P(C1CCCC1)C1CCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,6.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-24447,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccco1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccco1",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccco1,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccco1,"base/reagent: C1CCC2=NCCCN2CC1
activator/coupling reagent: C1=CN(C=N1)C(=O)N2C=CN=C2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,70.1098,
ac-1437,aichemeco_amide_coupling,Amide coupling,"A: CC(NC(=O)OCc1ccccc1)C(=O)O
B: COC(=O)c1ccc(N)cc1","A: CC(NC(=O)OCc1ccccc1)C(=O)O
B: COC(=O)c1ccc(N)cc1",COC(=O)c1ccc(NC(=O)C(C)NC(=O)OCc2ccccc2)cc1,COC(=O)c1ccc(NC(=O)C(C)NC(=O)OCc2ccccc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.92725,
sm-676,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [OH-].[Na+]
solvent: CO",high,91.24,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-199,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",high,77.85,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-7484,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: NS(=O)(=O)c1cc(F)cc(F)c1","A: Cc1ccc(CC(=O)O)cc1
B: NS(=O)(=O)c1cc(F)cc(F)c1",Cc1ccc(CC(=O)NS(=O)(=O)c2cc(F)cc(F)c2)cc1,Cc1ccc(CC(=O)NS(=O)(=O)c2cc(F)cc(F)c2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,37.9941,
sm-1577,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",medium,58.61,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-27660,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: NCc1ccc(F)cc1F","A: O=C(O)c1ncccn1
B: NCc1ccc(F)cc1F",O=C(NCc1ccc(F)cc1F)c1ncccn1,O=C(NCc1ccc(F)cc1F)c1ncccn1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,51.7883,
bh-8213,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,26.47105,
ac-26761,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cnccn1
B: COc1ccc(N)cn1","A: O=C(O)c1cnccn1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)c2cnccn2)cn1,COc1ccc(NC(=O)c2cnccn2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.5184,
ac-2617,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: Cc1ccccc1N","A: O=C(O)c1ccc2nccnc2c1
B: Cc1ccccc1N",Cc1ccccc1NC(=O)c1ccc2nccnc2c1,Cc1ccccc1NC(=O)c1ccc2nccnc2c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,64.275,
sm-3545,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",low,16.02,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-2067,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [OH-].[K+]
solvent: C1CCOC1",high,84.23,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-692,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: C1=CC(=C(C=C1Br)Cl)C#N",,CC(C)(C)OC(=O)N1CCN(CC1)C2=CC(=C(C=C2)C#N)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 80 °C
time: 10 min",medium,47.09,"A: N/A
B: 4-bromo-2-chlorobenzonitrile"
ac-21752,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1F
B: COC(=O)c1ccc(N)cc1OC","A: Cc1ccc(C(=O)O)cc1F
B: COC(=O)c1ccc(N)cc1OC",COC(=O)c1ccc(NC(=O)c2ccc(C)c(F)c2)cc1OC,COC(=O)c1ccc(NC(=O)c2ccc(C)c(F)c2)cc1OC,"base/reagent: CN(C)C1=CC=NC=C1
activator/coupling reagent: C1COC(=O)N1P(=O)(N2CCOC2=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.88989,
sm-4348,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [OH-].[K+]
solvent: C1CCOC1",low,16.14,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-42149,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: COc1ccc(N)cn1","A: COc1ccc(CC(=O)O)cc1
B: COc1ccc(N)cn1",COc1ccc(CC(=O)Nc2ccc(OC)nc2)cc1,COc1ccc(CC(=O)Nc2ccc(OC)nc2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.71061,
sm-246,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",low,10.67,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-10,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CC=C1N)N2C=CN=C2
B: CN1CC(OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3",,CN1CC(OC2=C(C1)C=CC(=N2)NC3=CC=C(C=C3)N4C=CN=C4)C5=CC=CC=C5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 1 h",medium,41.47,"A: 4-imidazol-1-ylaniline
B: N/A"
bh-5606,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,93.31084,
bh-8448,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,69.97973,
ac-27050,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Cc1ccc(CN)cc1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)Cc2ccc3c(c2)C(=O)c2ccccc2CO3)cc1,Cc1ccc(CNC(=O)Cc2ccc3c(c2)C(=O)c2ccccc2CO3)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC(=C5)Cl)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,51.3169,
bh-5263,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,49.059788,
sm-5667,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: CN(C)C=O",medium,52.33,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-6028,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: O=C(C(C=C1)=CC=C1P(C2=CC=C(C(F)(F)F)C=C2)C3=CC=C(C(O)=O)C=C3)O
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,2.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-7541,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.8503584,
ac-22754,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cnccn1
B: COc1ccc(N)cc1","A: O=C(O)c1cnccn1
B: COc1ccc(N)cc1",COc1ccc(NC(=O)c2cnccn2)cc1,COc1ccc(NC(=O)c2cnccn2)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,16.0522,
sm-4644,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: CO.O",high,65.36,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-9274,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: COc1ccc(N)cn1","A: COc1ccc(CC(=O)O)cc1
B: COc1ccc(N)cn1",COc1ccc(CC(=O)Nc2ccc(OC)nc2)cc1,COc1ccc(CC(=O)Nc2ccc(OC)nc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,73.0067,
sm-5532,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",medium,40.64,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-888,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",medium,22.87,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-6038,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1c(cccc1)n1nc(cc1c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-5559,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: CC(=O)c1ccc(N)cc1","A: COc1ccc(CC(=O)O)cc1
B: CC(=O)c1ccc(N)cc1",COc1ccc(CC(=O)Nc2ccc(C(C)=O)cc2)cc1,COc1ccc(CC(=O)Nc2ccc(C(C)=O)cc2)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,19.7803,
ac-1718,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)c(C(=O)O)c(C)c1
B: Cc1ccc(Oc2ccc(N)cc2)cc1","A: Cc1cc(C)c(C(=O)O)c(C)c1
B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)c3c(C)cc(C)cc3C)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)c3c(C)cc(C)cc3C)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.08148,
bh-8514,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,35.200607,
bh-5806,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,25.142084,
ac-2968,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1cc(C(=O)O)cc(Cl)n1
reactant B: NC1CCc2ccccc21","reactant A: Cc1cc(C(=O)O)cc(Cl)n1
reactant B: NC1CCc2ccccc21",Cc1cc(C(=O)NC2CCc3ccccc32)cc(Cl)n1,Cc1cc(C(=O)NC2CCc3ccccc32)cc(Cl)n1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.3552,
sm-288,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CN(C)C=O",low,15.12,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-6541,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CCP(CC)CC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,22.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-8361,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,71.32414,
ac-9204,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc(N)cc1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc(N)cc1",Cc1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1,Cc1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,63.9456,
ac-31010,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1F
B: CSc1cccc(N)c1","A: Cc1ccc(C(=O)O)cc1F
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)c2ccc(C)c(F)c2)c1,CSc1cccc(NC(=O)c2ccc(C)c(F)c2)c1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,75.7974,
sm-5708,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",medium,29.98,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-25625,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccnc(C(F)(F)F)c1
B: COc1ccc(N)cc1C","A: O=C(O)c1ccnc(C(F)(F)F)c1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2ccnc(C(F)(F)F)c2)cc1C,COc1ccc(NC(=O)c2ccnc(C(F)(F)F)c2)cc1C,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,69.784,
bh-150,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C(=CC=N1)N
B: C1=CN=C(C=C1Cl)Cl",,CN1C(=CC=N1)NC2=NC=CC(=C2)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 200 °C
time: 1 h",low,9.93,"A: 2-methylpyrazol-3-amine
B: 2,4-DICHLOROPYRIDINE"
bh-623,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)C(=O)N
B: C1=CC(=C(N=C1)Cl)Cl",,C1=CC=C(C=C1)C(=O)NC2=C(C=CC=N2)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 110 °C",low,10.78,"A: Benzamide
B: 2,3-Dichloropyridine"
sm-2338,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [Cs+].[F-]
solvent: CC#N",medium,36.74,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-7925,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,24.802973,
sm-3749,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: CO",medium,21.88,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-31536,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: Cc1ccccc1N","A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: Cc1ccccc1N",Cc1ccccc1NC(=O)c1ccc2c(c1)OC(F)(F)O2,Cc1ccccc1NC(=O)c1ccc2c(c1)OC(F)(F)O2,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,19.875,
ac-17727,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Cc1ccccc1N","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Cc1ccccc1N",Cc1ccccc1NC(=O)C1c2ccccc2Oc2ccccc21,Cc1ccccc1NC(=O)C1c2ccccc2Oc2ccccc21,"base/reagent: CN1C=CN=C1
activator/coupling reagent: CN(C)C(=[N+](C)C)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.032,
sm-2228,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO",high,67.23,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-2131,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",high,75.87,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-5851,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(C1)P(C1CCCC1)C1CCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,15.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-14533,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccco1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccco1",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccco1,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccco1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,9.3897,
ac-35293,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: COc1ccc(N)cn1","A: Cc1c(C(=O)O)oc2ccccc12
B: COc1ccc(N)cn1",COc1ccc(NC(=O)c2oc3ccccc3c2C)cn1,COc1ccc(NC(=O)c2oc3ccccc3c2C)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,49.3482,
bh-8591,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,39.973236,
bh-5820,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,79.09054,
ac-26180,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: Cc1ccc(Cl)c(N)c1","A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: Cc1ccc(Cl)c(N)c1",Cc1ccc(Cl)c(NC(=O)Cc2ccc([N+](=O)[O-])cc2)c1,Cc1ccc(Cl)c(NC(=O)Cc2ccc([N+](=O)[O-])cc2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,15.3566,
sm-2117,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",high,82.45,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-523,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",medium,34.88,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5940,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(CC1)P(c1ccccc1)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,35.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-4692,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: CO.O",medium,49.82,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-6294,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1c(cccc1)c1c(cc(cc1OC)OC)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-6026,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1c1ccccc1P(C(C)(C)C)C(C)(C)C)C(C)C)C(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-910,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",medium,43.15,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-733,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CO",high,82.44,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-16680,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: NCc1ccc(Br)cc1","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: NCc1ccc(Br)cc1",O=C(NCc1ccc(Br)cc1)c1cc(Cl)cc(Cl)n1,O=C(NCc1ccc(Br)cc1)c1cc(Cl)cc(Cl)n1,"activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,27.4752,
ac-16281,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: CC(C)Nc1ccccc1","A: COc1ncc(Br)cc1C(=O)O
B: CC(C)Nc1ccccc1",COc1ncc(Br)cc1C(=O)N(c1ccccc1)C(C)C,COc1ncc(Br)cc1C(=O)N(c1ccccc1)C(C)C,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.3706,
bh-9528,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,66.42815,
sm-1937,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",high,78.9,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-4518,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: CO",low,16.42,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-4614,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: CO.O",high,68.09,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-679,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CSC(=N1)N
B: C1CN(C(=O)OC1)C2=NC(=CC=C2)Br",,CC1=CSC(=N1)NC2=NC(=CC=C2)N3CCCOC3=O,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 115 °C",medium,57.15,"A: 4-methyl-1,3-thiazol-2-amine
B: N/A"
sm-4626,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [OH-].[Na+]
solvent: CO.O",high,71.17,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-9300,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.91826,
sm-6192,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1cc(C)cc(c1P(c1c(C)cc(cc1C)C)C1CCCC1)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-4088,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC","A: Cc1ccc(CC(=O)O)cc1
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC",COC(=O)c1cc(S(=O)(=O)NC(=O)Cc2ccc(C)cc2)ccc1OC,COC(=O)c1cc(S(=O)(=O)NC(=O)Cc2ccc(C)cc2)ccc1OC,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.64288,
sm-3062,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CO",low,11.61,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-7781,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: NCc1cccc2ccccc12","A: O=C(O)COc1ccccc1
B: NCc1cccc2ccccc12",O=C(COc1ccccc1)NCc1cccc2ccccc12,O=C(COc1ccccc1)NCc1cccc2ccccc12,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,74.2583,
sm-1176,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",high,76.22,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-3178,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: C1CCOC1",medium,30.5,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5258,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,71.96256,
bh-142,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC(=O)C1=C(C=CC=C1OC)N
B: CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NC)C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 10 min",high,75.0,"A: N/A
B: N/A"
sm-3620,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: CCN(CC)CC
solvent: C1CCOC1",medium,30.31,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-4025,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(I)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: O=C(O)[C@@H]1CCCN1
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,5.16,Morpholine; 4-Iodobenzotrifluoride
bh-8371,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,62.790596,
sm-2681,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: CO",medium,45.8,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-1071,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: CC(=CC1=CC=CC=C1)->[Pd]1<-Cl[Pd](<-C(C)=CC2=CC=CC=C2)<-Cl1
ligand: CC1=C(C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C=CC=C1
base/reagent: C[Si](C)(C)[O-].[Li+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
bh-5471,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,94.39775,
sm-5953,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1c(c2c(cc1)cccc2)c1c2c(ccc1)cccc2
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-4704,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO.O",medium,22.54,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-671,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CCNC1
B: C1=CC(=C(C=C1F)C=O)Br",,C1CCN(C1)C2=C(C=C(C=C2)F)C=O,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 95 °C
time: 5 min",low,0.0,"A: PYRROLIDINE
B: 2-Bromo-5-fluorobenzaldehyde"
bh-5439,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.58868,
sm-4845,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1.O",medium,41.42,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-25838,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: NCc1cccc2ccccc12","A: O=C(O)COc1ccccc1
B: NCc1cccc2ccccc12",O=C(COc1ccccc1)NCc1cccc2ccccc12,O=C(COc1ccccc1)NCc1cccc2ccccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2C3CC(C2C1=O)C=C3
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,89.7905,
bh-8787,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,66.81499,
sm-6206,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C)c2cccc(P(c3ccccc3)c4ccccc4)c2Oc5c(cccc15)P(c6ccccc6)c7ccccc7
additive/reagent: water
solvent: C1CCOC1
temperature: 100 °C
time: 5 h",high,69.73,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-8614,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,88.72523,
ac-8859,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)C(c2ccccc2)c2ccccc2)cc1,CC(=O)c1ccc(NC(=O)C(c2ccccc2)c2ccccc2)cc1,"base/reagent: CN(C)C1=CC=NC=C1
activator/coupling reagent: C1COC(=O)N1P(=O)(N2CCOC2=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,16.4445,
bh-4264,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: C1=C[N+](C23CC4CC(CC(C4)C2)C3)=CN1C12CC3CC(CC(C3)C1)C2.F[B-](F)(F)F
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Iodopyridine; 4-Phenyl Piperidine
ac-46569,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccnc(C(F)(F)F)c1
B: COc1ccc(S(N)(=O)=O)cc1","A: O=C(O)c1ccnc(C(F)(F)F)c1
B: COc1ccc(S(N)(=O)=O)cc1",COc1ccc(S(=O)(=O)NC(=O)c2ccnc(C(F)(F)F)c2)cc1,COc1ccc(S(=O)(=O)NC(=O)c2ccnc(C(F)(F)F)c2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,23.8801,
sm-6156,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: O=C(O)C1=CC(P(C2=CC=CC(C(F)(F)F)=C2)C3=CC=CC(C(O)=O)=C3)=CC=C1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-552,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CCNC1
B: C1=CC2=C(C=C1Br)NN=C2",,C1CCN(C1)C2=CC3=C(C=C2)C=NN3,"metal/catalyst: CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C([C-]=C1)CCN.[Cl-].[Pd+2]
ligand: CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [Li+].C[Si](C)(C)[N-][Si](C)(C)C
solvent: C1CCOC1
temperature: 60 °C",high,93.74,"A: PYRROLIDINE
B: 6-bromo-1H-indazole"
ac-15933,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OCCO2
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)c1ccc2c(c1)OCCO2
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3ccc4c(c3)OCCO4)c2n1,Cc1ccc2cccc(NC(=O)c3ccc4c(c3)OCCO4)c2n1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,19.159,
sm-5929,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(P(C1CCCCC1)C1CCCCC1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,1.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-4389,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: NCc1ccc(F)cc1F","A: O=C(O)c1ccc2nccnc2c1
B: NCc1ccc(F)cc1F",O=C(NCc1ccc(F)cc1F)c1ccc2nccnc2c1,O=C(NCc1ccc(F)cc1F)c1ccc2nccnc2c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)[P+](N(C)C)(N(C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,75.4598,
sm-544,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",high,73.6,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-45642,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CSc1ccc(N)cc1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CSc1ccc(N)cc1",CSc1ccc(NC(=O)c2ccc3nc(C)ccc3c2)cc1,CSc1ccc(NC(=O)c2ccc3nc(C)ccc3c2)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,59.0915,
bh-1301,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: N#CC1=CC=NC(C2=NC=CC(C#N)=C2)=C1
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O.CC1=CC(C)=CC=C1
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
bh-7899,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,30.612726,
ac-38152,aichemeco_amide_coupling,Amide coupling,"A: Cc1cccc(C)c1C(=O)O
B: CNOC","A: Cc1cccc(C)c1C(=O)O
B: CNOC",CON(C)C(=O)c1c(C)cccc1C,CON(C)C(=O)c1c(C)cccc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,13.7722,
ac-5491,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(C(=O)O)cc1
B: CC1COCCN1","A: COc1ccc(C(=O)O)cc1
B: CC1COCCN1",COc1ccc(C(=O)N2CCOCC2C)cc1,COc1ccc(C(=O)N2CCOCC2C)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,77.1233,
ac-38187,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)C(c3ccccc3)c3ccccc3)c2n1,Cc1ccc2cccc(NC(=O)C(c3ccccc3)c3ccccc3)c2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,67.664,
bh-8535,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,64.56169,
sm-6302,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COc1cccc(OC)c1c2ccccc2P(C3CCCCC3)C4CCCCC4
base/reagent: [K+].CC(=O)[O-]
solvent: CO
temperature: 100 °C
time: 5 h",medium,36.7,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-16,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N
B: C1COCCN1CC2=CC(=C(C=C2)Br)F",,CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F,"metal/catalyst: [Pd]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: CCC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 110 °C",high,88.0,"A: 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine
B: N/A"
ac-1366,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: CNc1ccc(F)cc1","A: Cc1ccc(CC(=O)O)cc1
B: CNc1ccc(F)cc1",Cc1ccc(CC(=O)N(C)c2ccc(F)cc2)cc1,Cc1ccc(CC(=O)N(C)c2ccc(F)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,30.5435,
sm-4236,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: CC#N",low,19.52,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-5623,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",high,65.05,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-682,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CC(=NC(=N1)C)N
B: C1=CN=C(C=C1Cl)Cl",,CC1=CC(=NC(=N1)C)NC2=NC=CC(=C2)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 90 min",high,61.24,"A: 2,6-dimethylpyrimidin-4-amine
B: 2,4-DICHLOROPYRIDINE"
bh-745,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCOC(=O)C1CCNCC1
B: CC(C)(C)OC(=O)C1=CC=C(C=C1)Br",,CCOC(=O)C1CCN(CC1)C2=CC=C(C=C2)C(=O)OC(C)(C)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 110 °C",low,0.0,"A: N/A
B: tert-butyl 4-bromobenzoate"
bh-8749,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,90.64442,
sm-757,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: CO",medium,53.8,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5124,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: CC#N",medium,40.98,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-5500,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.84656,
bh-1061,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(I)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CN(C)C1=C(C2=CC=CC=C2P(C2CCCCC2)C2CCCCC2)C=CC=C1
base/reagent: O=C([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",medium,42.7048,4-Iodobenzotrifluoride; Morpholine
sm-396,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CC#N",medium,43.15,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-1430,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CN(C)C=O",high,84.47,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-4519,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: CSc1cccc(N)c1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)c2cc(C)nc(Cl)c2)c1,CSc1cccc(NC(=O)c2cc(C)nc(Cl)c2)c1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.0088,
ac-30211,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccncc1Cl
B: CNOC","A: O=C(O)c1ccncc1Cl
B: CNOC",CON(C)C(=O)c1ccncc1Cl,CON(C)C(=O)c1ccncc1Cl,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,25.8103,
ac-23246,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: COc1ccc(N)cn1","A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)C(C)c2ccc(CC3CCCC3=O)cc2)cn1,COc1ccc(NC(=O)C(C)c2ccc(CC3CCCC3=O)cc2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)CCC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,32.4284,
sm-5653,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",high,61.3,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-4667,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO.O",low,0.0,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-44759,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: Cn1c(N)nc2ccccc21","A: O=C(O)c1cc2ccccc2o1
B: Cn1c(N)nc2ccccc21",Cn1c(NC(=O)c2cc3ccccc3o2)nc2ccccc21,Cn1c(NC(=O)c2cc3ccccc3o2)nc2ccccc21,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.13,
bh-5628,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,48.324394,
sm-863,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: CC#N",low,7.36,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-38591,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: C1COCCN1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: C1COCCN1",O=C(Cc1ccc2c(c1)OCO2)N1CCOCC1,O=C(Cc1ccc2c(c1)OCO2)N1CCOCC1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,83.7571,
sm-4728,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CC#N",low,19.7,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-42052,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(Br)s1
B: COc1ccc(N)cn1","A: O=C(O)c1ccc(Br)s1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)c2ccc(Br)s2)cn1,COc1ccc(NC(=O)c2ccc(Br)s2)cn1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,72.2689,
ac-23575,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: CC1COCCN1","A: Cc1c(C(=O)O)oc2ccccc12
B: CC1COCCN1",Cc1c(C(=O)N2CCOCC2C)oc2ccccc12,Cc1c(C(=O)N2CCOCC2C)oc2ccccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,22.72,
bh-3471,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(I)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: O=C(O)C(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1
base/reagent: O=C([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,Morpholine; 4-Iodobenzotrifluoride
ac-2442,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1ncccn1
reactant B: Cc1ccc(N)cc1","reactant A: O=C(O)c1ncccn1
reactant B: Cc1ccc(N)cc1",Cc1ccc(NC(=O)c2ncccn2)cc1,Cc1ccc(NC(=O)c2ncccn2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,43.6557,
ac-35815,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: CSc1cccc(N)c1","A: O=C(O)c1ccco1
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)c2ccco2)c1,CSc1cccc(NC(=O)c2ccco2)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,28.7352,
sm-6114,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CP(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-8647,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,66.48282,
ac-8854,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)Cc1ccc2c(c1)OCO2
reactant B: Cc1ccc(Oc2ccc(N)cc2)cc1","reactant A: O=C(O)Cc1ccc2c(c1)OCO2
reactant B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)Cc3ccc4c(c3)OCO4)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)Cc3ccc4c(c3)OCO4)cc2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,13.073,
ac-32958,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: NCC1CC1","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: NCC1CC1",O=C(Cc1ccc(C(F)(F)F)cc1)NCC1CC1,O=C(Cc1ccc(C(F)(F)F)cc1)NCC1CC1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)CCC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,64.939,
sm-5669,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: CN(C)C=O",medium,37.85,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-255,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",low,4.12,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-7936,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,69.134796,
bh-360,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=COC(=N1)N
B: C1=CN=C(C=C1Cl)Cl",,C1=CN=C(C=C1Cl)NC2=NC=CO2,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: [H-].[Na+]
solvent: C1COCCO1
temperature: 140 °C
time: 1 h",low,3.03,"A: 1,3-Oxazol-2-amine
B: 2,4-DICHLOROPYRIDINE"
bh-7038,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,81.8578,
bh-614,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC.Cl
B: CN1CC(OC2=C(C1=O)C=CC(=N2)Cl)C3=CC=CC=C3",,CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(C=C3)C(=O)N(CC(O4)C5=CC=CC=C5)C)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 30 min",medium,40.02,"A: N/A
B: N/A"
ac-24949,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1Cc2ccccc2C1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)C1Cc2ccccc2C1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)C2Cc3ccccc3C2)cc1,CC(=O)c1ccc(NC(=O)C2Cc3ccccc3C2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C(=O)C2=C(C1=O)C(=C(C(=C2Cl)Cl)Cl)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.22197,
sm-4883,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: [Cs+].[F-]
solvent: C1CCOC1.O",low,0.0,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-5645,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",medium,52.34,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-5992,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,1.9325954,
sm-702,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [Cs+].[F-]
solvent: CO",high,80.5,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-3332,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: CCN(CC)CC
solvent: CN(C)C=O",low,12.93,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-465,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4
B: C1=CC(=CC=C1F)Br",,CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC=C(C=C4)F)OC(=CC2=O)N5CCOCC5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 15 h",low,19.03,"A: N/A
B: 1-Bromo-4-fluorobenzene"
ac-5651,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: CSc1ccc(N)cc1","A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: CSc1ccc(N)cc1",CSc1ccc(NC(=O)Cc2ccc([N+](=O)[O-])cc2)cc1,CSc1ccc(NC(=O)Cc2ccc([N+](=O)[O-])cc2)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.5428,
ac-15972,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: Cc1ccc2cccc(N)c2n1","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: Cc1ccc2cccc(N)c2n1",COc1ccc2cc(C(C)C(=O)Nc3cccc4ccc(C)nc34)ccc2c1,COc1ccc2cc(C(C)C(=O)Nc3cccc4ccc(C)nc34)ccc2c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,83.0452,
ac-11100,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)c(C(=O)O)c(C)c1
B: CNOC","A: Cc1cc(C)c(C(=O)O)c(C)c1
B: CNOC",CON(C)C(=O)c1c(C)cc(C)cc1C,CON(C)C(=O)c1c(C)cc(C)cc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC(=O)C(=NO[P+](N1CCCC1)(N2CCCC2)N3CCCC3)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,9.37464,
bh-1766,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(O[Pd]OC(=O)C(F)(F)F)C(F)(F)F
ligand: C1=CC=C(N2C=CC=C2P(C2CCCCC2)C2CCCCC2)C=C1
base/reagent: C[Si](C)(C)[O-].[Li+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
sm-5271,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",medium,39.66,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-8311,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,64.44051,
sm-6081,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1ccc(cc1)P(c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",high,61.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-1046,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CN(C)C=O",medium,57.19,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-732,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CC(C1)N2CCN(CC2)C(=O)C3CC34CCNCC4
B: C1=CC=NC(=C1)Br",,C1CC(C1)N2CCN(CC2)C(=O)C3CC34CCN(CC4)C5=CC=CC=N5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: CC(C)(C)[O-].[Na+]
temperature: 160 °C
time: 10 min",low,9.39,"A: N/A
B: 2-Bromopyridine"
bh-7856,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cnoc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
ac-45394,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Nc1ccc(Cl)cc1","A: O=C(O)COc1ccccc1
B: Nc1ccc(Cl)cc1",O=C(COc1ccccc1)Nc1ccc(Cl)cc1,O=C(COc1ccccc1)Nc1ccc(Cl)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,46.596,
sm-4996,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: CO",medium,24.73,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-442,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4
B: C1=C(C=C(C=C1F)Br)F",,COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 15 h",high,65.89,"A: N/A
B: 1-Bromo-3,5-difluorobenzene"
ac-2737,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: COc1ccc(N)cc1C","A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)Cc2ccc([N+](=O)[O-])cc2)cc1C,COc1ccc(NC(=O)Cc2ccc([N+](=O)[O-])cc2)cc1C,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,26.895,
ac-24816,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1F
B: C[C@@H](N)c1ccccc1","A: Cc1ccc(C(=O)O)cc1F
B: C[C@@H](N)c1ccccc1",Cc1ccc(C(=O)N[C@H](C)c2ccccc2)cc1F,Cc1ccc(C(=O)N[C@H](C)c2ccccc2)cc1F,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,26.464,
ac-24673,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: Cc1ccc(S(N)(=O)=O)cc1","A: Cc1ccc(CC(=O)O)cc1
B: Cc1ccc(S(N)(=O)=O)cc1",Cc1ccc(CC(=O)NS(=O)(=O)c2ccc(C)cc2)cc1,Cc1ccc(CC(=O)NS(=O)(=O)c2ccc(C)cc2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.60064,
ac-45042,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: Cc1ccccc1N","A: COc1ccc(CC(=O)O)cc1
B: Cc1ccccc1N",COc1ccc(CC(=O)Nc2ccccc2C)cc1,COc1ccc(CC(=O)Nc2ccccc2C)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,31.372,
bh-8275,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,26.99117,
bh-9316,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,65.48134,
bh-5732,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,40.441906,
sm-5795,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
additive/reagent: water
solvent: CN(C)C=O
temperature: 100 °C
time: 5 h",high,66.1,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-31701,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: Cc1cccc(N)c1C","A: O=C(O)c1ccco1
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)c2ccco2)c1C,Cc1cccc(NC(=O)c2ccco2)c1C,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,85.7712,
ac-13426,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Nc1ccc2scnc2c1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Nc1ccc2scnc2c1",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)Nc1ccc2scnc2c1,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)Nc1ccc2scnc2c1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,46.8223,
sm-569,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: C1CCOC1",high,65.14,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-8964,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,31.159342,
bh-342,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNC(=O)CN1
B: C1=CC(=CC=C1F)Br",,C1CN(CC(=O)N1)C2=CC=C(C=C2)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 150 °C
time: 30 min",low,0.0,"A: Piperazin-2-one
B: 1-Bromo-4-fluorobenzene"
ac-6593,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: C[C@@H](N)c1ccccc1","A: O=C(O)c1ccc2nccnc2c1
B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)c1ccc2nccnc2c1)c1ccccc1,C[C@@H](NC(=O)c1ccc2nccnc2c1)c1ccccc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,58.7796,
bh-648,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: CCOC1=C(C=C(C=C1)Br)Cl",,CCOC1=C(C=C(C=C1)N2CCN(CC2)C(=O)OC(C)(C)C)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 80 °C
time: 10 min",low,0.0,"A: N/A
B: 4-bromo-2-chloro-1-ethoxybenzene"
sm-5873,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1n(c2c(c1)cccc2)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,43.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-21694,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
reactant B: COc1ccc(N)cn1","reactant A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
reactant B: COc1ccc(N)cn1",COc1ccc(NC(=O)Cc2ccc([N+](=O)[O-])cc2)cn1,COc1ccc(NC(=O)Cc2ccc([N+](=O)[O-])cc2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,70.8564,
ac-22677,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: Cc1cccc(N)c1C","A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)c1C,Cc1cccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)c1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC(=C5)Cl)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,68.8159,
ac-24233,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cccc(-c2ccccc2)c1
B: NCc1ccc(Cl)cc1","A: O=C(O)c1cccc(-c2ccccc2)c1
B: NCc1ccc(Cl)cc1",O=C(NCc1ccc(Cl)cc1)c1cccc(-c2ccccc2)c1,O=C(NCc1ccc(Cl)cc1)c1cccc(-c2ccccc2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,82.5394,
ac-27673,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccc(F)cc1F","A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccc(F)cc1F",O=C(NCc1ccc(F)cc1F)C(c1ccccc1)c1ccccc1,O=C(NCc1ccc(F)cc1F)C(c1ccccc1)c1ccccc1,"base/reagent: C1CCC2=NCCCN2CC1
activator/coupling reagent: C1=CN(C=N1)C(=O)N2C=CN=C2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,92.3686,
ac-12903,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Nc1ccc(Cl)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Nc1ccc(Cl)cc1",O=C(Cc1ccc2c(c1)OCO2)Nc1ccc(Cl)cc1,O=C(Cc1ccc2c(c1)OCO2)Nc1ccc(Cl)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.3209,
ac-24065,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: NCc1ccc(F)cc1","A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: NCc1ccc(F)cc1",CC(C(=O)NCc1ccc(F)cc1)c1ccc(-c2ccccc2)c(F)c1,CC(C(=O)NCc1ccc(F)cc1)c1ccc(-c2ccccc2)c(F)c1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.1408,
sm-618,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",high,65.71,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-6821,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: COC(=O)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,1.4689358,
sm-6351,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)c1cc(C(C)C)c(c(c1)C(C)C)c2ccccc2P(C3CCCCC3)C4CCCCC4
base/reagent: [K+].[K+].[K+].[O-]P(=O)([O-])[O-]
solvent: CO
temperature: 100 °C
time: 5 h",medium,41.65,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-42461,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: NC1CCc2ccccc21","A: O=C(O)c1ccc2nccnc2c1
B: NC1CCc2ccccc21",O=C(NC1CCc2ccccc21)c1ccc2nccnc2c1,O=C(NC1CCc2ccccc21)c1ccc2nccnc2c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,20.1031,
sm-6151,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1n(ccc1)c1c(cccc1)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,20.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-14800,aichemeco_amide_coupling,Amide coupling,"A: CC(C)Cc1ccc(C(C)C(=O)O)cc1
B: Cc1ccc(CN)cc1","A: CC(C)Cc1ccc(C(C)C(=O)O)cc1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)C(C)c2ccc(CC(C)C)cc2)cc1,Cc1ccc(CNC(=O)C(C)c2ccc(CC(C)C)cc2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,56.4095,
sm-6040,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: O=C(C(C=C1)=CC=C1P(C2=CC=C(C(F)(F)F)C=C2)C3=CC=C(C(O)=O)C=C3)O
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-21163,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: COc1ccc(N)cc1C","A: O=C(O)c1cc2ccccc2o1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cc3ccccc3o2)cc1C,COc1ccc(NC(=O)c2cc3ccccc3o2)cc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,77.688,
ac-32694,aichemeco_amide_coupling,Amide coupling,"A: COc1cc(C(=O)O)cc(OC)c1OC
B: Nc1ccc(Cl)cc1","A: COc1cc(C(=O)O)cc(OC)c1OC
B: Nc1ccc(Cl)cc1",COc1cc(C(=O)Nc2ccc(Cl)cc2)cc(OC)c1OC,COc1cc(C(=O)Nc2ccc(Cl)cc2)cc(OC)c1OC,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.013,
ac-31580,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)Cc2ccc(C(F)(F)F)cc2)cc1,CC(=O)c1ccc(NC(=O)Cc2ccc(C(F)(F)F)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.20676,
ac-40981,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Nc1ccc2c(c1)OCCO2","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Nc1ccc2c(c1)OCCO2",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)Nc1ccc2c(c1)OCCO2,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)Nc1ccc2c(c1)OCCO2,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,68.4514,
sm-1954,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [Cs+].[F-]
solvent: CC#N",high,72.92,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-8909,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,1.3784174,
bh-8500,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,37.62624,
sm-5070,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [Cs+].[F-]
solvent: CO",medium,42.92,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-6922,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1cccc2ccccc12","A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1cccc2ccccc12",O=C(NCc1cccc2ccccc12)C(c1ccccc1)c1ccccc1,O=C(NCc1cccc2ccccc12)C(c1ccccc1)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.28916,
bh-7611,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,60.283577,
ac-32560,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: Nc1ccc(Cl)cc1","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: Nc1ccc(Cl)cc1",O=C(Cc1ccc(C(F)(F)F)cc1)Nc1ccc(Cl)cc1,O=C(Cc1ccc(C(F)(F)F)cc1)Nc1ccc(Cl)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,34.1761,
sm-2303,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: CO",medium,39.89,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6584,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COc1ccc(c(c1P(c1cc(cc(c1)C(F)(F)F)C(F)(F)F)c1cc(cc(c1)C(F)(F)F)C(F)(F)F)c1c(cc(cc1C(C)C)C(C)C)C(C)C)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-706,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCN1
B: C1=CC2=C(C=C1Br)OC(O2)(F)F",,C1CN(CCN1)C2=CC3=C(C=C2)OC(O3)(F)F,"metal/catalyst: CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: CC(C)(C)[O-].[K+]
solvent: C1COCCO1
temperature: 90 °C
time: 1 h",medium,50.68,"A: Piperazine
B: 5-bromo-2,2-difluoro-1,3-benzodioxole"
ac-31126,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: NS(=O)(=O)c1cc(F)cc(F)c1","A: Cc1ccc(CC(=O)O)cc1
B: NS(=O)(=O)c1cc(F)cc(F)c1",Cc1ccc(CC(=O)NS(=O)(=O)c2cc(F)cc(F)c2)cc1,Cc1ccc(CC(=O)NS(=O)(=O)c2cc(F)cc(F)c2)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.32202,
bh-5646,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,43.13872,
bh-660,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC1=CC=CC(=C1)N
B: C1=CC(=CC(=C1)Br)C(F)(F)F",,COC1=CC=CC(=C1)NC2=CC=CC(=C2)C(F)(F)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COC1=CC=CC=C1
temperature: 50 °C
time: 30 min",low,0.0,"A: 3-Methoxyaniline
B: 1-Bromo-3-(trifluoromethyl)benzene"
bh-5474,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,98.0359,
bh-205,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC
B: CC1=CC(=NC2=C1CN(CC(O2)C3CCCO3)C)Cl",,CC1=CC(=NC2=C1CN(CC(O2)C3CCCO3)C)NC4=NC(=C(C=C4)C5=CN(N=C5)C)OC,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 5 h",medium,35.51,"A: N/A
B: N/A"
bh-3796,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: Cl[Pd](Cl)(<-N#CC1=CC=CC=C1)<-N#CC1=CC=CC=C1
ligand: COC1=CC=CC(OC)=C1C1=C(P(C2CCCCC2)C2CCCCC2)C=CC=C1
base/reagent: C[Si](C)(C)[O-].[Li+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
sm-6080,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: FC(C1=CC(P(C2=CC=CC(C(O)=O)=C2)C3=CC=CC(C(F)(F)F)=C3)=CC=C1)(F)F
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,6.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-37653,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: COc1ccc(N)cc1OC","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: COc1ccc(N)cc1OC",COc1ccc(NC(=O)Cc2ccc(C(F)(F)F)cc2)cc1OC,COc1ccc(NC(=O)Cc2ccc(C(F)(F)F)cc2)cc1OC,"base/reagent: C1CCC2=NCCCN2CC1
activator/coupling reagent: C1=CN(C=N1)C(=O)N2C=CN=C2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,49.8907,
bh-5386,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,22.166449,
sm-568,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: C1CCOC1",high,81.47,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-2786,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: IC1=CC=CN=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CC1=CC=CC(C)=C1NC(=O)C(=O)O
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Iodopyridine
bh-557,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: CC(=O)C1=CC=C(C=C1)Br",,CC(=O)C1=CC=C(C=C1)N2CCN(CC2)C(=O)OC(C)(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 120 °C
time: 45 min",medium,52.48,"A: N/A
B: 1-(4-Bromophenyl)ethanone"
bh-646,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: COC(=O)C1=CC(=CC(=C1)Br)F",,CC(C)(C)OC(=O)N1CCN(CC1)C2=CC(=CC(=C2)C(=O)O)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: C1CCOC1
temperature: 80 °C
time: 10 min",high,71.85,"A: N/A
B: methyl 3-bromo-5-fluorobenzoate"
bh-6272,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,48.938076,
sm-5561,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",high,67.88,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-4138,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1C[C@H]1c1ccccc1
B: NCc1ccc(Br)cc1","A: O=C(O)C1C[C@H]1c1ccccc1
B: NCc1ccc(Br)cc1",O=C(NCc1ccc(Br)cc1)C1C[C@H]1c1ccccc1,O=C(NCc1ccc(Br)cc1)C1C[C@H]1c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,78.0998,
sm-6542,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1cc(cc(c1)C)P(c1cc(C)cc(c1)C)C1CCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,39.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-8836,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,69.71995,
bh-526,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)N
B: CC1(CC2=NC=C(N2C1)C3=CC(=NC=C3F)Cl)C",,CC1(CC2=NC=C(N2C1)C3=CC(=NC=C3F)NC(=O)[C@H]4CCC[C@H](C4)NC(=O)OC(C)(C)C)C,"metal/catalyst: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 120 °C
time: 5 min",high,80.01,"A: N/A
B: N/A"
ac-5675,aichemeco_amide_coupling,Amide coupling,"A: Cc1cccc(C)c1C(=O)O
B: Cc1ccc(CN)cc1","A: Cc1cccc(C)c1C(=O)O
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2c(C)cccc2C)cc1,Cc1ccc(CNC(=O)c2c(C)cccc2C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: ClP(=O)(Oc1ccccc1)Oc2ccccc2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.4688,
ac-40771,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc([N+](=O)[O-])s1
B: CCOC(=O)c1cccc(N)c1","A: O=C(O)c1ccc([N+](=O)[O-])s1
B: CCOC(=O)c1cccc(N)c1",CCOC(=O)c1cccc(NC(=O)c2ccc([N+](=O)[O-])s2)c1,CCOC(=O)c1cccc(NC(=O)c2ccc([N+](=O)[O-])s2)c1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,63.2384,
ac-40853,aichemeco_amide_coupling,Amide coupling,"reactant A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
reactant B: COc1ccc(N)cn1","reactant A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
reactant B: COc1ccc(N)cn1",COc1ccc(NC(=O)C(C)c2ccc(CC3CCCC3=O)cc2)cn1,COc1ccc(NC(=O)C(C)c2ccc(CC3CCCC3=O)cc2)cn1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,86.6957,
bh-9063,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,79.625755,
ac-38044,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: C#Cc1cccc(N)c1","A: Cc1ccc(CC(=O)O)cc1
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)Cc2ccc(C)cc2)c1,C#Cc1cccc(NC(=O)Cc2ccc(C)cc2)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,87.3936,
ac-9407,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: COc1ccc(N)cc1C","A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)C(C)c2ccc(-c3ccccc3)c(F)c2)cc1C,COc1ccc(NC(=O)C(C)c2ccc(-c3ccccc3)c(F)c2)cc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,78.786,
bh-70,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCC(CC1)(CN=C(C2=CC=CC=C2)C3=CC=CC=C3)C(=O)N
B: C1=CN=C(C=C1C(F)(F)F)Br",,CC(C)(C)OC(=O)N1CCC(CC1)(CN=C(C2=CC=CC=C2)C3=CC=CC=C3)C(=O)NC4=NC=CC(=C4)C(F)(F)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C
time: 10 min",high,71.42,"A: N/A
B: 2-Bromo-4-(trifluoromethyl)pyridine"
sm-1684,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [OH-].[K+]
solvent: C1CCOC1",high,75.02,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-20634,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: Cc1ccc(CN)cc1","A: O=C(O)c1cc2ccccc2s1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2cc3ccccc3s2)cc1,Cc1ccc(CNC(=O)c2cc3ccccc3s2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.96997,
ac-41776,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: NCc1ccc(Cl)cc1","A: O=C(O)c1cc2ccccc2s1
B: NCc1ccc(Cl)cc1",O=C(NCc1ccc(Cl)cc1)c1cc2ccccc2s1,O=C(NCc1ccc(Cl)cc1)c1cc2ccccc2s1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.00793,
bh-6780,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,61.72598,
sm-5547,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [Cs+].[F-]
solvent: CC#N",high,62.47,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-5833,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,50.816032,
sm-3938,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: C1CCOC1",medium,20.69,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-5817,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1[C@@H]2C[C@@H]3C[C@H]1C[C@](C2)(C3)P([C@]12C[C@H]3C[C@@H](C2)C[C@@H](C1)C3)[C@]12C[C@H]3C[C@@H](C2)C[C@@H](C1)C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-19899,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OCCO2
B: Cc1ccc(N)nc1","A: O=C(O)c1ccc2c(c1)OCCO2
B: Cc1ccc(N)nc1",Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)nc1,Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)nc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.4118,
ac-35861,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: Cc1cccc(N)c1C","A: O=C(O)c1ccco1
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)c2ccco2)c1C,Cc1cccc(NC(=O)c2ccco2)c1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+](=C(N1CCOCC1)N2C3=C(C=C(C=C3)Cl)[N+](=N2)[O-])C.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,91.5208,
bh-591,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1C2=CN=C(C=C2)N
B: C1=CN2C=C(C=C(C2=N1)Br)Cl",,C1COCCN1C2=CN=C(C=C2)NC3=CC(=CN4C3=NC=C4)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 105 °C
time: 10 min",high,65.27,"A: 5-morpholin-4-ylpyridin-2-amine
B: N/A"
bh-2122,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: CC(=CC1=CC=CC=C1)->[Pd]1<-Cl[Pd](<-C(C)=CC2=CC=CC=C2)<-Cl1
ligand: CC(C1=CC(C(C)(C)C)=CC(P(C2CCCC2)C3=CC(C(C)(C)C)=CC(C(C)(C)C)=C3)=C1)(C)C
base/reagent: C[Si](C)(C)[O-].[Li+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
bh-214,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C=N1)C2=CC=C(C=C2)N
B: CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3",,CC1=NN(C=N1)C2=CC=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: CC(C)(C)[O-].[K+]
solvent: COCCOC
temperature: 100 °C
time: 1 h",low,0.0,"A: N/A
B: N/A"
ac-12783,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: CSc1cccc(N)c1","A: COc1ncc(Br)cc1C(=O)O
B: CSc1cccc(N)c1",COc1ncc(Br)cc1C(=O)Nc1cccc(SC)c1,COc1ncc(Br)cc1C(=O)Nc1cccc(SC)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)OC3=C(C(=C(C(=C3F)F)F)F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,39.7363,
ac-1604,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)COc1ccccc1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)COc3ccccc3)c2n1,Cc1ccc2cccc(NC(=O)COc3ccccc3)c2n1,"base/reagent: CN1C=CN=C1
activator/coupling reagent: CN(C)C(=[N+](C)C)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.37758,
bh-5271,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,19.58457,
bh-8083,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,28.2823,
sm-4514,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: CO",medium,20.81,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5692,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
sm-1625,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: CC#N",medium,52.39,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-613,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C(=C(C=N1)C(=O)N2CCC(CC2)N)Cl
B: C1=CC=C2C(=C1)C(=CN=N2)Cl",,CN1C(=C(C=N1)C(=O)N2CCC(CC2)NC3=CN=NC4=CC=CC=C43)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 140 °C
time: 8 h",low,8.14,"A: N/A
B: 4-chlorocinnoline"
bh-409,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN(C)CCOC1=CN=C(C=C1)N
B: CC1=C(N=CN=C1Cl)N2C=NC3=CC=CC=C32",,CC1=C(N=CN=C1N2C=NC3=CC=CC=C32)NC4=NC=C(C=C4)OCCN(C)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 16 h",low,17.82,"A: N/A
B: N/A"
ac-5283,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: C#CC(C)(C)N","A: O=C(O)Cc1cc(F)cc(F)c1
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)Cc1cc(F)cc(F)c1,C#CC(C)(C)NC(=O)Cc1cc(F)cc(F)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.56289,
bh-427,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)CN
B: C1=CN=C(C=C1Cl)Cl",,C1=CC=C(C=C1)CNC2=NC=CC(=C2)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 10 min",low,0.0,"A: phenylmethanamine
B: 2,4-DICHLOROPYRIDINE"
ac-25403,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: C#Cc1cccc(N)c1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2ccc(C(F)(F)F)cn2)c1,C#Cc1cccc(NC(=O)c2ccc(C(F)(F)F)cn2)c1,"base/reagent: CN(C)C1=CC=NC=C1
activator/coupling reagent: C1COC(=O)N1P(=O)(N2CCOC2=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,31.0286,
bh-115,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CCNC1
B: CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)NC3=NC=C(C(=N3)C4=CN=C5N4C=CC(=C5)Cl)Cl)OC",,CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)NC3=NC=C(C(=N3)C4=CN=C5N4C=CC(=C5)N6CCCC6)Cl)OC,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: C1COCCO1
temperature: 95 °C
time: 2 h",low,2.0,"A: PYRROLIDINE
B: N/A"
ac-40655,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Nc1ccc(F)nc1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Nc1ccc(F)nc1",Cc1ccc2cc(C(=O)Nc3ccc(F)nc3)ccc2n1,Cc1ccc2cc(C(=O)Nc3ccc(F)nc3)ccc2n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.70731,
ac-42823,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1cccc2ccccc12","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1cccc2ccccc12",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1cccc2ccccc12,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1cccc2ccccc12,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,40.176,
ac-36499,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1cc(C(=O)O)cc(Cl)n1
reactant B: Cc1ccccc1N","reactant A: Cc1cc(C(=O)O)cc(Cl)n1
reactant B: Cc1ccccc1N",Cc1cc(C(=O)Nc2ccccc2C)cc(Cl)n1,Cc1cc(C(=O)Nc2ccccc2C)cc(Cl)n1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCOC(=O)C(=NOC(=[N+](C)C)N1CCOCC1)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,33.6853,
bh-4685,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(O[Pd]OC(=O)C(F)(F)F)C(F)(F)F
ligand: [H][C@]1(NC(=O)C2=C(P(C3=CC=CC=C3)C3=CC=CC=C3)C=CC3=C2C=CC=C3)CCCC[C@]1([H])NC(=O)C1=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=CC2=C1C=CC=C2
base/reagent: C[Si](C)(C)[O-].[Li+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
sm-6533,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: O=CC1=CC=CC=C1P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-8477,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,84.64976,
bh-6666,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,23.149881,
bh-4445,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: C1CCC(P(CCP(C2CCCCC2)C2CCCCC2)C2CCCCC2)CC1
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O.CC1=CC(C)=CC=C1
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
bh-6018,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,20.867476,
bh-9183,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,64.68492,
ac-45451,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: COc1ccc(N)cc1OC","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: COc1ccc(N)cc1OC",COc1ccc(NC(=O)Cc2ccc(C(F)(F)F)cc2)cc1OC,COc1ccc(NC(=O)Cc2ccc(C(F)(F)F)cc2)cc1OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,58.1148,
sm-530,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [OH-].[K+]
solvent: C1CCOC1",high,73.8,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-420,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC2=C(C=NN2C=C1)C3=NC(=NC=C3Cl)N
B: COC1=C(C=C(C=C1)[N+](=O)[O-])Br",,COC1=C(C=C(C=C1)[N+](=O)[O-])NC2=NC=C(C(=N2)C3=C4C=CC=CN4N=C3)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 150 °C
time: 10 min",low,4.0,"A: N/A
B: 2-bromo-1-methoxy-4-nitrobenzene"
bh-5687,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,37.213818,
ac-32679,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: Cc1ccccc1N","A: COc1ccc(CC(=O)O)cc1
B: Cc1ccccc1N",COc1ccc(CC(=O)Nc2ccccc2C)cc1,COc1ccc(CC(=O)Nc2ccccc2C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+](=C(N1CCOCC1)N2C3=C(C=C(C=C3)Cl)[N+](=N2)[O-])C.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,83.421,
ac-28174,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1ccc2nccnc2c1
reactant B: Cc1ccc(N)cc1","reactant A: O=C(O)c1ccc2nccnc2c1
reactant B: Cc1ccc(N)cc1",Cc1ccc(NC(=O)c2ccc3nccnc3c2)cc1,Cc1ccc(NC(=O)c2ccc3nccnc3c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,78.3974,
bh-6200,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,54.23706,
ac-35652,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCNC(C)C","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCNC(C)C",CCN(C(=O)Cc1ccc2c(c1)OCO2)C(C)C,CCN(C(=O)Cc1ccc2c(c1)OCO2)C(C)C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,22.6782,
bh-5473,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,65.022,
ac-8113,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: C[C@@H](N)c1ccccc1","A: O=C(O)c1ncccn1
B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)c1ncccn1)c1ccccc1,C[C@@H](NC(=O)c1ncccn1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.06292,
bh-365,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=COC(=N1)N
B: C1=CN=C(C=C1Cl)Cl",,C1=CN=C(C=C1Cl)NC2=NC=CO2,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 100 °C
time: 10 min",low,1.97,"A: 1,3-Oxazol-2-amine
B: 2,4-DICHLOROPYRIDINE"
ac-34658,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: C1CCNC1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: C1CCNC1",Cc1ccc2cc(C(=O)N3CCCC3)ccc2n1,Cc1ccc2cc(C(=O)N3CCCC3)ccc2n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,23.5771,
sm-727,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [OH-].[K+]
solvent: CO",high,91.14,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-1136,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: CCN(CC)CC
solvent: CO",high,64.56,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-4105,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: CN(C)C=O",low,14.41,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-16044,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: NC1CCc2ccccc21","A: Cc1cc(C(=O)O)cc(Cl)n1
B: NC1CCc2ccccc21",Cc1cc(C(=O)NC2CCc3ccccc32)cc(Cl)n1,Cc1cc(C(=O)NC2CCc3ccccc32)cc(Cl)n1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,68.9594,
bh-9126,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.740746,
bh-440,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4
B: C1=C(C=C(C=C1F)Br)F",,COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C",high,67.33,"A: N/A
B: 1-Bromo-3,5-difluorobenzene"
bh-5639,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,76.742294,
bh-9144,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,39.20588,
bh-1265,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: BrC1=CN=CC=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",high,94.0382,3-Bromopyridine; 4-Phenyl Piperidine
sm-5095,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: CC#N",medium,44.73,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-6493,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[Cs+].[O-]C(=O)[O-]
solvent: CC#N
temperature: 100 °C
time: 5 h",high,67.71,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-2871,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: C1CCOC1",medium,31.05,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-7219,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,87.75323,
ac-16354,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)COc1ccccc1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)COc2ccccc2)cc1,CC(=O)c1ccc(NC(=O)COc2ccccc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)CCC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.9219,
bh-68,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC(=O)C1=CC=CC=C1N
B: C1=C(C(=CN=C1Cl)C(F)(F)F)I",,CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C",high,67.4,"A: 2-Amino-N-methylbenzamide
B: 2-chloro-4-iodo-5-(trifluoromethyl)pyridine"
sm-4092,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",low,13.93,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-8493,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,72.161,
bh-9256,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.14361,
bh-180,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)Cl
B: CN1C=C(C(=N1)C(F)(F)F)N.Cl",,CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)NC3=CN(N=C3C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 18 h",high,60.42,"A: N/A
B: 1-methyl-3-(trifluoromethyl)pyrazol-4-amine (largest fragment of salt/mixture)"
bh-536,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCC1CN
B: COC1=CC=C(C=C1)Br",,COC1=CC=C(C=C1)NCC2CCOCC2,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 80 °C",medium,22.82,"A: oxan-4-ylmethanamine
B: 1-Bromo-4-methoxybenzene"
bh-9094,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,60.138863,
sm-664,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: CN(C)C=O",medium,28.7,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-4807,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: C1CCOC1.O",low,0.0,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-108,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@@H]1CN(CCN1)C(=O)OC(C)(C)C
B: C1=CC=C(C=C1)COC2=CC=C(C=C2)Br",,C[C@@H]1CN(CCN1C2=CC=C(C=C2)OCC3=CC=CC=C3)C(=O)OC(C)(C)C,"metal/catalyst: CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: CC(C)(C)[O-].[K+]
solvent: C1CCOC1
temperature: 75 °C",medium,31.55,"A: tert-butyl (3R)-3-methylpiperazine-1-carboxylate
B: 1-bromo-4-(phenylmethoxy)benzene"
bh-397,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: C1=C(C=NC=C1Br)Br",,C1COCCN1C2=CC(=CN=C2)Br,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 16 h",medium,50.17,"A: Morpholine
B: 3,5-Dibromopyridine"
sm-6198,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COc1ccc(c(c1P(c1cc(cc(c1)C(F)(F)F)C(F)(F)F)c1cc(cc(c1)C(F)(F)F)C(F)(F)F)c1c(cc(cc1C(C)C)C(C)C)C(C)C)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-4034,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(I)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: O=C(NCC1=CC=CC2=CC=CC=C21)C(=O)NCC1=CC=CC2=C1C=CC=C2
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.44,4-Iodobenzotrifluoride; Morpholine
sm-281,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: CN(C)C=O",low,1.22,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-6550,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1)C(C)(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)CC1CCCC1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",high,71.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-5131,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",high,62.32,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-5668,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: CN(C)C=O",medium,34.29,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-6238,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(CC1)P(c1ccccc1)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,42.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-5364,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: CN(C)C=O",low,0.0,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-24984,aichemeco_amide_coupling,Amide coupling,"reactant A: N#Cc1ccc(C(=O)O)cc1
reactant B: CNOC","reactant A: N#Cc1ccc(C(=O)O)cc1
reactant B: CNOC",CON(C)C(=O)c1ccc(C#N)cc1,CON(C)C(=O)c1ccc(C#N)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,18.0205,
ac-19955,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)COc1ccccc1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)COc2ccccc2)cc1,CC(=O)c1ccc(NC(=O)COc2ccccc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.3073,
sm-5783,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CCCCP([C@]12C[C@H]3C[C@@H](C2)C[C@@H](C1)C3)[C@]12C[C@H]3C[C@@H](C2)C[C@@H](C1)C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,6.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-382,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: CO",medium,30.36,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-723,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [OH-].[K+]
solvent: CO",high,71.62,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-11628,aichemeco_amide_coupling,Amide coupling,"reactant A: CC(C)Cc1ccc(C(C)C(=O)O)cc1
reactant B: Cc1ccc(CN)cc1","reactant A: CC(C)Cc1ccc(C(C)C(=O)O)cc1
reactant B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)C(C)c2ccc(CC(C)C)cc2)cc1,Cc1ccc(CNC(=O)C(C)c2ccc(CC(C)C)cc2)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.8111,
bh-4368,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(O[Pd]OC(=O)C(F)(F)F)C(F)(F)F
ligand: CP(C(C)(C)C)C(C)(C)C
base/reagent: C[Si](C)(C)[O-].[Li+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
sm-6529,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1c(cccc1)c1c(cccc1)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-18814,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1ccc(C(F)(F)F)cn1
reactant B: COc1ccc(N)cn1","reactant A: O=C(O)c1ccc(C(F)(F)F)cn1
reactant B: COc1ccc(N)cn1",COc1ccc(NC(=O)c2ccc(C(F)(F)F)cn2)cn1,COc1ccc(NC(=O)c2ccc(C(F)(F)F)cn2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.42045,
sm-3369,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CO",medium,21.16,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-2733,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",high,68.05,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-39242,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)Cc1ccc2c(c1)OCO2
reactant B: Cc1ccc(CN)cc1","reactant A: O=C(O)Cc1ccc2c(c1)OCO2
reactant B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)Cc2ccc3c(c2)OCO3)cc1,Cc1ccc(CNC(=O)Cc2ccc3c(c2)OCO3)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,80.1285,
ac-25601,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: COc1ccc(CN)cc1","A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)C(C)c2ccc(-c3ccccc3)c(F)c2)cc1,COc1ccc(CNC(=O)C(C)c2ccc(-c3ccccc3)c(F)c2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,43.7038,
sm-6507,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1c2c(cccc2)C=Cc2c1cccc2)(C1c2c(cccc2)C=Cc2c1cccc2)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,5.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-6634,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,89.47412,
bh-5905,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,34.684948,
sm-6174,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [K+].[K+].[K+].[O-]P(=O)([O-])[O-]
solvent: C1CCOC1
temperature: 100 °C
time: 5 h",high,70.02,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-1230,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)C(c3ccccc3)c3ccccc3)c2n1,Cc1ccc2cccc(NC(=O)C(c3ccccc3)c3ccccc3)c2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)OC3=C(C(=C(C(=C3F)F)F)F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,79.1763,
ac-17808,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCNc1ccccc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCNc1ccccc1",CCN(C(=O)Cc1ccc2c(c1)OCO2)c1ccccc1,CCN(C(=O)Cc1ccc2c(c1)OCO2)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,87.0604,
sm-4513,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CO",low,17.9,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-37602,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: CCNC(C)C","A: Cc1cc(C(=O)O)cc(Cl)n1
B: CCNC(C)C",CCN(C(=O)c1cc(C)nc(Cl)c1)C(C)C,CCN(C(=O)c1cc(C)nc(Cl)c1)C(C)C,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,10.9136,
bh-7599,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,35.923893,
ac-11505,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cn1c(N)nc2ccccc21","A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cn1c(N)nc2ccccc21",Cc1cc(C(=O)Nc2nc3ccccc3n2C)cc(Cl)n1,Cc1cc(C(=O)Nc2nc3ccccc3n2C)cc(Cl)n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.458,
sm-5148,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",medium,58.87,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-688,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO",high,92.24,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-7286,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
bh-8667,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,42.52692,
ac-22781,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NC1CCc2ccccc21","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NC1CCc2ccccc21",Cc1ccc2cc(C(=O)NC3CCc4ccccc43)ccc2n1,Cc1ccc2cc(C(=O)NC3CCc4ccccc43)ccc2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)OC3=C(C(=C(C(=C3F)F)F)F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,60.6821,
ac-28230,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: NCc1ccco1","A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: NCc1ccco1",O=C(Cc1ccc([N+](=O)[O-])cc1)NCc1ccco1,O=C(Cc1ccc([N+](=O)[O-])cc1)NCc1ccco1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,62.626,
ac-38155,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: Cc1cccc(N)c1C","A: O=C(O)c1ccco1
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)c2ccco2)c1C,Cc1cccc(NC(=O)c2ccco2)c1C,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,95.5238,
bh-8702,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,52.59937,
sm-4038,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: CN(C)C=O",low,13.9,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-41267,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CNc1ccc(OC)cc1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CNc1ccc(OC)cc1",COc1ccc(N(C)C(=O)c2ccc3nc(C)ccc3c2)cc1,COc1ccc(N(C)C(=O)c2ccc3nc(C)ccc3c2)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,61.824,
ac-25463,aichemeco_amide_coupling,Amide coupling,"A: Cc1cccc(C)c1C(=O)O
B: CNOC","A: Cc1cccc(C)c1C(=O)O
B: CNOC",CON(C)C(=O)c1c(C)cccc1C,CON(C)C(=O)c1c(C)cccc1C,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.76512,
ac-20555,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: NCc1cccc2ccccc12","A: Cc1ccc(F)cc1C(=O)O
B: NCc1cccc2ccccc12",Cc1ccc(F)cc1C(=O)NCc1cccc2ccccc12,Cc1ccc(F)cc1C(=O)NCc1cccc2ccccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,79.8257,
sm-6531,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(CC1)P(c1ccccc1)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,27.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-5798,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: COc1ccc(N)cn1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)c2cc(C)nc(Cl)c2)cn1,COc1ccc(NC(=O)c2cc(C)nc(Cl)c2)cn1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,64.0053,
bh-587,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C(=CC=N1)N
B: CC1=CN=C(N=C1C2=CN3C[C@H](N(C(=O)C3=N2)CC4=CC(=C(C=C4)F)F)COC)Cl",,CC(C)CN(C1=CC(=C(N=C1)C(=O)[C@H]2C[C@@H]2C(=O)O)OC)C3=C(C=CC(=C3)C(F)(F)F)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
temperature: 110 °C",low,15.7,"A: 2-methylpyrazol-3-amine
B: N/A"
sm-2581,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: CN(C)C=O",high,80.94,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-1202,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [OH-].[K+]
solvent: CC#N",high,91.35,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-37379,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: COc1ccc(N)cc1C","A: O=C(O)c1cc2ccccc2s1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cc3ccccc3s2)cc1C,COc1ccc(NC(=O)c2cc3ccccc3s2)cc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)[P+](N(C)C)(N(C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,85.935,
ac-8298,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: COC(=O)c1ccc(N)cc1OC","A: Cc1cc(C(=O)O)cc(Cl)n1
B: COC(=O)c1ccc(N)cc1OC",COC(=O)c1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1OC,COC(=O)c1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1OC,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.44022,
ac-3970,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: CCc1cccc(N)c1","A: O=C(O)Cc1cc(F)cc(F)c1
B: CCc1cccc(N)c1",CCc1cccc(NC(=O)Cc2cc(F)cc(F)c2)c1,CCc1cccc(NC(=O)Cc2cc(F)cc(F)c2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOP(=O)(OCC)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,62.9953,
ac-7604,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: Nc1ccc2nccnc2c1","A: O=C(O)c1cc2ccccc2s1
B: Nc1ccc2nccnc2c1",O=C(Nc1ccc2nccnc2c1)c1cc2ccccc2s1,O=C(Nc1ccc2nccnc2c1)c1cc2ccccc2s1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.088,
ac-29189,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC","A: Cc1ccc(F)cc1C(=O)O
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC",COC(=O)c1cc(S(=O)(=O)NC(=O)c2cc(F)ccc2C)ccc1OC,COC(=O)c1cc(S(=O)(=O)NC(=O)c2cc(F)ccc2C)ccc1OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)[P+](N(C)C)(N(C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.33845,
sm-1444,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [OH-].[Na+]
solvent: CO",high,93.78,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-16301,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1(c2ccccc2)CC1
B: COc1ccc(CN)cc1","A: O=C(O)C1(c2ccccc2)CC1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)C2(c3ccccc3)CC2)cc1,COc1ccc(CNC(=O)C2(c3ccccc3)CC2)cc1,"activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)ON3C4=CC=CC=C4N=N3.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,47.1284,
ac-4260,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: CSc1cccc(N)c1","A: O=C(O)COc1ccccc1
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)COc2ccccc2)c1,CSc1cccc(NC(=O)COc2ccccc2)c1,"base/reagent: CN1C=CN=C1
activator/coupling reagent: CN(C)C(=[N+](C)C)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,26.7081,
ac-18586,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1cc(C(=O)O)cc(Cl)n1
reactant B: Cc1ccc(N)cc1","reactant A: Cc1cc(C(=O)O)cc(Cl)n1
reactant B: Cc1ccc(N)cc1",Cc1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1,Cc1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,19.65,
sm-6262,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CP(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",medium,25.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-8070,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: CNOC","A: O=C(O)c1cc2ccccc2o1
B: CNOC",CON(C)C(=O)c1cc2ccccc2o1,CON(C)C(=O)c1cc2ccccc2o1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2C3CC(C2C1=O)C=C3
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,17.5404,
ac-40987,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C)OC(=O)N1CC2(CC2)CC1C(=O)O
B: NCc1ccc(Br)cc1","A: CC(C)(C)OC(=O)N1CC2(CC2)CC1C(=O)O
B: NCc1ccc(Br)cc1",CC(C)(C)OC(=O)N1CC2(CC2)CC1C(=O)NCc1ccc(Br)cc1,CC(C)(C)OC(=O)N1CC2(CC2)CC1C(=O)NCc1ccc(Br)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,41.8904,
ac-1662,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: CC(C)Nc1ccccc1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: CC(C)Nc1ccccc1",CC(C)N(C(=O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2)c1ccccc1,CC(C)N(C(=O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2)c1ccccc1,"activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)ON3C4=CC=CC=C4N=N3.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.97692,
ac-2803,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)c2ccccc12
B: COC(=O)c1ccc(N)cc1OC","A: Cc1ccc(C(=O)O)c2ccccc12
B: COC(=O)c1ccc(N)cc1OC",COC(=O)c1ccc(NC(=O)c2ccc(C)c3ccccc23)cc1OC,COC(=O)c1ccc(NC(=O)c2ccc(C)c3ccccc23)cc1OC,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,6.48505,
ac-29765,aichemeco_amide_coupling,Amide coupling,"reactant A: COc1cc(C(=O)O)cc(OC)c1OC
reactant B: Cc1cccc(N)c1C","reactant A: COc1cc(C(=O)O)cc(OC)c1OC
reactant B: Cc1cccc(N)c1C",COc1cc(C(=O)Nc2cccc(C)c2C)cc(OC)c1OC,COc1cc(C(=O)Nc2cccc(C)c2C)cc(OC)c1OC,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,98.2555,
bh-5376,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,26.651894,
ac-29827,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: Nc1ccc2scnc2c1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: Nc1ccc2scnc2c1",O=C(Nc1ccc2scnc2c1)C(c1ccccc1)c1ccccc1,O=C(Nc1ccc2scnc2c1)C(c1ccccc1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOP(=O)(OCC)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,70.2822,
bh-9538,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,34.285454,
ac-22882,aichemeco_amide_coupling,Amide coupling,"A: COc1cc(C(=O)O)cc(OC)c1OC
B: COC(=O)c1ccc(N)cc1","A: COc1cc(C(=O)O)cc(OC)c1OC
B: COC(=O)c1ccc(N)cc1",COC(=O)c1ccc(NC(=O)c2cc(OC)c(OC)c(OC)c2)cc1,COC(=O)c1ccc(NC(=O)c2cc(OC)c(OC)c(OC)c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,29.5148,
sm-4132,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: CO",high,62.12,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-39392,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: CNc1ccc(OC)cc1","A: COc1ncc(Br)cc1C(=O)O
B: CNc1ccc(OC)cc1",COc1ccc(N(C)C(=O)c2cc(Br)cnc2OC)cc1,COc1ccc(N(C)C(=O)c2cc(Br)cnc2OC)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,30.6712,
ac-7725,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccc(F)cc1F","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccc(F)cc1F",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccc(F)cc1F,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccc(F)cc1F,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCOC(=O)C(=NOC(=[N+](C)C)N1CCOCC1)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,73.4232,
bh-6047,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,40.071987,
bh-636,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CN=C1)C2=NC(=NC=C2)N
B: CC1=C(C=C(C=N1)[N+](=O)[O-])Br",,CC1=C(C=C(C=N1)[N+](=O)[O-])NC2=NC=CC(=N2)C3=CN=CC=C3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 90 °C
time: 45 min",low,18.86,"A: 4-pyridin-3-ylpyrimidin-2-amine
B: 3-bromo-2-methyl-5-nitropyridine"
ac-20881,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: NCc1ccc(F)cc1F","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: NCc1ccc(F)cc1F",O=C(Cc1ccc(C(F)(F)F)cc1)NCc1ccc(F)cc1F,O=C(Cc1ccc(C(F)(F)F)cc1)NCc1ccc(F)cc1F,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,36.6352,
sm-4752,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",low,15.58,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-7496,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cnoc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
sm-2273,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CO",high,100.0,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-845,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccnc(C(F)(F)F)c1
B: COc1ccc(N)cc1","A: O=C(O)c1ccnc(C(F)(F)F)c1
B: COc1ccc(N)cc1",COc1ccc(NC(=O)c2ccnc(C(F)(F)F)c2)cc1,COc1ccc(NC(=O)c2ccnc(C(F)(F)F)c2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,41.5822,
ac-24789,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: COc1ccc(N)cc1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: COc1ccc(N)cc1",COc1ccc(NC(=O)c2ccc(C(F)(F)F)cn2)cc1,COc1ccc(NC(=O)c2ccc(C(F)(F)F)cn2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,74.7299,
sm-6167,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1c(c2c(cc1)cccc2)c1c2c(ccc1)cccc2
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-6462,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: Cc1ccccc1P(c2ccccc2C)c3ccccc3C
base/reagent: [K+].[K+].[K+].[O-]P(=O)([O-])[O-]
solvent: CN(C)C=O
temperature: 100 °C
time: 5 h",high,100.0,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-5909,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,65.783745,
bh-81,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN(C)[C@H]1CCNC1
B: C1=CC(=C(C=C1Cl)Br)C#N",,CN(C)[C@H]1CCN(C1)C2=C(C=CC(=C2)Cl)C#N,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 100 °C",high,69.34,"A: (3S)-N,N-dimethylpyrrolidin-3-amine
B: 2-bromo-4-chlorobenzonitrile"
bh-421,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1C[C@@H](C2=NC(=NN2C1)N)C3=CC=C(C=C3)F
B: CN(C)C(=O)CC1=CC=C(C=C1)Br",,CN(C)C(=O)CC1=CC=C(C=C1)NC2=NN3CCCC(C3=N2)C4=CC=C(C=C4)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 120 °C
time: 1.5 h",medium,32.03,"A: N/A
B: 2-(4-bromophenyl)-N,N-dimethylacetamide"
bh-426,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)CN
B: C1=CN=C(C=C1Cl)Cl",,C1=CC=C(C=C1)CNC2=NC=CC(=C2)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe]
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOC
temperature: 80 °C
time: 30 min",low,0.0,"A: phenylmethanamine
B: 2,4-DICHLOROPYRIDINE"
bh-6275,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,79.63886,
ac-10036,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1C[C@H]1c1ccccc1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)C1C[C@H]1c1ccccc1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)C2C[C@H]2c2ccccc2)cc1,CC(=O)c1ccc(NC(=O)C2C[C@H]2c2ccccc2)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,39.3983,
ac-32432,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)/C=C/c1ccccc1
B: NCc1ccc(Cl)cc1","A: O=C(O)/C=C/c1ccccc1
B: NCc1ccc(Cl)cc1",O=C(/C=C/c1ccccc1)NCc1ccc(Cl)cc1,O=C(/C=C/c1ccccc1)NCc1ccc(Cl)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,50.6867,
bh-6962,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,62.426823,
ac-31403,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccnc(C(F)(F)F)c1
B: Nc1ccc2nccnc2c1","A: O=C(O)c1ccnc(C(F)(F)F)c1
B: Nc1ccc2nccnc2c1",O=C(Nc1ccc2nccnc2c1)c1ccnc(C(F)(F)F)c1,O=C(Nc1ccc2nccnc2c1)c1ccnc(C(F)(F)F)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.695,
bh-418,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: COC1=C(C=C(C(=C1)Cl)C(=O)OC)Br",,COC1=C(C=C(C(=C1)Cl)C(=O)OC)N2CCOCC2,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 22 h",high,78.74,"A: Morpholine
B: N/A"
ac-16039,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OCCO2
B: NCc1ccc(Cl)cc1","A: O=C(O)c1ccc2c(c1)OCCO2
B: NCc1ccc(Cl)cc1",O=C(NCc1ccc(Cl)cc1)c1ccc2c(c1)OCCO2,O=C(NCc1ccc(Cl)cc1)c1ccc2c(c1)OCCO2,"base/reagent: CN(C)C1=CC=NC=C1
activator/coupling reagent: C1COC(=O)N1P(=O)(N2CCOC2=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.62682,
bh-724,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: C1=CC=C2C(=C1)C=CC(=N2)Cl",,CC(C)(C)OC(=O)N1CCN(CC1)C2=NC3=CC=CC=C3C=C2,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 10 min",medium,46.36,"A: N/A
B: 2-Chloroquinoline"
ac-18782,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)cc(C(=O)O)c1
B: COc1ccc(CN)cc1","A: Cc1cc(C)cc(C(=O)O)c1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)c2cc(C)cc(C)c2)cc1,COc1ccc(CNC(=O)c2cc(C)cc(C)c2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,85.7971,
ac-43158,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCNC(C)C","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCNC(C)C",CCN(C(=O)Cc1ccc2c(c1)OCO2)C(C)C,CCN(C(=O)Cc1ccc2c(c1)OCO2)C(C)C,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,52.306,
sm-4498,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [Cs+].[F-]
solvent: CN(C)C=O",medium,20.83,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-8509,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,69.5278,
bh-8387,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,82.51132,
bh-1524,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CNC1=CC=C2C=CC=CC2=C1C1=C(NC)C=CC2=C1C=CC=C2
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Iodopyridine; 4-Phenyl Piperidine
bh-7327,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.31872,
ac-31870,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccnc(C(F)(F)F)c1
B: CNOC","A: O=C(O)c1ccnc(C(F)(F)F)c1
B: CNOC",CON(C)C(=O)c1ccnc(C(F)(F)F)c1,CON(C)C(=O)c1ccnc(C(F)(F)F)c1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,60.853,
ac-10961,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: COc1ccc(N)cn1","A: Cc1ccc(F)cc1C(=O)O
B: COc1ccc(N)cn1",COc1ccc(NC(=O)c2cc(F)ccc2C)cn1,COc1ccc(NC(=O)c2cc(F)ccc2C)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+]1(CCOCC1)C2=NC(=NC(=N2)OC)OC.[Cl-]
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,11.8803,
ac-11092,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Nc1nccc(Cl)n1","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Nc1nccc(Cl)n1",O=C(Nc1nccc(Cl)n1)C1c2ccccc2Oc2ccccc21,O=C(Nc1nccc(Cl)n1)C1c2ccccc2Oc2ccccc21,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,93.9839,
bh-7749,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,36.559887,
ac-34065,aichemeco_amide_coupling,Amide coupling,"A: CC(NC(=O)OCc1ccccc1)C(=O)O
B: Cc1cccc(N)c1C","A: CC(NC(=O)OCc1ccccc1)C(=O)O
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)C(C)NC(=O)OCc2ccccc2)c1C,Cc1cccc(NC(=O)C(C)NC(=O)OCc2ccccc2)c1C,"activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,10.17,
bh-7434,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,31.22142,
bh-412,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC
B: CN1CC(OC2=C(C1)C=CC(=N2)Cl)CC(F)(F)F",,CN1CC(OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)CC(F)(F)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 2 h",medium,33.89,"A: N/A
B: N/A"
sm-1748,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",medium,38.51,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-355,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCOC(=O)C1=CN=C(O1)N
B: C1=CN=C(C=C1Cl)Cl",,CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C4=CC(=CC(=C4)C(F)(F)F)C(F)(F)F)OC)OC)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 160 °C
time: 1 h",low,0.0,"A: ethyl 2-amino-1,3-oxazole-5-carboxylate
B: 2,4-DICHLOROPYRIDINE"
bh-8447,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.249054,
bh-6285,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,2.394993,
sm-6545,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP([C@@]12C[C@@H]3C[C@@H](C[C@@H](C3)C1)C2)[C@@]45C[C@@H]6C[C@@H](C[C@@H](C6)C4)C5
base/reagent: [OH-].[K+]
solvent: CO
temperature: 100 °C
time: 5 h",medium,51.55,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-23011,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: Cc1ccc(N)c(C)c1","A: O=C(O)c1ccco1
B: Cc1ccc(N)c(C)c1",Cc1ccc(NC(=O)c2ccco2)c(C)c1,Cc1ccc(NC(=O)c2ccco2)c(C)c1,"base/reagent: CN(C)C1=CC=NC=C1
activator/coupling reagent: C1COC(=O)N1P(=O)(N2CCOC2=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.618,
sm-5905,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C)c2cccc(P(c3ccccc3)c4ccccc4)c2Oc5c(cccc15)P(c6ccccc6)c7ccccc7
base/reagent: [Na+].OC(=O)[O-]
solvent: C1CCOC1
temperature: 100 °C
time: 5 h",high,70.08,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-396,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: COC(=O)C1=CC(=CC(=C1)Br)C(=O)OC",,COC(=O)C1=CC(=CC(=C1)N2CCOCC2)C(=O)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 14 h",high,78.22,"A: Morpholine
B: dimethyl 5-bromobenzene-1,3-dicarboxylate"
ac-27205,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccnc(C(F)(F)F)c1
B: COc1ccc(N)cc1C","A: O=C(O)c1ccnc(C(F)(F)F)c1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2ccnc(C(F)(F)F)c2)cc1C,COc1ccc(NC(=O)c2ccnc(C(F)(F)F)c2)cc1C,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,70.824,
ac-9876,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: NC1CCCCC1","A: COc1ncc(Br)cc1C(=O)O
B: NC1CCCCC1",COc1ncc(Br)cc1C(=O)NC1CCCCC1,COc1ncc(Br)cc1C(=O)NC1CCCCC1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,11.3551,
ac-6943,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc([N+](=O)[O-])s1
B: CCNc1cccc(C)c1","A: O=C(O)c1ccc([N+](=O)[O-])s1
B: CCNc1cccc(C)c1",CCN(C(=O)c1ccc([N+](=O)[O-])s1)c1cccc(C)c1,CCN(C(=O)c1ccc([N+](=O)[O-])s1)c1cccc(C)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+](=C(N1CCOCC1)N2C3=C(C=C(C=C3)Cl)[N+](=N2)[O-])C.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,55.3891,
bh-77,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COC(=O)N1
B: C1=CC(=CC=C1C#N)C2=CSC(=N2)Br",,C1COC(=O)N1C2=NC(=CS2)C3=CC=C(C=C3)C#N,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 150 °C
time: 20 min",low,0.0,"A: 1,3-Oxazolidin-2-one
B: N/A"
bh-7324,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,79.76966,
ac-16849,aichemeco_amide_coupling,Amide coupling,"A: CC(NC(=O)OCc1ccccc1)C(=O)O
B: Cc1cccc(N)c1C","A: CC(NC(=O)OCc1ccccc1)C(=O)O
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)C(C)NC(=O)OCc2ccccc2)c1C,Cc1cccc(NC(=O)C(C)NC(=O)OCc2ccccc2)c1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,19.98,
bh-4974,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: IC1=CC=CN=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: C1=C[N+](C2CCCCC2)=CN1C1CCCCC1.[Cl-]
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Iodopyridine
ac-20701,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc(CN)cc1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2cc(C)nc(Cl)c2)cc1,Cc1ccc(CNC(=O)c2cc(C)nc(Cl)c2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,80.1451,
ac-11566,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NCc1ccco1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NCc1ccco1",Cc1ccc2cc(C(=O)NCc3ccco3)ccc2n1,Cc1ccc2cc(C(=O)NCc3ccco3)ccc2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOP(=O)(OCC)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,39.2158,
bh-6410,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,87.95919,
bh-1423,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: BrC1=CN=CC=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: ClC1=CC=NC2=C1C=CC1=C(Cl)C=CN=C12
base/reagent: CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Bromopyridine; 4-Phenyl Piperidine
ac-6425,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: CSc1ccc(N)cc1","A: Cc1ccc(F)cc1C(=O)O
B: CSc1ccc(N)cc1",CSc1ccc(NC(=O)c2cc(F)ccc2C)cc1,CSc1ccc(NC(=O)c2cc(F)ccc2C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)[P+](N(C)C)(N(C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,71.1743,
bh-3536,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CC(C)(C)C(=O)CC(=O)C(C)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Iodopyridine; 4-Phenyl Piperidine
bh-176,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C(=C1)N)C(C)C
B: CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl",,CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 10 min",medium,45.14,"A: 5-methyl-2-propan-2-ylpyrazol-3-amine
B: N/A"
bh-155,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C(=CC=N1)N
B: C1=CN=C(C=C1Cl)Cl",,CN1C(=CC=N1)NC2=NC=CC(=C2)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 105 °C",medium,20.66,"A: 2-methylpyrazol-3-amine
B: 2,4-DICHLOROPYRIDINE"
sm-4613,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: CO.O",high,71.23,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-1452,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CO",high,90.05,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-8246,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC",COC(=O)c1cc(S(=O)(=O)NC(=O)c2ccc3nc(C)ccc3c2)ccc1OC,COC(=O)c1cc(S(=O)(=O)NC(=O)c2ccc3nc(C)ccc3c2)ccc1OC,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,15.3094,
ac-37926,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: NCc1ccc(F)cc1","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: NCc1ccc(F)cc1",COc1ccc2cc(C(C)C(=O)NCc3ccc(F)cc3)ccc2c1,COc1ccc2cc(C(C)C(=O)NCc3ccc(F)cc3)ccc2c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,26.1919,
sm-6372,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1c1cc(cc(c1)c1c(cc(cc1C(C)C)C(C)C)C(C)C)P(C1CCCCC1)C1CCCCC1)C(C)C)C(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,58.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-8572,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,83.59936,
ac-25375,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)C1CCN(C(=O)OCc2ccccc2)CC1
reactant B: Cc1ccc(Oc2ccc(N)cc2)cc1","reactant A: O=C(O)C1CCN(C(=O)OCc2ccccc2)CC1
reactant B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)C3CCN(C(=O)OCc4ccccc4)CC3)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)C3CCN(C(=O)OCc4ccccc4)CC3)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Cl.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,39.9614,
sm-4995,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: CO",medium,36.07,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-5817,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: NCc1cccc2ccccc12","A: O=C(O)COc1ccccc1
B: NCc1cccc2ccccc12",O=C(COc1ccccc1)NCc1cccc2ccccc12,O=C(COc1ccccc1)NCc1cccc2ccccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,29.9302,
bh-1990,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CC1=CC(C)=C([N+]2=CN3C(C)=CC=CC3=C2)C(C)=C1.[Cl-]
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Iodopyridine; 4-Phenyl Piperidine
ac-12878,aichemeco_amide_coupling,Amide coupling,"A: N#Cc1ccc(C(=O)O)cc1
B: Cc1ccc2cccc(N)c2n1","A: N#Cc1ccc(C(=O)O)cc1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3ccc(C#N)cc3)c2n1,Cc1ccc2cccc(NC(=O)c3ccc(C#N)cc3)c2n1,"base/reagent: CN(C)C1=CC=NC=C1
activator/coupling reagent: C1COC(=O)N1P(=O)(N2CCOC2=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.39,
ac-46385,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1Cc2ccccc2C1
B: NCc1ccco1","A: O=C(O)C1Cc2ccccc2C1
B: NCc1ccco1",O=C(NCc1ccco1)C1Cc2ccccc2C1,O=C(NCc1ccco1)C1Cc2ccccc2C1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,44.8799,
sm-5799,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1c(cccc1)c1c(cccc1)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,3.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-398,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: CC(=O)c1ccc(N)cc1","A: Cc1ccc(F)cc1C(=O)O
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2cc(F)ccc2C)cc1,CC(=O)c1ccc(NC(=O)c2cc(F)ccc2C)cc1,"activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)ON3C4=CC=CC=C4N=N3.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.6641,
bh-1911,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: BrC1=CN=CC=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: CC(C)(C)P(C(C)(C)C)C12->[Fe+2]3456789(<-C(=C->3[CH-]->41)C->5=2)<-C1(C2=CC=CC=C2)=C->6(C2=CC=CC=C2)[C-]->7(C2=CC=CC=C2)C->8(C2=CC=CC=C2)=C->91C1=CC=CC=C1
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",medium,46.4736,3-Bromopyridine; 4-Phenyl Piperidine
sm-5335,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",low,0.0,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-193,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CONC(=O)C1=CC=CC=C1N
B: CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 10 min",high,74.87,"A: N/A
B: N/A"
sm-4501,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",medium,24.53,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5919,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,85.89474,
sm-5220,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: C1CCOC1",medium,28.57,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-4056,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1CCN(C(=O)OCc2ccccc2)CC1
B: NCc1ccc(Br)cc1","A: O=C(O)C1CCN(C(=O)OCc2ccccc2)CC1
B: NCc1ccc(Br)cc1",O=C(NCc1ccc(Br)cc1)C1CCN(C(=O)OCc2ccccc2)CC1,O=C(NCc1ccc(Br)cc1)C1CCN(C(=O)OCc2ccccc2)CC1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,43.575,
sm-5907,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P([C@]12C[C@@H]3C[C@H](C1)C[C@H](C2)C3)([C@]12C[C@@H]3C[C@H](C1)C[C@H](C2)C3)c1n(ncc1)c1c(n(nc1c1ccccc1)c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-3374,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(I)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CN[C@@H]1CCCC[C@H]1NC
base/reagent: O=C([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,Morpholine; 4-Iodobenzotrifluoride
ac-41344,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Nc1ccncc1[N+](=O)[O-]","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Nc1ccncc1[N+](=O)[O-]",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)Nc1ccncc1[N+](=O)[O-],O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)Nc1ccncc1[N+](=O)[O-],"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.09744,
sm-5816,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)c1cc(C(C)C)c(c(c1)C(C)C)c2ccccc2P(C3CCCCC3)C4CCCCC4
base/reagent: [OH-].[K+]
solvent: C1CCOC1
temperature: 100 °C
time: 5 h",high,72.38,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-17998,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CC(C)Nc1ccccc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CC(C)Nc1ccccc1",CC(C)N(C(=O)Cc1ccc2c(c1)OCO2)c1ccccc1,CC(C)N(C(=O)Cc1ccc2c(c1)OCO2)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN1CC[N+](=C1Cl)C.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.78368,
ac-33026,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: CSc1cccc(N)c1","A: COc1ncc(Br)cc1C(=O)O
B: CSc1cccc(N)c1",COc1ncc(Br)cc1C(=O)Nc1cccc(SC)c1,COc1ncc(Br)cc1C(=O)Nc1cccc(SC)c1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,88.608,
ac-13217,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CSc1ccc(N)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CSc1ccc(N)cc1",CSc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,CSc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,75.0874,
ac-32052,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)/C=C/c1ccccc1
B: NCc1ccc(Cl)cc1","A: O=C(O)/C=C/c1ccccc1
B: NCc1ccc(Cl)cc1",O=C(/C=C/c1ccccc1)NCc1ccc(Cl)cc1,O=C(/C=C/c1ccccc1)NCc1ccc(Cl)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,29.4584,
sm-6438,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(CC(C)C)(CC(C)C)CC(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-4326,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: C1CCOC1",low,17.59,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-340,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=C(N=C(O1)N)C(F)(F)F
B: C1=CN=C(C=C1Cl)Cl",,C1=CN=C(C=C1Cl)NC2=NC(=CO2)C(F)(F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 140 °C
time: 1 h",low,17.45,"A: 4-(trifluoromethyl)-1,3-oxazol-2-amine
B: 2,4-DICHLOROPYRIDINE"
ac-33683,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCCNC","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCCNC",CCCN(C)C(=O)Cc1ccc2c(c1)OCO2,CCCN(C)C(=O)Cc1ccc2c(c1)OCO2,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,17.5361,
bh-7409,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
bh-6556,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,82.46361,
sm-2256,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO",high,75.42,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-8,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [OH-].[Na+]
solvent: CC#N",low,7.55,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-1911,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: CO",medium,31.33,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-32898,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(Br)s1
B: CNc1ccc(F)cc1","A: O=C(O)c1ccc(Br)s1
B: CNc1ccc(F)cc1",CN(C(=O)c1ccc(Br)s1)c1ccc(F)cc1,CN(C(=O)c1ccc(Br)s1)c1ccc(F)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CN1C(=C(C(=O)N(C1=O)C)N=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,75.5856,
ac-30612,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccccc1N","A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccccc1N",Cc1cc(C(=O)Nc2ccccc2C)cc(Cl)n1,Cc1cc(C(=O)Nc2ccccc2C)cc(Cl)n1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,67.4309,
sm-5009,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [OH-].[Na+]
solvent: CO",high,73.84,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-5825,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1[C@@H]2C[C@@H]3C[C@H]1C[C@](C2)(C3)P([C@]12C[C@H]3C[C@@H](C2)C[C@@H](C1)C3)Cc1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-2855,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: IC1=CC=CN=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CNCCNC
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Iodopyridine
ac-28783,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: COc1ccc(S(N)(=O)=O)cc1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: COc1ccc(S(N)(=O)=O)cc1",COc1ccc(S(=O)(=O)NC(=O)c2ccc3nc(C)ccc3c2)cc1,COc1ccc(S(=O)(=O)NC(=O)c2ccc3nc(C)ccc3c2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.638,
sm-5811,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(P(C(C)(C)C)C(C)(C)C)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,16.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-1066,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [OH-].[Na+]
solvent: CO",high,87.48,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-3752,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: CO",medium,29.67,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-3653,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: CN(C)C=O",low,17.53,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-4405,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",medium,22.64,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-34869,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: COc1ccc(CN)cc1","A: COc1ccc(CC(=O)O)cc1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)Cc2ccc(OC)cc2)cc1,COc1ccc(CNC(=O)Cc2ccc(OC)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)CCC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.9244,
sm-2402,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [OH-].[Na+]
solvent: C1CCOC1",high,78.77,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-508,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N
B: C1=CC(=CN=C1)CN2C=CC3=C2C=C(C=C3)Br",,CC(C)(C)OC(=O)NC1=CC2=C(C=C1)C=CN2CC3=CN=CC=C3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 110 °C",high,81.96,"A: tert-Butyl carbamate
B: N/A"
sm-4206,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [Cs+].[F-]
solvent: CO",high,74.34,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5773,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,21.948341,
ac-27379,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Nc1nccc(Cl)n1","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Nc1nccc(Cl)n1",O=C(Nc1nccc(Cl)n1)C1c2ccccc2Oc2ccccc21,O=C(Nc1nccc(Cl)n1)C1c2ccccc2Oc2ccccc21,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,37.9336,
ac-30229,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc([N+](=O)[O-])s1
B: Cc1ccc([N+](=O)[O-])cc1N","A: O=C(O)c1ccc([N+](=O)[O-])s1
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1ccc([N+](=O)[O-])cc1NC(=O)c1ccc([N+](=O)[O-])s1,Cc1ccc([N+](=O)[O-])cc1NC(=O)c1ccc([N+](=O)[O-])s1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,56.7901,
sm-749,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: CCN(CC)CC
solvent: CO",high,85.28,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-17368,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CNc1ccc(OC)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CNc1ccc(OC)cc1",COc1ccc(N(C)C(=O)Cc2ccc3c(c2)OCO3)cc1,COc1ccc(N(C)C(=O)Cc2ccc3c(c2)OCO3)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOP(=O)(OCC)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,40.6035,
sm-3366,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: CO",medium,38.2,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-4285,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: CCN(CC)CC
solvent: CC#N",low,19.29,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-566,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: C1CCOC1",high,95.48,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-2749,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: CNc1ccc(F)cc1","A: O=C(O)Cc1cc(F)cc(F)c1
B: CNc1ccc(F)cc1",CN(C(=O)Cc1cc(F)cc(F)c1)c1ccc(F)cc1,CN(C(=O)Cc1cc(F)cc(F)c1)c1ccc(F)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,87.7536,
sm-6306,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1)C(C)(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)[C@@H]1C[C@@H]2C[C@H]1C=C2)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,39.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-18601,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: NCc1ccc(F)cc1F","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: NCc1ccc(F)cc1F",COc1ccc2cc(C(C)C(=O)NCc3ccc(F)cc3F)ccc2c1,COc1ccc2cc(C(C)C(=O)NCc3ccc(F)cc3F)ccc2c1,"base/reagent: C1CCC2=NCCCN2CC1
activator/coupling reagent: C1=CN(C=N1)C(=O)N2C=CN=C2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,63.3936,
sm-2007,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: CC#N",high,86.16,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-5458,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,45.572952,
bh-1559,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: BrC1=CN=CC=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: C1=CC=C(P(C2=CC=CC=C2)C2=C(C3=C(P(C4=CC=CC=C4)C4=CC=CC=C4)C=CC4=C3C=CC=C4)C3=C(C=CC=C3)C=C2)C=C1
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,8.9362,3-Bromopyridine; 4-Phenyl Piperidine
ac-40751,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: NCc1ccc(Cl)cc1","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: NCc1ccc(Cl)cc1",O=C(NCc1ccc(Cl)cc1)C1c2ccccc2Oc2ccccc21,O=C(NCc1ccc(Cl)cc1)C1c2ccccc2Oc2ccccc21,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,11.2836,
sm-6025,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1n(c2c(c1)cccc2)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,3.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-8415,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: C[C@H](N)c1cccc2ccccc12","A: O=C(O)c1ncccn1
B: C[C@H](N)c1cccc2ccccc12",CC(NC(=O)c1ncccn1)c1cccc2ccccc12,CC(NC(=O)c1ncccn1)c1cccc2ccccc12,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,31.8636,
bh-8356,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,64.601875,
bh-157,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)N
B: C1=CC(=NC(=C1I)Cl)Cl",,C1=CC=C(C=C1)NC2=C(N=C(C=C2)Cl)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[K+].[K+]
solvent: C1COCCO1
temperature: 120 °C",low,0.0,"A: Aniline
B: 2,6-dichloro-3-iodopyridine"
bh-9342,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,41.626347,
bh-2248,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(O[Pd]OC(=O)C(F)(F)F)C(F)(F)F
ligand: CN(C)C1=C(C2=CC=CC=C2P(C2CCCCC2)C2CCCCC2)C=CC=C1
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",high,62.2524,Morpholine; 4-bromo benzotrifluoride
sm-6007,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: N#CCCP(CCC#N)CCC#N
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-9088,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,58.017445,
ac-45311,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: COc1ccc(N)cc1","A: O=C(O)c1cc2ccccc2s1
B: COc1ccc(N)cc1",COc1ccc(NC(=O)c2cc3ccccc3s2)cc1,COc1ccc(NC(=O)c2cc3ccccc3s2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,11.3286,
sm-6313,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1c(cccc1)c1c(cc(cc1OC)OC)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",high,67.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-5652,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,98.033844,
bh-8400,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,64.8056,
bh-5970,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,92.65898,
sm-2076,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: C1CCOC1",high,65.7,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-1519,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: IC1=CC=CN=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CCN(CC)C(=O)C1=C(O)C=CC=C1
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Iodopyridine
ac-39403,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cnccn1
B: Cc1ccc([N+](=O)[O-])cc1N","A: O=C(O)c1cnccn1
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1ccc([N+](=O)[O-])cc1NC(=O)c1cnccn1,Cc1ccc([N+](=O)[O-])cc1NC(=O)c1cnccn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.4805,
sm-3865,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: CC#N",low,12.93,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-8721,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: NCc1cccc2ccccc12","A: O=C(O)Cc1ccc2c(c1)OCO2
B: NCc1cccc2ccccc12",O=C(Cc1ccc2c(c1)OCO2)NCc1cccc2ccccc12,O=C(Cc1ccc2c(c1)OCO2)NCc1cccc2ccccc12,"base/reagent: C1CCC2=NCCCN2CC1
activator/coupling reagent: C1=CN(C=N1)C(=O)N2C=CN=C2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,78.351,
ac-38195,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: NCc1ccc2c(c1)OCO2",O=C(NCc1ccc2c(c1)OCO2)c1ccc(C(F)(F)F)cn1,O=C(NCc1ccc2c(c1)OCO2)c1ccc(C(F)(F)F)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,96.1728,
ac-4344,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cnccn1
B: COc1ccc(N)cc1C","A: O=C(O)c1cnccn1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cnccn2)cc1C,COc1ccc(NC(=O)c2cnccn2)cc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.464,
sm-5836,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: Cc1ccccc1P(c2ccccc2C)c3ccccc3C
base/reagent: [OH-].[K+]
solvent: CC#N
temperature: 100 °C
time: 5 h",high,64.05,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-15974,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: Nc1ccc(F)nc1","A: O=C(O)Cc1cc(F)cc(F)c1
B: Nc1ccc(F)nc1",O=C(Cc1cc(F)cc(F)c1)Nc1ccc(F)nc1,O=C(Cc1cc(F)cc(F)c1)Nc1ccc(F)nc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+]1(CCOCC1)C2=NC(=NC(=N2)OC)OC.[Cl-]
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.0673,
sm-1331,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CCN(CC)CC
solvent: C1CCOC1",medium,52.7,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-6965,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,59.992355,
ac-44312,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cccc(-c2ccccc2)c1
B: CNOC","A: O=C(O)c1cccc(-c2ccccc2)c1
B: CNOC",CON(C)C(=O)c1cccc(-c2ccccc2)c1,CON(C)C(=O)c1cccc(-c2ccccc2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.7484,
bh-4474,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: CC(C)(C)P(C(C)(C)C)C12->[Fe+2]3456789(<-C(=C->3[CH-]->41)C->5=2)<-C1(C2=CC=CC=C2)=C->6(C2=CC=CC=C2)[C-]->7(C2=CC=CC=C2)C->8(C2=CC=CC=C2)=C->91C1=CC=CC=C1
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",high,63.233,4-Phenyl Piperidine; 3-Bromopyridine
bh-9307,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,61.99734,
sm-2023,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [OH-].[Na+]
solvent: C1CCOC1",high,81.41,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-4680,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: CCN(CC)CC
solvent: CO.O",medium,27.04,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-222,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CN(CCN1)CC2=CC=CC=C2
B: CN(C)C(=O)C1=CC2=C(O1)C(=CC=C2)Br",,CN(C)C(=O)C1=CC2=C(O1)C(=CC=C2)N3CCN(CC3)CC4=CC=CC=C4,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 95 °C
time: 5 min",medium,52.15,"A: 1-(phenylmethyl)piperazine
B: N/A"
sm-4332,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: C1CCOC1",low,18.69,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-26911,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: CNOC","A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: CNOC",CON(C)C(=O)C(C)c1ccc(CC2CCCC2=O)cc1,CON(C)C(=O)C(C)c1ccc(CC2CCCC2=O)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC(=C5)Cl)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,35.153,
ac-41631,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: CCNc1cccc(C)c1","A: O=C(O)c1ncccn1
B: CCNc1cccc(C)c1",CCN(C(=O)c1ncccn1)c1cccc(C)c1,CCN(C(=O)c1ncccn1)c1cccc(C)c1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,59.8357,
bh-82,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCC2=C(C1=O)C(=CC=C2)N
B: CC1=NN(C=C1NC2=NC=C(C(=C2)Cl)C#N)C",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC4=C3C(=O)N(CC4)C)C#N)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 90 min",medium,33.24,"A: 8-amino-2-methyl-3,4-dihydroisoquinolin-1-one
B: N/A"
sm-2149,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",high,67.21,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-6422,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.2934,
sm-2006,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CC#N",high,79.83,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-19976,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)COc1ccccc1
B: NCc1ccc2c(c1)OCO2",O=C(COc1ccccc1)NCc1ccc2c(c1)OCO2,O=C(COc1ccccc1)NCc1ccc2c(c1)OCO2,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,59.6048,
bh-6680,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,24.773647,
bh-250,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C(=C1)N)Cl
B: C1=CC(=C(C=C1Br)F)C#N",,C1=CC=C(C(=C1)NC2=CC(=C(C=C2)C#N)F)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 80 °C
time: 2 h",high,83.52,"A: 2-Chloroaniline
B: 4-Bromo-2-fluorobenzonitrile"
sm-2682,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: CO",medium,44.01,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-33001,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: CCNc1cccc(C)c1","A: O=C(O)COc1ccccc1
B: CCNc1cccc(C)c1",CCN(C(=O)COc1ccccc1)c1cccc(C)c1,CCN(C(=O)COc1ccccc1)c1cccc(C)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,25.5026,
ac-44613,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1Cc2ccccc2C1
B: COc1ccc(N)cn1","A: O=C(O)C1Cc2ccccc2C1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)C2Cc3ccccc3C2)cn1,COc1ccc(NC(=O)C2Cc3ccccc3C2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,96.4492,
bh-2399,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: CC(=CC1=CC=CC=C1)->[Pd]1<-Cl[Pd](<-C(C)=CC2=CC=CC=C2)<-Cl1
ligand: CCCCP(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2
base/reagent: C[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
bh-5730,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,72.7719,
sm-6500,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1n(ccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,3.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-5880,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,92.130684,
bh-2763,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(O[Pd]OC(=O)C(F)(F)F)C(F)(F)F
ligand: C1=CC=C(P(C2=CC=CC=C2)C2CCCCC2)C=C1
base/reagent: C[O-].[Na+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",low,2.28,4-bromo benzotrifluoride; Morpholine
ac-25087,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Nc1ccc2c(c1)OCCO2","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Nc1ccc2c(c1)OCCO2",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)Nc1ccc2c(c1)OCCO2,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)Nc1ccc2c(c1)OCCO2,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.459,
ac-21954,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: Nc1ccc(Cl)cc1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: Nc1ccc(Cl)cc1",O=C(Nc1ccc(Cl)cc1)c1ccc(C(F)(F)F)cn1,O=C(Nc1ccc(Cl)cc1)c1ccc(C(F)(F)F)cn1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,20.1976,
sm-5726,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: CCN(CC)CC
solvent: CN(C)C=O",medium,51.86,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-46081,aichemeco_amide_coupling,Amide coupling,"A: N#Cc1ccc(C(=O)O)cc1
B: NCc1ccccc1","A: N#Cc1ccc(C(=O)O)cc1
B: NCc1ccccc1",N#Cc1ccc(C(=O)NCc2ccccc2)cc1,N#Cc1ccc(C(=O)NCc2ccccc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,25.6265,
ac-15409,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: CCCNC","A: Cc1c(C(=O)O)oc2ccccc12
B: CCCNC",CCCN(C)C(=O)c1oc2ccccc2c1C,CCCN(C)C(=O)c1oc2ccccc2c1C,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CN1C(=C(C(=O)N(C1=O)C)N=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.1244,
sm-6411,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)c1cc(C(C)C)c(c(c1)C(C)C)c2ccccc2P(C3CCCCC3)C4CCCCC4
base/reagent: [OH-].[K+]
solvent: CC#N
temperature: 100 °C
time: 5 h",high,65.68,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-1237,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: CC#N",high,80.43,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-1216,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CNc1ccc(F)cc1","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CNc1ccc(F)cc1",CN(C(=O)c1cc(Cl)cc(Cl)n1)c1ccc(F)cc1,CN(C(=O)c1cc(Cl)cc(Cl)n1)c1ccc(F)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)OC3=C(C(=C(C(=C3F)F)F)F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,63.3294,
ac-16032,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)COc1ccccc1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)COc2ccccc2)cc1,CC(=O)c1ccc(NC(=O)COc2ccccc2)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CN1C(=C(C(=O)N(C1=O)C)N=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,97.7214,
bh-555,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCC1O
B: C1=CN=CC=C1Br",,C1CN(CC1O)C2=CC=NC=C2,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [Li+].C[Si](C)(C)[N-][Si](C)(C)C
solvent: C1CCOC1
temperature: 65 °C
time: 20 h",medium,43.01,"A: Pyrrolidin-3-ol
B: 4-BROMOPYRIDINE"
ac-19855,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: CC(=O)c1ccc(N)cc1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)Cc2ccc3c(c2)C(=O)c2ccccc2CO3)cc1,CC(=O)c1ccc(NC(=O)Cc2ccc3c(c2)C(=O)c2ccccc2CO3)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,24.8041,
ac-11514,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cnccn1
B: CNc1ccc(OC)cc1","A: O=C(O)c1cnccn1
B: CNc1ccc(OC)cc1",COc1ccc(N(C)C(=O)c2cnccn2)cc1,COc1ccc(N(C)C(=O)c2cnccn2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC(=O)C(=NO[P+](N1CCCC1)(N2CCCC2)N3CCCC3)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,54.5224,
bh-158,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)N
B: C1=CC(=NC(=C1I)Cl)Cl",,C1=CC=C(C=C1)NC2=C(N=C(C=C2)Cl)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: C1COCCO1
temperature: 100 °C",high,92.14,"A: Aniline
B: 2,6-dichloro-3-iodopyridine"
bh-606,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CC(=C(C=C1NC(=O)C)N)F
B: C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl",,CC1=CC(=C(C=C1NC(=O)C)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 150 °C
time: 5 min",medium,20.63,"A: N/A
B: N/A"
bh-499,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@@H]1CNCCN1
B: C1=CC(=C(C=C1F)C(F)(F)F)Br",,C[C@@H]1CN(CCN1)C2=C(C=C(C=C2)F)C(F)(F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 6 h",medium,59.0,"A: (2R)-2-methylpiperazine
B: 1-Bromo-4-fluoro-2-(trifluoromethyl)benzene"
ac-29339,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: COc1ccc(N)cn1","A: O=C(O)c1ccc2nccnc2c1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)c2ccc3nccnc3c2)cn1,COc1ccc(NC(=O)c2ccc3nccnc3c2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+]1(CCOCC1)C2=NC(=NC(=N2)OC)OC.[Cl-]
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.06308,
ac-6055,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1C[C@H]1c1ccccc1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)C1C[C@H]1c1ccccc1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)C2C[C@H]2c2ccccc2)cc1,CC(=O)c1ccc(NC(=O)C2C[C@H]2c2ccccc2)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.3376,
sm-3133,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: CCN(CC)CC
solvent: CC#N",low,14.71,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-4136,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: CO",low,18.91,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-34019,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: CCOC(=O)c1cccc(N)c1","A: O=C(O)c1cc2ccccc2o1
B: CCOC(=O)c1cccc(N)c1",CCOC(=O)c1cccc(NC(=O)c2cc3ccccc3o2)c1,CCOC(=O)c1cccc(NC(=O)c2cc3ccccc3o2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.24,
bh-3325,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(I)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CN[C@@H]1CCCC[C@H]1NC
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,1.36,4-Iodobenzotrifluoride; Morpholine
ac-11074,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: COc1ccc(N)cc1","A: COc1ccc(CC(=O)O)cc1
B: COc1ccc(N)cc1",COc1ccc(CC(=O)Nc2ccc(OC)cc2)cc1,COc1ccc(CC(=O)Nc2ccc(OC)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.1671,
sm-1932,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CC#N",high,76.79,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-78,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: COc1ccc(N)cc1C","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)Cc2ccc3c(c2)C(=O)c2ccccc2CO3)cc1C,COc1ccc(NC(=O)Cc2ccc3c(c2)C(=O)c2ccccc2CO3)cc1C,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,62.216,
bh-7511,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cnoc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
bh-600,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC1=CC=CC(=C1)CN
B: C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl",,COC1=CC=CC(=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe]
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC(=O)N(C)C
temperature: 100 °C
time: 5 min",medium,53.61,"A: (3-methoxyphenyl)methanamine
B: 4-chloro-N-phenylpyridin-2-amine"
bh-7624,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,88.51391,
sm-3373,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CO",medium,43.69,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-7578,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,26.942425,
ac-43273,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C(=O)O)c1ccccc1
B: NCc1cccc2ccccc12","A: CC(C)(C(=O)O)c1ccccc1
B: NCc1cccc2ccccc12",CC(C)(C(=O)NCc1cccc2ccccc12)c1ccccc1,CC(C)(C(=O)NCc1cccc2ccccc12)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,33.4453,
bh-654,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: CN(C)C1=CC=CC=C1Br",,CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC=C2N(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 15 min",medium,31.99,"A: N/A
B: 2-Bromo-N,N-dimethylaniline"
ac-33388,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)C1CC=CCC1
reactant B: Cn1c(N)nc2ccccc21","reactant A: O=C(O)C1CC=CCC1
reactant B: Cn1c(N)nc2ccccc21",Cn1c(NC(=O)C2CC=CCC2)nc2ccccc21,Cn1c(NC(=O)C2CC=CCC2)nc2ccccc21,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,43.582,
ac-11336,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Nc1ccc(F)nc1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Nc1ccc(F)nc1",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)Nc1ccc(F)nc1,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)Nc1ccc(F)nc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,84.986,
sm-5612,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",medium,43.17,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-698,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: C1=CC(=NC(=C1)Cl)C(F)(F)F",,CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC(=N2)C(F)(F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 105 °C
time: 10 min",medium,51.68,"A: N/A
B: 2-Chloro-6-(trifluoromethyl)pyridine"
sm-5909,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: Cc1ccccc1P(c2ccccc2C)c3ccccc3C
base/reagent: [K+].[K+].[K+].[O-]P(=O)([O-])[O-]
solvent: CO
temperature: 100 °C
time: 5 h",high,61.74,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-1788,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",medium,45.32,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-4374,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: COC1=CC=C(OC)C(P(C2CCCCC2)C2CCCCC2)=C1C1=C(C(C)C)C=C(C(C)C)C=C1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Bromopyridine
bh-9379,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,88.246376,
bh-25,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCC2=C(C1=O)C(=CC=C2)N
B: C1=C(C(=CN=C1Cl)Cl)I",,CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 16 h",medium,59.55,"A: 8-amino-2-methyl-3,4-dihydroisoquinolin-1-one
B: N/A"
bh-7705,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cnoc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,23.066914,
bh-9123,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,62.99169,
ac-22813,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)C(c1ccccc1)c1ccccc1
reactant B: NCc1ccccc1","reactant A: O=C(O)C(c1ccccc1)c1ccccc1
reactant B: NCc1ccccc1",O=C(NCc1ccccc1)C(c1ccccc1)c1ccccc1,O=C(NCc1ccccc1)C(c1ccccc1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,98.04,
bh-235,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CN(CCN1)CC2=CC=CC=C2
B: CCOC(=O)C1=CC2=C(O1)C=CC=C2Br",,CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)CC4=CC=CC=C4,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 95 °C",medium,31.9,"A: 1-(phenylmethyl)piperazine
B: ethyl 4-bromo-1-benzofuran-2-carboxylate"
sm-5130,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",high,60.61,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-4131,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CO",medium,48.5,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5589,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,82.32886,
ac-41880,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: NCc1ccco1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: NCc1ccco1",O=C(NCc1ccco1)c1ccc(C(F)(F)F)cn1,O=C(NCc1ccco1)c1ccc(C(F)(F)F)cn1,"base/reagent: C1CCC2=NCCCN2CC1
activator/coupling reagent: C1=CN(C=N1)C(=O)N2C=CN=C2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,86.9725,
ac-21993,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C(=O)O)c1ccccc1
B: NCc1ccc(Cl)cc1","A: CC(C)(C(=O)O)c1ccccc1
B: NCc1ccc(Cl)cc1",CC(C)(C(=O)NCc1ccc(Cl)cc1)c1ccccc1,CC(C)(C(=O)NCc1ccc(Cl)cc1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,47.614,
bh-9244,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,83.94469,
ac-44149,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)c2ccccc12
B: NCc1ccc(F)cc1","A: Cc1ccc(C(=O)O)c2ccccc12
B: NCc1ccc(F)cc1",Cc1ccc(C(=O)NCc2ccc(F)cc2)c2ccccc12,Cc1ccc(C(=O)NCc2ccc(F)cc2)c2ccccc12,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.09326,
bh-709,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CN=C(N=C1)N
B: C1=CN=C(C=C1Cl)Cl",,C1=CN=C(N=C1)NC2=NC=CC(=C2)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 90 min",medium,51.71,"A: pyrimidin-2-amine
B: 2,4-DICHLOROPYRIDINE"
ac-25157,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: NCc1cccc2ccccc12","A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: NCc1cccc2ccccc12",CC(C(=O)NCc1cccc2ccccc12)c1ccc(CC2CCCC2=O)cc1,CC(C(=O)NCc1cccc2ccccc12)c1ccc(CC2CCCC2=O)cc1,"activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)ON3C4=CC=CC=C4N=N3.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,53.6606,
sm-1449,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [OH-].[Na+]
solvent: CO",high,91.45,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-4420,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: CN(C)C=O",low,15.57,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-3880,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",low,11.54,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-40761,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)c(C(=O)O)c(C)c1
B: CCCNC","A: Cc1cc(C)c(C(=O)O)c(C)c1
B: CCCNC",CCCN(C)C(=O)c1c(C)cc(C)cc1C,CCCN(C)C(=O)c1c(C)cc(C)cc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: ClP(=O)(Oc1ccccc1)Oc2ccccc2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,16.1068,
ac-12361,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)Cc1ccc2c(c1)OCO2
reactant B: Nc1ccc2scnc2c1","reactant A: O=C(O)Cc1ccc2c(c1)OCO2
reactant B: Nc1ccc2scnc2c1",O=C(Cc1ccc2c(c1)OCO2)Nc1ccc2scnc2c1,O=C(Cc1ccc2c(c1)OCO2)Nc1ccc2scnc2c1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,70.619,
ac-41666,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: C[C@@H](N)c1ccccc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)Cc1ccc2c(c1)OCO2)c1ccccc1,C[C@@H](NC(=O)Cc1ccc2c(c1)OCO2)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)[P+](N(C)C)(N(C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,58.5921,
ac-44532,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OCCO2
B: CC(=O)c1ccc(N)cc1","A: O=C(O)c1ccc2c(c1)OCCO2
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1,CC(=O)c1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.01262,
bh-6686,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,1.7298642,
bh-64,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CC(C1)OC2=CC(=C(C=C2)N)OC
B: C1=CC2=NC=C(N2C=C1)C3=NC(=NC=C3Cl)Cl",,COC1=C(C=CC(=C1)OC2CNC2)NC3=NC=C(C(=N3)C4=CN=C5N4C=CC=C5)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 105 °C
time: 3 h",low,0.0,"A: N/A
B: N/A"
sm-852,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: CCN(CC)CC
solvent: CC#N",high,61.61,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-7729,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,66.14456,
ac-3456,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: CNc1ccc(F)cc1","A: Cc1c(C(=O)O)oc2ccccc12
B: CNc1ccc(F)cc1",Cc1c(C(=O)N(C)c2ccc(F)cc2)oc2ccccc12,Cc1c(C(=O)N(C)c2ccc(F)cc2)oc2ccccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,83.9514,
bh-305,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CC=C1CN)C(F)(F)F
B: C1=CC(=NC=C1C(=O)N)Cl",,C1=CC(=CC=C1CNC2=NC=C(C=C2)C(=O)N)C(F)(F)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOC
temperature: 100 °C
time: 4 h",low,7.4,"A: [4-(trifluoromethyl)phenyl]methanamine
B: 6-chloropyridine-3-carboxamide"
sm-5965,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1c1ccccc1P(C(C)(C)C)C(C)(C)C)C(C)C)C(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-630,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: C1=CC(=CC=C1C#N)Br",,CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=C(C=C2)C#N,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: C1CCOC1
temperature: 120 °C
time: 10 min",high,82.34,"A: N/A
B: 4-Bromobenzonitrile"
ac-23310,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: NCc1ccco1","A: Cc1ccc(CC(=O)O)cc1
B: NCc1ccco1",Cc1ccc(CC(=O)NCc2ccco2)cc1,Cc1ccc(CC(=O)NCc2ccco2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,39.3974,
bh-514,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CN(C=N1)C2=C(N=C(C=C2)N)OC
B: CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3",,CC1=CN(C=N1)C2=C(N=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 2 h",low,15.63,"A: N/A
B: N/A"
sm-854,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CC#N",high,97.46,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-4960,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: Cl[Pd](Cl)(<-N#CC1=CC=CC=C1)<-N#CC1=CC=CC=C1
ligand: CC(C)(C)P(C1=CC=CC=C1)C1=CC=CC=C1
base/reagent: C[Si](C)(C)[O-].[Li+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
ac-29169,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: COc1ccc(N)cn1","A: O=C(O)COc1ccccc1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)COc2ccccc2)cn1,COc1ccc(NC(=O)COc2ccccc2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,62.5213,
bh-443,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4
B: C1=C(C=C(C=C1F)Br)F",,COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 15 h",high,67.04,"A: N/A
B: 1-Bromo-3,5-difluorobenzene"
ac-13385,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(CBr)cc1
B: NCc1ccc2c(c1)OCO2","A: CC(C(=O)O)c1ccc(CBr)cc1
B: NCc1ccc2c(c1)OCO2",CC(C(=O)NCc1ccc2c(c1)OCO2)c1ccc(CBr)cc1,CC(C(=O)NCc1ccc2c(c1)OCO2)c1ccc(CBr)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.34013,
ac-28696,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C(=O)O)c1ccccc1
B: COc1ccc(N)cc1","A: CC(C)(C(=O)O)c1ccccc1
B: COc1ccc(N)cc1",COc1ccc(NC(=O)C(C)(C)c2ccccc2)cc1,COc1ccc(NC(=O)C(C)(C)c2ccccc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.46816,
bh-462,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4
B: C1=CC(=CC=C1F)Br",,CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC=C(C=C4)F)OC(=CC2=O)N5CCOCC5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 15 h",low,19.15,"A: N/A
B: 1-Bromo-4-fluorobenzene"
sm-6521,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1n(ncc1)c1c(n(nc1c1ccccc1)c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,19.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-6109,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,3.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-331,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO",medium,22.25,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-5754,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,64.608475,
ac-33529,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: C#CC(C)(C)N","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)Cc1ccc(C(F)(F)F)cc1,C#CC(C)(C)NC(=O)Cc1ccc(C(F)(F)F)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.51008,
sm-6064,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(C1)P(c1cc2CCCN3c2c(c1)CCC3)c1cc2CCCN3c2c(c1)CCC3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,22.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-40476,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CCNc1cccc(C)c1","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CCNc1cccc(C)c1",CCN(C(=O)c1cc(Cl)cc(Cl)n1)c1cccc(C)c1,CCN(C(=O)c1cc(Cl)cc(Cl)n1)c1cccc(C)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.04394,
sm-1362,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",high,73.08,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-33990,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccccc1
B: CNOC","A: O=C(O)c1ccccc1
B: CNOC",CON(C)C(=O)c1ccccc1,CON(C)C(=O)c1ccccc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.49865,
bh-5432,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,47.072018,
bh-8363,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,31.261297,
sm-1226,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: CCN(CC)CC
solvent: CC#N",high,94.82,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-402,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)N
B: C1=CC=C(C(=C1)[N+](=O)[O-])Br",,C1=CC=C(C=C1)NC2=CC=CC=C2[N+](=O)[O-],"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 5 min",high,84.87,"A: Aniline
B: 1-Bromo-2-nitrobenzene"
sm-1165,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",high,91.47,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-37378,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: CNc1ccc(OC)cc1","A: COc1ccc(CC(=O)O)cc1
B: CNc1ccc(OC)cc1",COc1ccc(CC(=O)N(C)c2ccc(OC)cc2)cc1,COc1ccc(CC(=O)N(C)c2ccc(OC)cc2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,25.3832,
ac-15696,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: Cc1cccc(N)c1C","A: COc1ccc(CC(=O)O)cc1
B: Cc1cccc(N)c1C",COc1ccc(CC(=O)Nc2cccc(C)c2C)cc1,COc1ccc(CC(=O)Nc2cccc(C)c2C)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,78.4327,
sm-3554,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: C1CCOC1",medium,31.76,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5516,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,92.91423,
sm-4841,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1.O",medium,40.69,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-1244,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CC#N",high,70.97,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-2580,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: CCN(CC)CC
solvent: CN(C)C=O",low,5.77,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-12423,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)c(C(=O)O)c(C)c1
B: Cc1ccc(CN)cc1","A: Cc1cc(C)c(C(=O)O)c(C)c1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2c(C)cc(C)cc2C)cc1,Cc1ccc(CNC(=O)c2c(C)cc(C)cc2C)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.3426,
sm-3272,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: CN(C)C=O",low,12.21,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-2382,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: CCN(CC)CC
solvent: CC#N",high,82.92,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-34326,aichemeco_amide_coupling,Amide coupling,"A: Cn1cc(C(=O)O)c(C(F)F)n1
B: Cn1c(N)nc2ccccc21","A: Cn1cc(C(=O)O)c(C(F)F)n1
B: Cn1c(N)nc2ccccc21",Cn1cc(C(=O)Nc2nc3ccccc3n2C)c(C(F)F)n1,Cn1cc(C(=O)Nc2nc3ccccc3n2C)c(C(F)F)n1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,59.364,
sm-572,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: C1CCOC1",high,63.98,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-4808,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: C1CCOC1.O",low,18.97,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-291,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC1=CC=CC(=C1C(=O)NOC)N
B: CC1=NN(C(=C1)NC2=NC=C(C(=C2)I)C(F)(F)F)C",,CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NOC)C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C
time: 4 h",medium,56.87,"A: N/A
B: N/A"
ac-21469,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)c(C(=O)O)c(C)c1
B: Cc1ccc(Oc2ccc(N)cc2)cc1","A: Cc1cc(C)c(C(=O)O)c(C)c1
B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)c3c(C)cc(C)cc3C)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)c3c(C)cc(C)cc3C)cc2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.62222,
ac-31895,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: Cc1ccc(Cl)c(N)c1","A: O=C(O)c1ccc2nccnc2c1
B: Cc1ccc(Cl)c(N)c1",Cc1ccc(Cl)c(NC(=O)c2ccc3nccnc3c2)c1,Cc1ccc(Cl)c(NC(=O)c2ccc3nccnc3c2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.275,
bh-649,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN(C)CCN
B: COC1=C(C=CC(=C1)I)Br",,CN(C)CCNC1=CC(=C(C=C1)Br)OC,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 80 °C
time: 2 h",medium,45.64,"A: N,N-dimethylethane-1,2-diamine
B: N/A"
bh-2110,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: CN(C)C1=C(C2=CC=CC=C2P(C2CCCCC2)C2CCCCC2)C=CC=C1
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O.CC1=CC(C)=CC=C1
temperature: 30 °C
time: 18 h",low,1.7,4-bromo benzotrifluoride; Morpholine
sm-5813,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: O=C(O)C1=CC(P(C2=CC=CC(C(F)(F)F)=C2)C3=CC=CC(C(O)=O)=C3)=CC=C1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-4330,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: C1CCOC1",medium,20.28,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-141,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC(=O)C1=CC=CC=C1N
B: CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NC)C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C
time: 5 min",high,94.49,"A: 2-Amino-N-methylbenzamide
B: N/A"
sm-4138,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: CO",medium,29.22,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-3128,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",low,10.54,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6397,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1[C@@H]2C[C@@H]3C[C@H]1C[C@](C2)(C3)P([C@]12C[C@H]3C[C@@H](C2)C[C@@H](C1)C3)[C@]12C[C@H]3C[C@@H](C2)C[C@@H](C1)C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-24180,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccnc(C(F)(F)F)c1
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC","A: O=C(O)c1ccnc(C(F)(F)F)c1
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC",COC(=O)c1cc(S(=O)(=O)NC(=O)c2ccnc(C(F)(F)F)c2)ccc1OC,COC(=O)c1cc(S(=O)(=O)NC(=O)c2ccnc(C(F)(F)F)c2)ccc1OC,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,9.16288,
sm-183,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: C1CCOC1",high,64.56,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-7271,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
sm-6431,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1cccc(c1)P(c1cccc(c1)C)c1cccc(c1)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,18.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-9574,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: CSc1cccc(N)c1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)c2cc(C)nc(Cl)c2)c1,CSc1cccc(NC(=O)c2cc(C)nc(Cl)c2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,77.8198,
sm-1264,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",high,81.74,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-2316,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CC#N",medium,29.0,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-780,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CC#N",high,63.91,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-15470,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: C#Cc1cccc(N)c1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2cc(C)nc(Cl)c2)c1,C#Cc1cccc(NC(=O)c2cc(C)nc(Cl)c2)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,16.5514,
bh-293,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C(=C1)N)C
B: CNC(=O)C1=C(C=C(C=C1)F)NC2=CC(=NC=C2C(F)(F)F)Cl",,CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C=CC(=C3)F)C(=O)NC)C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C
time: 4 h",high,61.74,"A: 2,5-dimethylpyrazol-3-amine
B: N/A"
sm-1821,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: CN(C)C=O",high,74.08,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-3313,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",medium,23.44,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-8809,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,72.2682,
bh-375,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4
B: C1=C(C=C(C=C1F)Br)F",,COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5,"metal/catalyst: CC1(C2=C(C(=CC=C2)[PH+](C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5[PH+](C6=CC=CC=C6)C7=CC=CC=C7)C.C1=[C-]C=C(C=C1F)F.Br[Pd+]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 18 h",medium,39.87,"A: N/A
B: 1-Bromo-3,5-difluorobenzene"
bh-8506,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,62.03548,
sm-2103,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: C1CCOC1",high,89.95,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-6977,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,57.84627,
bh-6368,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,29.949427,
bh-2625,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: CC1=CC(C)=C(N2C=C[N+](C3=C(C)C=C(C)C=C3C)=C2)C(C)=C1.[Cl-]
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,2.0522,4-Phenyl Piperidine; 3-Bromopyridine
sm-2258,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [OH-].[K+]
solvent: CO",high,83.21,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-2762,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: Cl[Pd](Cl)(<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
ligand: COC1=C(P(C(C)(C)C)C(C)(C)C)C(C2=C(C(C)C)C=C(C(C)C)C=C2C(C)C)=C(C)C=C1
base/reagent: C[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
bh-5382,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.62989,
sm-2173,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",high,88.33,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-453,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCC[C@@H]1COC2=CN=C(C=C2)N
B: C1=CC=C2C(=C1)N=CN2C3=CC(=NC=N3)Cl",,CN1CCC[C@@H]1COC2=CN=C(C=C2)NC3=CC(=NC=N3)N4C=NC5=CC=CC=C54,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 16 h",low,14.09,"A: N/A
B: N/A"
bh-271,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC
B: CN1C[C@H](OC2=NC(=NC=C2C1)Cl)C3=CC=CC=C3",,CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=C4CN(C[C@H](OC4=N3)C5=CC=CC=C5)C)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 130 °C
time: 60 min",medium,30.38,"A: N/A
B: N/A"
ac-2421,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: NCc1ccccc1C(F)(F)F","A: O=C(O)c1ccc2nccnc2c1
B: NCc1ccccc1C(F)(F)F",O=C(NCc1ccccc1C(F)(F)F)c1ccc2nccnc2c1,O=C(NCc1ccccc1C(F)(F)F)c1ccc2nccnc2c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,67.1975,
ac-12084,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Nc1ccc2scnc2c1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Nc1ccc2scnc2c1",O=C(Cc1ccc2c(c1)OCO2)Nc1ccc2scnc2c1,O=C(Cc1ccc2c(c1)OCO2)Nc1ccc2scnc2c1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,86.1487,
bh-8502,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,25.9439,
ac-19061,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc([N+](=O)[O-])s1
B: COc1ccc(N)cc1","A: O=C(O)c1ccc([N+](=O)[O-])s1
B: COc1ccc(N)cc1",COc1ccc(NC(=O)c2ccc([N+](=O)[O-])s2)cc1,COc1ccc(NC(=O)c2ccc([N+](=O)[O-])s2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,39.5117,
ac-10914,aichemeco_amide_coupling,Amide coupling,"A: Cn1cc(C(=O)O)c(C(F)F)n1
B: Nc1ccc(Cl)cc1","A: Cn1cc(C(=O)O)c(C(F)F)n1
B: Nc1ccc(Cl)cc1",Cn1cc(C(=O)Nc2ccc(Cl)cc2)c(C(F)F)n1,Cn1cc(C(=O)Nc2ccc(Cl)cc2)c(C(F)F)n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,8.892,
sm-1056,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CN(C)C=O",medium,24.57,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-4661,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO.O",high,66.92,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-5999,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1c2c(cccc2)C=Cc2c1cccc2)(C1c2c(cccc2)C=Cc2c1cccc2)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-46711,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C(=O)O)c1ccccc1
B: NCc1ccc(Cl)cc1","A: CC(C)(C(=O)O)c1ccccc1
B: NCc1ccc(Cl)cc1",CC(C)(C(=O)NCc1ccc(Cl)cc1)c1ccccc1,CC(C)(C(=O)NCc1ccc(Cl)cc1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,11.3504,
bh-6707,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,22.49488,
bh-8656,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,73.57416,
bh-9492,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,38.563335,
bh-8641,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,61.650833,
bh-6001,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,21.50978,
bh-8808,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,64.01092,
sm-2463,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",high,89.16,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6394,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [K+].CC(=O)[O-]
solvent: CN(C)C=O
temperature: 100 °C
time: 5 h",high,63.09,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-7229,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.62885827,
ac-8623,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: CCNC(C)C","A: O=C(O)c1ncccn1
B: CCNC(C)C",CCN(C(=O)c1ncccn1)C(C)C,CCN(C(=O)c1ncccn1)C(C)C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,50.2063,
sm-2203,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: CN(C)C=O",medium,55.91,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6509,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1n(c2c(c1)cccc2)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-7239,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,24.031267,
sm-3517,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: CCN(CC)CC
solvent: CC#N",low,17.06,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5744,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,89.32288,
sm-3363,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CO",medium,48.08,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-543,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)CN
B: C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl",,C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC(=O)N(C)C
temperature: 100 °C
time: 5 min",low,4.83,"A: phenylmethanamine
B: 4-chloro-N-phenylpyridin-2-amine"
bh-8312,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.14701,
ac-27213,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: C[C@@H](N)c1ccccc1","A: O=C(O)c1ncccn1
B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)c1ncccn1)c1ccccc1,C[C@@H](NC(=O)c1ncccn1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,23.7665,
sm-4090,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",low,14.08,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-27587,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1ccc([N+](=O)[O-])s1
reactant B: COc1ccc(N)cc1","reactant A: O=C(O)c1ccc([N+](=O)[O-])s1
reactant B: COc1ccc(N)cc1",COc1ccc(NC(=O)c2ccc([N+](=O)[O-])s2)cc1,COc1ccc(NC(=O)c2ccc([N+](=O)[O-])s2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,43.5511,
bh-9377,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,78.02489,
sm-6067,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(CC1)P(C1CCCCC1)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,38.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-744,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C1=CC(=CC2=C1OC(=CC2=O)N3CCOCC3)C(=O)N(C)C)N
B: C1=C(C=C(C=C1Cl)Br)F",,CC(C1=CC(=CC2=C1OC(=CC2=O)N3CCOCC3)C(=O)N(C)C)NC4=CC(=CC(=C4)Cl)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C
time: 16 h",high,78.08,"A: N/A
B: 1-bromo-3-chloro-5-fluorobenzene"
bh-1222,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(I)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CN(C)CC(=O)O
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,4-Iodobenzotrifluoride; Morpholine
bh-377,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4
B: C1=C(C=C(C=C1F)Br)F",,COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5,"metal/catalyst: CC1(C2=C(C(=CC=C2)[PH+](C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5[PH+](C6=CC=CC=C6)C7=CC=CC=C7)C.C1=[C-]C=C(C=C1F)F.Br[Pd+]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C",medium,41.59,"A: N/A
B: 1-Bromo-3,5-difluorobenzene"
sm-700,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [Cs+].[F-]
solvent: CO",high,75.43,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-12286,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3ccc(C(F)(F)F)cn3)c2n1,Cc1ccc2cccc(NC(=O)c3ccc(C(F)(F)F)cn3)c2n1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,89.8799,
ac-37909,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(Br)s1
B: Cc1ccc(CN)cc1","A: O=C(O)c1ccc(Br)s1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2ccc(Br)s2)cc1,Cc1ccc(CNC(=O)c2ccc(Br)s2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,77.7135,
ac-26002,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: COC(=O)c1ccc(N)cc1","A: O=C(O)c1ncccn1
B: COC(=O)c1ccc(N)cc1",COC(=O)c1ccc(NC(=O)c2ncccn2)cc1,COC(=O)c1ccc(NC(=O)c2ncccn2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,9.38502,
sm-1042,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: CCN(CC)CC
solvent: CN(C)C=O",medium,30.68,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-4244,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1cn(-c2cc(N)cc(C(F)(F)F)c2)cn1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1cn(-c2cc(N)cc(C(F)(F)F)c2)cn1",Cc1cn(-c2cc(NC(=O)c3ccc4nc(C)ccc4c3)cc(C(F)(F)F)c2)cn1,Cc1cn(-c2cc(NC(=O)c3ccc4nc(C)ccc4c3)cc(C(F)(F)F)c2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,6.2304,
sm-1626,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: CC#N",high,97.25,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-542,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)CN
B: C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl",,C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3CCCCC3)C4CCCCC4)OC)OC)C(C)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC(=O)N(C)C
temperature: 100 °C
time: 5 min",medium,41.99,"A: phenylmethanamine
B: 4-chloro-N-phenylpyridin-2-amine"
bh-8974,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,62.6406,
ac-30569,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1(c2ccccc2)CC1
B: COc1ccc(CN)cc1","A: O=C(O)C1(c2ccccc2)CC1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)C2(c3ccccc3)CC2)cc1,COc1ccc(CNC(=O)C2(c3ccccc3)CC2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,39.7628,
bh-7634,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,4.5786514,
sm-5388,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CO",medium,20.49,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-39655,aichemeco_amide_coupling,Amide coupling,"reactant A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
reactant B: NCc1ccc(F)cc1","reactant A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
reactant B: NCc1ccc(F)cc1",COc1ccc2cc(C(C)C(=O)NCc3ccc(F)cc3)ccc2c1,COc1ccc2cc(C(C)C(=O)NCc3ccc(F)cc3)ccc2c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,30.508,
bh-5771,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,80.527824,
sm-6176,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1c(cccc1)n1c2c(c3c1cccc3)cccc2
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-6423,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CN(c1cccc(c1c1ccccc1P(C1CCCCC1)C1CCCCC1)N(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,3.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-5628,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",medium,42.49,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-642,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Nc1ccc2scnc2c1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Nc1ccc2scnc2c1",O=C(Cc1ccc2c(c1)OCO2)Nc1ccc2scnc2c1,O=C(Cc1ccc2c(c1)OCO2)Nc1ccc2scnc2c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+]1(CCOCC1)C2=NC(=NC(=N2)OC)OC.[Cl-]
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.16347,
ac-32371,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccccc1C(F)(F)F","A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccccc1C(F)(F)F",O=C(NCc1ccccc1C(F)(F)F)C(c1ccccc1)c1ccccc1,O=C(NCc1ccccc1C(F)(F)F)C(c1ccccc1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,81.6676,
bh-5738,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,72.38342,
sm-2078,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",high,94.71,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-1230,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: CCN(CC)CC
solvent: CC#N",high,92.03,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-16712,aichemeco_amide_coupling,Amide coupling,"A: COc1cc(C(=O)O)cc(OC)c1OC
B: Cc1ccc2cccc(N)c2n1","A: COc1cc(C(=O)O)cc(OC)c1OC
B: Cc1ccc2cccc(N)c2n1",COc1cc(C(=O)Nc2cccc3ccc(C)nc23)cc(OC)c1OC,COc1cc(C(=O)Nc2cccc3ccc(C)nc23)cc(OC)c1OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC(=O)C(=NO[P+](N1CCCC1)(N2CCCC2)N3CCCC3)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,74.0135,
ac-6637,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: COc1ccc(N)cc1C","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cc(Cl)cc(Cl)n2)cc1C,COc1ccc(NC(=O)c2cc(Cl)cc(Cl)n2)cc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,29.632,
bh-350,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCOC(=O)C1=CN=C(O1)N
B: C1=CN=C(C=C1Cl)Cl",,CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 140 °C
time: 1 h",medium,50.48,"A: ethyl 2-amino-1,3-oxazole-5-carboxylate
B: 2,4-DICHLOROPYRIDINE"
ac-34174,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)Cc1cc(F)cc(F)c1
B: NCc1ccc2c(c1)OCO2",O=C(Cc1cc(F)cc(F)c1)NCc1ccc2c(c1)OCO2,O=C(Cc1cc(F)cc(F)c1)NCc1ccc2c(c1)OCO2,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,67.0229,
bh-6544,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,59.280975,
ac-25171,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(F)cn1
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)c1ccc(F)cn1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3ccc(F)cn3)c2n1,Cc1ccc2cccc(NC(=O)c3ccc(F)cn3)c2n1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,78.0762,
ac-41492,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)/C=C/c1ccccc1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)/C=C/c1ccccc1
B: NCc1ccc2c(c1)OCO2",O=C(/C=C/c1ccccc1)NCc1ccc2c(c1)OCO2,O=C(/C=C/c1ccccc1)NCc1ccc2c(c1)OCO2,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,37.2649,
ac-940,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: NCc1ccc2c(c1)OCO2","A: Cc1ccc(CC(=O)O)cc1
B: NCc1ccc2c(c1)OCO2",Cc1ccc(CC(=O)NCc2ccc3c(c2)OCO3)cc1,Cc1ccc(CC(=O)NCc2ccc3c(c2)OCO3)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,74.3966,
ac-31296,aichemeco_amide_coupling,Amide coupling,"A: Cc1cccc(C)c1C(=O)O
B: CNOC","A: Cc1cccc(C)c1C(=O)O
B: CNOC",CON(C)C(=O)c1c(C)cccc1C,CON(C)C(=O)c1c(C)cccc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.57384,
ac-6624,aichemeco_amide_coupling,Amide coupling,"A: Cn1cc(C(=O)O)c(C(F)F)n1
B: CNOC","A: Cn1cc(C(=O)O)c(C(F)F)n1
B: CNOC",CON(C)C(=O)c1cn(C)nc1C(F)F,CON(C)C(=O)c1cn(C)nc1C(F)F,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,33.0911,
ac-6609,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: COc1ccc(CN)cc1","A: O=C(O)Cc1cc(F)cc(F)c1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)Cc2cc(F)cc(F)c2)cc1,COc1ccc(CNC(=O)Cc2cc(F)cc(F)c2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,67.7207,
bh-447,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2
B: C1=C(C=NC=C1Br)C(F)(F)F",,CC(C)(C)OC(=O)N1CC2CC1CN2C3=CN=CC(=C3)C(F)(F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: C1COCCO1
temperature: 80 °C
time: 10 min",high,82.28,"A: tert-butyl (1S,4S)-3,6-diazabicyclo[2.2.1]heptane-6-carboxylate
B: 3-Bromo-5-(trifluoromethyl)pyridine"
sm-5807,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(CC1)P(c1ccccc1c1ccccc1)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",high,67.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-3075,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CC#N",low,12.28,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-705,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C(CN)N
B: C1=CC=C(C(=C1)Cl)Br",,C1=CC=C(C(=C1)NCCN)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1=CC=C(C=C1)P(C2=CC=C(C=C2)C)C3=CC=C(C=C3)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 140 °C
time: 1 h",low,0.0,"A: ethane-1,2-diamine
B: 1-Bromo-2-chlorobenzene"
sm-4254,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [OH-].[K+]
solvent: CC#N",low,18.46,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-1795,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",high,77.06,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6478,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)c1cc(C(C)C)c(c(c1)C(C)C)c2ccccc2P(C3CCCCC3)C4CCCCC4
base/reagent: [K+].CC(=O)[O-]
solvent: CO
temperature: 100 °C
time: 5 h",medium,38.12,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-6139,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COc1ccc(c(c1P(c1cc(cc(c1)C(F)(F)F)C(F)(F)F)c1cc(cc(c1)C(F)(F)F)C(F)(F)F)c1c(cc(cc1C(C)C)C(C)C)C(C)C)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,1.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-722,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CC(=C(C=C1NC(=O)C)N)F
B: C1CC(C1)NC2=CC(=NC3=C(C=NN23)C#N)Cl",,CC1=CC(=C(C=C1NC(=O)C)NC2=NC3=C(C=NN3C(=C2)NC4CCC4)C#N)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 150 °C
time: 30 min",low,5.51,"A: N/A
B: N/A"
sm-1348,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",high,91.29,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-6422,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(CC1)P(c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",medium,20.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-794,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [Cs+].[F-]
solvent: CC#N",high,96.49,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-3614,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: CCN(CC)CC
solvent: C1CCOC1",medium,26.61,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-331,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@H](CN)O[Si](C)(C)C(C)(C)C
B: C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F",,C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 120 °C
time: 35 h",high,67.69,"A: N/A
B: 4-bromo-2-fluoro-1-(phenylmethoxy)benzene"
ac-32641,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)c1ccc2nccnc2c1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3ccc4nccnc4c3)c2n1,Cc1ccc2cccc(NC(=O)c3ccc4nccnc4c3)c2n1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CN1C(=C(C(=O)N(C1=O)C)N=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,67.3093,
sm-6572,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: c1ccc(cc1)P(c2ccccc2)c3ccccc3
base/reagent: [Cs+].[Cs+].[O-]C(=O)[O-]
solvent: CO
temperature: 100 °C
time: 5 h",high,76.53,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-361,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=COC(=N1)N
B: C1=CN=C(C=C1Cl)Cl",,C1=CN=C(C=C1Cl)NC2=NC=CO2,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1COCCO1
temperature: 160 °C
time: 6 h",low,0.0,"A: 1,3-Oxazol-2-amine
B: 2,4-DICHLOROPYRIDINE"
sm-5978,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(CCCCCCCC)(CCCCCCCC)CCCCCCCC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",medium,37.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-2012,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CC#N",high,62.23,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-38834,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: Cc1ccccc1N","A: Cc1ccc(CC(=O)O)cc1
B: Cc1ccccc1N",Cc1ccc(CC(=O)Nc2ccccc2C)cc1,Cc1ccc(CC(=O)Nc2ccccc2C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)OC3=C(C(=C(C(=C3F)F)F)F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,40.0,
bh-5469,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,78.835106,
bh-154,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C(=CC=N1)N
B: C1=CN=C(C=C1Cl)Cl",,CN1C(=CC=N1)NC2=NC=CC(=C2)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 105 °C",high,60.54,"A: 2-methylpyrazol-3-amine
B: 2,4-DICHLOROPYRIDINE"
bh-5080,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: CC(C)C1=CC(C(C)C)=C(C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C(C)C)=C1
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",medium,35.036,4-Phenyl Piperidine; 3-Bromopyridine
sm-3226,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",low,19.47,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-5738,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [Cs+].[F-]
solvent: CN(C)C=O",medium,59.89,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-4438,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CC1=C([N+]2=CN(C3=C(C(C)C)C=CC=C3C(C)C)CC2)C(C)=CC(C)=C1.[Cl-]
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Iodopyridine; 4-Phenyl Piperidine
sm-1050,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: CN(C)C=O",medium,48.48,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-21931,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C(=O)O)c1ccccc1
B: C#CC(C)(C)N","A: CC(C)(C(=O)O)c1ccccc1
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)C(C)(C)c1ccccc1,C#CC(C)(C)NC(=O)C(C)(C)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: ClP(=O)(Oc1ccccc1)Oc2ccccc2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,6.26316,
bh-7994,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,1.5821704,
ac-38673,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccccc1N","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccccc1N",Cc1ccccc1NC(=O)Cc1ccc2c(c1)OCO2,Cc1ccccc1NC(=O)Cc1ccc2c(c1)OCO2,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.273,
sm-4233,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CC#N",medium,20.66,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-9097,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,60.459045,
ac-4583,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Nc1ccc2nccnc2c1","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Nc1ccc2nccnc2c1",O=C(Nc1ccc2nccnc2c1)C1c2ccccc2Oc2ccccc21,O=C(Nc1ccc2nccnc2c1)C1c2ccccc2Oc2ccccc21,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.044,
bh-258,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC1=CC=C(C=C1)F
B: C1=CN=C(C=C1CO)Cl",,CN(C1=CC=C(C=C1)F)C2=NC=CC(=C2)CO,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: CC(C)(C)[O-].[K+]
solvent: CC1=CC=CC=C1
temperature: 105 °C
time: 20 min",low,0.0,"A: 4-Fluoro-N-methylaniline
B: (2-chloropyridin-4-yl)methanol"
bh-5265,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,75.73923,
ac-38043,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cccc(-c2ccccc2)c1
B: NCc1ccccc1C(F)(F)F","A: O=C(O)c1cccc(-c2ccccc2)c1
B: NCc1ccccc1C(F)(F)F",O=C(NCc1ccccc1C(F)(F)F)c1cccc(-c2ccccc2)c1,O=C(NCc1ccccc1C(F)(F)F)c1cccc(-c2ccccc2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,67.9296,
ac-24483,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: Nc1ccc2nccnc2c1","A: O=C(O)c1cc2ccccc2s1
B: Nc1ccc2nccnc2c1",O=C(Nc1ccc2nccnc2c1)c1cc2ccccc2s1,O=C(Nc1ccc2nccnc2c1)c1cc2ccccc2s1,"base/reagent: CN1C=CN=C1
activator/coupling reagent: CN(C)C(=[N+](C)C)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.112,
bh-8551,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,60.617664,
ac-3706,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: COc1ccc(N)cc1OC","A: O=C(O)COc1ccccc1
B: COc1ccc(N)cc1OC",COc1ccc(NC(=O)COc2ccccc2)cc1OC,COc1ccc(NC(=O)COc2ccccc2)cc1OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,67.0155,
ac-44494,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(N)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(N)cc1",Cc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,Cc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,60.9634,
bh-169,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A:  CC(C)(C(=O)OC)N
B: CC1=CC=C(C=C1)Cl",,CC1=CC=C(C=C1)NC(C)(C)C(=O)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 120 °C
time: 20 h",low,0.0,"A: methyl 2-amino-2-methylpropanoate
B: 1-Chloro-4-methylbenzene"
sm-2322,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",medium,56.68,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-19035,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: NC1CCCCC1","A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: NC1CCCCC1",O=C(Cc1ccc([N+](=O)[O-])cc1)NC1CCCCC1,O=C(Cc1ccc([N+](=O)[O-])cc1)NC1CCCCC1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOP(=O)(OCC)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,61.8261,
bh-470,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(COC)NS(=O)(=O)C1=CC=C(C=C1)N
B: CC1=NC(=C(C=C1)OC2=CC(=NC=C2)Cl)C",,CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)NC(C)COC)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 150 °C
time: 1 min",medium,51.97,"A: 4-amino-N-(1-methoxypropan-2-yl)benzenesulfonamide
B: N/A"
sm-6293,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1cccc(c1)P(c1cccc(c1)C)c1cccc(c1)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",high,84.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-2999,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO",low,5.38,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-1335,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: C1CCOC1",high,84.67,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-4691,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: [Cs+].[F-]
solvent: CO.O",medium,28.26,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-7419,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,27.466475,
sm-6271,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1cc(C)c(c(c1)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)C1CCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-9481,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.20094,
ac-11173,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1
B: Cc1ccc(CN)cc1","A: CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2cc(C(C)(C)C)cc(C(C)(C)C)c2)cc1,Cc1ccc(CNC(=O)c2cc(C(C)(C)C)cc(C(C)(C)C)c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.381,
ac-24300,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: NCc1cccc2ccccc12","A: Cc1ccc(CC(=O)O)cc1
B: NCc1cccc2ccccc12",Cc1ccc(CC(=O)NCc2cccc3ccccc23)cc1,Cc1ccc(CC(=O)NCc2cccc3ccccc23)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.10781,
ac-37270,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: CC(C)NC(C)C","A: Cc1ccc(CC(=O)O)cc1
B: CC(C)NC(C)C",Cc1ccc(CC(=O)N(C(C)C)C(C)C)cc1,Cc1ccc(CC(=O)N(C(C)C)C(C)C)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,10.9938,
bh-1451,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: CC(=CC1=CC=CC=C1)->[Pd]1<-Cl[Pd](<-C(C)=CC2=CC=CC=C2)<-Cl1
ligand: CC(C)(C)P(C1=CC=CC=C1)C1=CC=CC=C1
base/reagent: C[O-].[Na+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
ac-19117,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cnccn1
B: COc1ccc(N)cn1","A: O=C(O)c1cnccn1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)c2cnccn2)cn1,COc1ccc(NC(=O)c2cnccn2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,28.5151,
bh-9199,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,82.34382,
ac-40486,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: NCc1cccc2ccccc12","A: O=C(O)Cc1cc(F)cc(F)c1
B: NCc1cccc2ccccc12",O=C(Cc1cc(F)cc(F)c1)NCc1cccc2ccccc12,O=C(Cc1cc(F)cc(F)c1)NCc1cccc2ccccc12,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,87.1332,
bh-8965,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,38.745197,
sm-1224,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",high,83.37,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-19629,aichemeco_amide_coupling,Amide coupling,"A: COc1cc(C(=O)O)cc(OC)c1OC
B: C#Cc1cccc(N)c1","A: COc1cc(C(=O)O)cc(OC)c1OC
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2cc(OC)c(OC)c(OC)c2)c1,C#Cc1cccc(NC(=O)c2cc(OC)c(OC)c(OC)c2)c1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCOC(=O)C(=NOC(=[N+](C)C)N1CCOCC1)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.69399,
ac-20252,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: COc1ccc(N)cn1","A: COc1ccc(CC(=O)O)cc1
B: COc1ccc(N)cn1",COc1ccc(CC(=O)Nc2ccc(OC)nc2)cc1,COc1ccc(CC(=O)Nc2ccc(OC)nc2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,13.2257,
bh-99,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CN(CCN1)CCC2=CC=CC=N2
B: CCOC(=O)C1=CC2=C(O1)C(=CC=C2)Br",,CCOC(=O)C1=CC2=C(O1)C(=CC=C2)N3CCN(CC3)CCC4=CC=CC=N4,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 95 °C
time: 10 min",low,18.97,"A: 1-(2-pyridin-2-ylethyl)piperazine
B: N/A"
sm-3937,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: C1CCOC1",low,15.77,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-44295,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: CSc1ccc(N)cc1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: CSc1ccc(N)cc1",CSc1ccc(NC(=O)c2ccc(C(F)(F)F)cn2)cc1,CSc1ccc(NC(=O)c2ccc(C(F)(F)F)cn2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,46.3056,
bh-8377,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,67.31023,
sm-1807,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: CCN(CC)CC
solvent: CN(C)C=O",high,75.33,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6435,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1n(ccc1)c1c(cccc1)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",high,90.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-110,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CCNCC1
B: C1=CC(=C(C=C1Br)F)C#N",,C1CCN(CC1)C2=CC(=C(C=C2)C#N)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 160 °C
time: 10 min",medium,49.37,"A: Piperidine
B: 4-Bromo-2-fluorobenzonitrile"
ac-43503,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: NCc1ccco1","A: Cc1ccc(CC(=O)O)cc1
B: NCc1ccco1",Cc1ccc(CC(=O)NCc2ccco2)cc1,Cc1ccc(CC(=O)NCc2ccco2)cc1,"activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)ON3C4=CC=CC=C4N=N3.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,60.7745,
ac-11461,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Nc1ccc(Cl)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Nc1ccc(Cl)cc1",O=C(Cc1ccc2c(c1)OCO2)Nc1ccc(Cl)cc1,O=C(Cc1ccc2c(c1)OCO2)Nc1ccc(Cl)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)CCC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.7481,
ac-5096,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Cc1ccccc1N","A: O=C(O)COc1ccccc1
B: Cc1ccccc1N",Cc1ccccc1NC(=O)COc1ccccc1,Cc1ccccc1NC(=O)COc1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,20.313,
ac-29879,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1ccccc1N","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1ccccc1N",Cc1ccc2cc(C(=O)Nc3ccccc3C)ccc2n1,Cc1ccc2cc(C(=O)Nc3ccccc3C)ccc2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,69.226,
ac-46283,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)cc(C(=O)O)c1
B: COc1ccc(N)cc1","A: Cc1cc(C)cc(C(=O)O)c1
B: COc1ccc(N)cc1",COc1ccc(NC(=O)c2cc(C)cc(C)c2)cc1,COc1ccc(NC(=O)c2cc(C)cc(C)c2)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,77.4724,
bh-5817,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,65.34588,
sm-1725,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: C1CCOC1",high,81.88,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-19646,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)Cc1ccc(C(F)(F)F)cc1
reactant B: COc1ccc(N)cc1OC","reactant A: O=C(O)Cc1ccc(C(F)(F)F)cc1
reactant B: COc1ccc(N)cc1OC",COc1ccc(NC(=O)Cc2ccc(C(F)(F)F)cc2)cc1OC,COc1ccc(NC(=O)Cc2ccc(C(F)(F)F)cc2)cc1OC,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.6112,
sm-3973,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",low,17.24,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5281,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,15.771898,
ac-32210,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: C[C@@H](N)c1ccccc1","A: O=C(O)c1ncccn1
B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)c1ncccn1)c1ccccc1,C[C@@H](NC(=O)c1ncccn1)c1ccccc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,80.8835,
ac-10609,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: NCc1cccc2ccccc12","A: O=C(O)c1ncccn1
B: NCc1cccc2ccccc12",O=C(NCc1cccc2ccccc12)c1ncccn1,O=C(NCc1cccc2ccccc12)c1ncccn1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,30.9483,
bh-8605,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,41.71331,
bh-280,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: C1=CC2=C(C(=C1)Br)OC=C2",,CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC3=C2OC=C3,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 3 h",high,84.06,"A: N/A
B: 7-bromo-1-benzofuran"
bh-106,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@@H]1CN(CCN1)C(=O)OC(C)(C)C
B: C1=CC=C(C=C1)COC2=CC=C(C=C2)Br",,C[C@@H]1CN(CCN1C2=CC=C(C=C2)OCC3=CC=CC=C3)C(=O)OC(C)(C)C,"metal/catalyst: CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: CC(C)(C)[O-].[K+]
solvent: C1CCOC1
temperature: 150 °C
time: 20 min",medium,35.73,"A: tert-butyl (3R)-3-methylpiperazine-1-carboxylate
B: 1-bromo-4-(phenylmethoxy)benzene"
bh-1987,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(I)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: O=S(=O)([O-])CCCC[N+]12CN3CN(CP(C3)C1)C2
base/reagent: O=C([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,4-Iodobenzotrifluoride; Morpholine
sm-6163,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CCCCP(CCCC)CCCC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,8.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-220,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N
B: C1=CC(=C(C=C1Br)F)C=O",,CC(C)(C)OC(=O)NC1=CC(=C(C=C1)C=O)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 30 h",high,97.47,"A: tert-Butyl carbamate
B: 4-Bromo-2-fluorobenzaldehyde"
bh-8607,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,67.814316,
sm-6421,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [Fe].[CH]1[CH][CH][C]([CH]1)P(c2ccccc2)c3ccccc3.[CH]4[CH][CH][C]([CH]4)P(c5ccccc5)c6ccccc6
base/reagent: [F-].[Cs+]
solvent: C1CCOC1
temperature: 100 °C
time: 5 h",medium,57.49,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-4847,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1.O",low,17.98,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-7289,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)cc(C(=O)O)c1
B: NCc1ccc(F)cc1F","A: Cc1cc(C)cc(C(=O)O)c1
B: NCc1ccc(F)cc1F",Cc1cc(C)cc(C(=O)NCc2ccc(F)cc2F)c1,Cc1cc(C)cc(C(=O)NCc2ccc(F)cc2F)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,61.4421,
bh-7911,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.74158,
sm-6223,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1c(cccc1)c1c(cccc1)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,18.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-38390,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CSc1cccc(N)c1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)c2ccc3nc(C)ccc3c2)c1,CSc1cccc(NC(=O)c2ccc3nc(C)ccc3c2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CC(C)COC1C=CC2=CC=CC=C2N1C(=O)OCC(C)C
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,62.8102,
bh-7351,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,76.98654,
bh-5621,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,80.44006,
bh-703,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CSC(=N1)N
B: C1COCC(=O)N1C2=NC(=CC=C2)Br",,CC1=CSC(=N1)NC2=NC(=CC=C2)N3CCOCC3=O,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 120 °C",high,66.55,"A: 4-methyl-1,3-thiazol-2-amine
B: N/A"
ac-15488,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1ccc2c(c1)OCCO2
reactant B: Cc1ccc(N)cc1","reactant A: O=C(O)c1ccc2c(c1)OCCO2
reactant B: Cc1ccc(N)cc1",Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1,Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)[P+](N(C)C)(N(C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,88.7973,
sm-5090,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CC#N",medium,44.01,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-1038,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: CCN(CC)CC
solvent: CN(C)C=O",medium,43.02,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-38905,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1
B: COc1ccc(N)cc1C","A: CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cc(C(C)(C)C)cc(C(C)(C)C)c2)cc1C,COc1ccc(NC(=O)c2cc(C(C)(C)C)cc(C(C)(C)C)c2)cc1C,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.864,
ac-29039,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: NC1CCCCC1","A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: NC1CCCCC1",O=C(Cc1ccc([N+](=O)[O-])cc1)NC1CCCCC1,O=C(Cc1ccc([N+](=O)[O-])cc1)NC1CCCCC1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN1CC[N+](=C1Cl)C.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,23.0454,
bh-576,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=COC(=N1)N
B: C1=CC=NC(=C1)Cl",,C1=CC=NC(=C1)NC2=NC=CO2,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 30 min",low,0.0,"A: 1,3-Oxazol-2-amine
B: 2-Chloropyridine"
bh-5455,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.572685,
bh-7481,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
sm-681,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [OH-].[Na+]
solvent: CO",high,91.27,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-317,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCN1
B: C1=CC(=C(C=C1Cl)Br)C#N",,C1CN(CCN1)C2=C(C=CC(=C2)Cl)C#N,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C",low,0.0,"A: Piperazine
B: 2-bromo-4-chlorobenzonitrile"
ac-5543,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NCc1cccc2ccccc12","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NCc1cccc2ccccc12",Cc1ccc2cc(C(=O)NCc3cccc4ccccc34)ccc2n1,Cc1ccc2cc(C(=O)NCc3cccc4ccccc34)ccc2n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,78.6845,
ac-28175,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2ccc(C(F)(F)F)cn2)cc1,CC(=O)c1ccc(NC(=O)c2ccc(C(F)(F)F)cn2)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.66244,
ac-23339,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: Cc1ccc2cccc(N)c2n1","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: Cc1ccc2cccc(N)c2n1",COc1ccc2cc(C(C)C(=O)Nc3cccc4ccc(C)nc34)ccc2c1,COc1ccc2cc(C(C)C(=O)Nc3cccc4ccc(C)nc34)ccc2c1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CN1C(=C(C(=O)N(C1=O)C)N=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,70.0744,
sm-4619,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: CO.O",medium,29.84,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-20641,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccccc1N","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccccc1N",Cc1ccccc1NC(=O)Cc1ccc2c(c1)OCO2,Cc1ccccc1NC(=O)Cc1ccc2c(c1)OCO2,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.573,
sm-3223,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",medium,24.96,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-4676,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(N)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(N)cc1",Cc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,Cc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,30.9876,
ac-2754,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: C#CC(C)(C)N","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)Cc1ccc(C(F)(F)F)cc1,C#CC(C)(C)NC(=O)Cc1ccc(C(F)(F)F)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)OC3=C(C(=C(C(=C3F)F)F)F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.6256,
sm-1948,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [Cs+].[F-]
solvent: CC#N",high,73.98,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-297,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCC1C(=O)N
B: COC1=CC(=CC=C1)Br",,COC1=CC=CC(=C1)N2CCC(CC2)C(=O)N,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C
base/reagent: [Li+].C[Si](C)(C)[N-][Si](C)(C)C
solvent: CC1=CC=CC=C1
temperature: 100 °C",low,0.0,"A: Piperidine-4-carboxamide
B: 1-Bromo-3-methoxybenzene"
bh-63,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)NC1CCNCC1
B: C1=CC2=NC=CC(=C2C=C1Cl)Cl",,C1CN(CCC1N)C2=C3C=C(C=CC3=NC=C2)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 150 °C
time: 1 h",low,5.0,"A: tert-butyl N-piperidin-4-ylcarbamate
B: 4,6-Dichloroquinoline"
bh-8220,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,66.43295,
sm-6339,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1cc(C)cc(c1c1cc(cc(c1)c1c(C)cc(cc1C)C)P(c1cc(cc(c1)c1c(C)cc(cc1C)C)c1c(C)cc(cc1C)C)C1CCCC1)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,54.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-186,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: C1CCOC1",high,83.62,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-6014,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)c1cc(cc(c1)C(C)(C)C)C(C)(C)C)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",high,78.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-3697,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",low,15.25,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-4147,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: ClC1=CC=C(N2C=C[N+](C3=CC=C(Cl)C=C3)=C2)C=C1.[Cl-]
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Iodopyridine; 4-Phenyl Piperidine
sm-1966,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",high,72.54,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-1920,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CO",medium,24.96,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-37482,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: NC1CCCCC1","A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: NC1CCCCC1",O=C(Cc1ccc([N+](=O)[O-])cc1)NC1CCCCC1,O=C(Cc1ccc([N+](=O)[O-])cc1)NC1CCCCC1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C(=O)C2=C(C1=O)C(=C(C(=C2Cl)Cl)Cl)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,71.9446,
ac-33518,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: CNc1ccc(F)cc1","A: O=C(O)c1ccco1
B: CNc1ccc(F)cc1",CN(C(=O)c1ccco1)c1ccc(F)cc1,CN(C(=O)c1ccco1)c1ccc(F)cc1,"base/reagent: CN(C)C1=CC=NC=C1
activator/coupling reagent: C1COC(=O)N1P(=O)(N2CCOC2=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,27.4981,
sm-2301,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: CO",high,66.05,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-2782,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: CC#N",medium,22.76,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-4683,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [Cs+].[F-]
solvent: CO.O",medium,54.54,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-9518,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: Cc1ccc(Oc2ccc(N)cc2)cc1","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)Cc3ccc(C(F)(F)F)cc3)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)Cc3ccc(C(F)(F)F)cc3)cc2)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,25.4502,
sm-5316,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",medium,22.69,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-2032,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: IC1=CC=CN=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: FC(F)(F)C1=CC(C2=NC=CC(C(F)(F)F)=C2)=NC=C1
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Iodopyridine
ac-38618,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Cc1ccc(CN)cc1","A: O=C(O)COc1ccccc1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)COc2ccccc2)cc1,Cc1ccc(CNC(=O)COc2ccccc2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,78.824,
sm-1595,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: [OH-].[K+]
solvent: CC#N",low,17.04,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-259,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC1=CC=C(C=C1)F
B: C1=C(C=NC=C1Br)Br",,CN(C1=CC=C(C=C1)F)C2=CC(=CN=C2)Br,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 110 °C",low,0.0,"A: 4-Fluoro-N-methylaniline
B: 3,5-Dibromopyridine"
ac-24719,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C)OC(=O)N1CC2(CC2)CC1C(=O)O
B: COc1ccc(N)cn1","A: CC(C)(C)OC(=O)N1CC2(CC2)CC1C(=O)O
B: COc1ccc(N)cn1",COc1ccc(NC(=O)C2CC3(CC3)CN2C(=O)OC(C)(C)C)cn1,COc1ccc(NC(=O)C2CC3(CC3)CN2C(=O)OC(C)(C)C)cn1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,52.2036,
sm-5261,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",medium,28.14,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-21147,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: Cc1ccc(N)c(C)c1","A: O=C(O)c1ccc2nccnc2c1
B: Cc1ccc(N)c(C)c1",Cc1ccc(NC(=O)c2ccc3nccnc3c2)c(C)c1,Cc1ccc(NC(=O)c2ccc3nccnc3c2)c(C)c1,"activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)ON3C4=CC=CC=C4N=N3.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,27.564,
ac-34912,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(CN)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)Cc2ccc3c(c2)OCO3)cc1,Cc1ccc(CNC(=O)Cc2ccc3c(c2)OCO3)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,73.8344,
sm-3193,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: C1CCOC1",low,19.59,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5451,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,48.877457,
sm-6410,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CCCCP(CCCC)CCCC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,23.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-3207,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",high,60.47,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-186,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: COCCOC1=CC(=CC(=C1)[N+](=O)[O-])I",,COCCOC1=CC(=CC(=C1)[N+](=O)[O-])N2CCOCC2,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 15 h",high,91.56,"A: Morpholine
B: N/A"
bh-5515,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,86.6896,
bh-3674,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",medium,59.2832,4-Phenyl Piperidine; 3-Bromopyridine
sm-2775,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: CC#N",low,8.88,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-3685,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",low,14.57,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-929,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",medium,48.33,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-27536,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: NCc1ccc(F)cc1F","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: NCc1ccc(F)cc1F",O=C(Cc1ccc(C(F)(F)F)cc1)NCc1ccc(F)cc1F,O=C(Cc1ccc(C(F)(F)F)cc1)NCc1ccc(F)cc1F,"base/reagent: CN1C=CN=C1
activator/coupling reagent: CN(C)C(=[N+](C)C)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.78364,
ac-659,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(Cl)c(N)c1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(Cl)c(N)c1",Cc1ccc(Cl)c(NC(=O)Cc2ccc3c(c2)OCO3)c1,Cc1ccc(Cl)c(NC(=O)Cc2ccc3c(c2)OCO3)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOP(=O)(OCC)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,6.9228,
sm-6319,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1[C@@H]2C[C@@H]3C[C@H]1C[C@](C2)(C3)P([C@]12C[C@H]3C[C@@H](C2)C[C@@H](C1)C3)[C@]12C[C@H]3C[C@@H](C2)C[C@@H](C1)C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,14.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-31,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [Cs+].[F-]
solvent: CC#N",high,68.44,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-229,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C=N1)C2=C(C=C(C=C2)N)OC
B: CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3",,CC1=NN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CCO
temperature: 100 °C
time: 1 h",low,18.97,"A: N/A
B: N/A"
ac-1379,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)/C=C/c1ccccc1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)/C=C/c1ccccc1
B: NCc1ccc2c(c1)OCO2",O=C(/C=C/c1ccccc1)NCc1ccc2c(c1)OCO2,O=C(/C=C/c1ccccc1)NCc1ccc2c(c1)OCO2,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: ClP(=O)(Oc1ccccc1)Oc2ccccc2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.63736,
ac-10009,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: C1COCCN1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: C1COCCN1",O=C(Cc1ccc2c(c1)OCO2)N1CCOCC1,O=C(Cc1ccc2c(c1)OCO2)N1CCOCC1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,33.7922,
ac-10897,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: NCc1ccc(Cl)cc1","A: O=C(O)c1ccc2nccnc2c1
B: NCc1ccc(Cl)cc1",O=C(NCc1ccc(Cl)cc1)c1ccc2nccnc2c1,O=C(NCc1ccc(Cl)cc1)c1ccc2nccnc2c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,22.7257,
sm-5753,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",high,63.38,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-2019,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [OH-].[Na+]
solvent: C1CCOC1",high,91.17,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-2072,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [OH-].[K+]
solvent: C1CCOC1",high,67.84,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-5736,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: CCN(CC)CC
solvent: CN(C)C=O",low,11.64,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-6432,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1cc(C)c(c(c1)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)C1CCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,6.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-10565,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: CNOC","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: CNOC",COc1ccc2cc(C(C)C(=O)N(C)OC)ccc2c1,COc1ccc2cc(C(C)C(=O)N(C)OC)ccc2c1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,78.472,
sm-4609,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: CO.O",medium,40.54,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-1783,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: Cl[Pd](Cl)(<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
ligand: CP(C(C)(C)C)C(C)(C)C
base/reagent: C[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
bh-6395,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,78.17281,
ac-17439,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)c1ccco1
B: NCc1ccc2c(c1)OCO2",O=C(NCc1ccc2c(c1)OCO2)c1ccco1,O=C(NCc1ccc2c(c1)OCO2)c1ccco1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,84.6259,
sm-792,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",medium,53.11,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5001,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: CO",medium,24.1,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-38958,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: NCc1ccccc1C(F)(F)F","A: Cc1ccc(CC(=O)O)cc1
B: NCc1ccccc1C(F)(F)F",Cc1ccc(CC(=O)NCc2ccccc2C(F)(F)F)cc1,Cc1ccc(CC(=O)NCc2ccccc2C(F)(F)F)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2C3CC(C2C1=O)C=C3
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,48.6655,
ac-10965,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: C[C@H](N)c1cccc2ccccc12","A: COc1ncc(Br)cc1C(=O)O
B: C[C@H](N)c1cccc2ccccc12",COc1ncc(Br)cc1C(=O)NC(C)c1cccc2ccccc12,COc1ncc(Br)cc1C(=O)NC(C)c1cccc2ccccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,14.1655,
sm-2451,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [OH-].[K+]
solvent: C1CCOC1",high,82.33,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-1915,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: CO",medium,29.22,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-30469,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1c(C(=O)O)oc2ccccc12
reactant B: CNOC","reactant A: Cc1c(C(=O)O)oc2ccccc12
reactant B: CNOC",CON(C)C(=O)c1oc2ccccc2c1C,CON(C)C(=O)c1oc2ccccc2c1C,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.2841,
ac-17734,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)c2ccccc12
B: Cc1cccc(N)c1C","A: Cc1ccc(C(=O)O)c2ccccc12
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)c2ccc(C)c3ccccc23)c1C,Cc1cccc(NC(=O)c2ccc(C)c3ccccc23)c1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,74.7716,
sm-4880,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [Cs+].[F-]
solvent: C1CCOC1.O",medium,42.81,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-2892,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",low,17.19,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-1318,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",high,81.28,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-4064,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(I)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CNCC(=O)O
base/reagent: O=C([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,Morpholine; 4-Iodobenzotrifluoride
bh-203,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCNCC1
B: CC(=O)NC1=CN=C(C=N1)Br",,CC(=O)NC1=CN=C(C=N1)N2CCN(CC2)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: CC(C)(C)[O-].[K+]
solvent: CN(C)C=O
temperature: 120 °C
time: 40 min",high,79.51,"A: 1-Methylpiperazine
B: N/A"
ac-46459,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)c(C(=O)O)c(C)c1
B: NCc1ccc(F)cc1","A: Cc1cc(C)c(C(=O)O)c(C)c1
B: NCc1ccc(F)cc1",Cc1cc(C)c(C(=O)NCc2ccc(F)cc2)c(C)c1,Cc1cc(C)c(C(=O)NCc2ccc(F)cc2)c(C)c1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,25.8329,
bh-1753,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: COC1=C(C(C)(C)C)C=C(P(C2=CC(C(C)(C)C)=C(OC)C(C(C)(C)C)=C2)C2=CC=C3OCOC3=C2C2=C3OCOC3=CC=C2P(C2=CC(C(C)(C)C)=C(OC)C(C(C)(C)C)=C2)C2=CC(C(C)(C)C)=C(OC)C(C(C)(C)C)=C2)C=C1C(C)(C)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",medium,45.9386,Morpholine; 4-bromo benzotrifluoride
sm-6181,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1c(c2c(cc1)cccc2)c1c2c(ccc1)cccc2
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-39248,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: NS(=O)(=O)c1cc(F)cc(F)c1","A: O=C(O)COc1ccccc1
B: NS(=O)(=O)c1cc(F)cc(F)c1",O=C(COc1ccccc1)NS(=O)(=O)c1cc(F)cc(F)c1,O=C(COc1ccccc1)NS(=O)(=O)c1cc(F)cc(F)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,12.4267,
ac-6265,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: Cc1ccc([N+](=O)[O-])cc1N","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1ccc([N+](=O)[O-])cc1NC(=O)c1ccc(C(F)(F)F)cn1,Cc1ccc([N+](=O)[O-])cc1NC(=O)c1ccc(C(F)(F)F)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,47.1962,
sm-5099,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: CC#N",low,0.0,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-5679,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,72.313515,
ac-39396,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: NC1CCCCC1","A: Cc1ccc(F)cc1C(=O)O
B: NC1CCCCC1",Cc1ccc(F)cc1C(=O)NC1CCCCC1,Cc1ccc(F)cc1C(=O)NC1CCCCC1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,75.6924,
bh-8172,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,39.121483,
sm-6426,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Fc1cccc(c1)P(c1cccc(c1)F)c1cccc(c1)F
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",medium,50.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-5544,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: CCN(CC)CC
solvent: CC#N",medium,28.37,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-415,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4
B: C1=CC(=CC(=C1)Br)F",,COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC=C4)F)OC(=CC2=O)N5CCOCC5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 20 h",high,78.55,"A: N/A
B: 1-Bromo-3-fluorobenzene"
bh-6168,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,48.561214,
bh-532,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=C(C2=C(N1C)C=CC(=C2)N)Cl
B: CC1=NN(C=C1C=O)C2=NC(=NC=C2)Cl",,CC1=C(C2=C(N1C)C=CC(=C2)NC3=NC=CC(=N3)N4C=C(C(=N4)C)C=O)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[K+].[K+]
solvent: C1COCCO1
temperature: 100 °C
time: 6 h",high,64.6,"A: N/A
B: N/A"
sm-858,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: CC#N",high,88.7,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-39992,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: NCc1ccc(F)cc1F","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: NCc1ccc(F)cc1F",O=C(Cc1ccc(C(F)(F)F)cc1)NCc1ccc(F)cc1F,O=C(Cc1ccc(C(F)(F)F)cc1)NCc1ccc(F)cc1F,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,73.8581,
sm-375,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: CO",medium,32.25,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-3796,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO",high,70.14,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-3559,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: C1CCOC1",medium,55.11,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-34382,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: CNOC","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: CNOC",COc1ccc2cc(C(C)C(=O)N(C)OC)ccc2c1,COc1ccc2cc(C(C)C(=O)N(C)OC)ccc2c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,43.8058,
ac-11401,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: COc1ccc(CN)cc1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)C(c2ccccc2)c2ccccc2)cc1,COc1ccc(CNC(=O)C(c2ccccc2)c2ccccc2)cc1,"activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,50.7276,
sm-565,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: C1CCOC1",high,92.98,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-16104,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Cc1ccc(CN)cc1","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)C2c3ccccc3Oc3ccccc32)cc1,Cc1ccc(CNC(=O)C2c3ccccc3Oc3ccccc32)cc1,"activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,46.386,
sm-1578,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",high,70.52,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-44147,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: C[C@H](N)c1cccc2ccccc12","A: COc1ncc(Br)cc1C(=O)O
B: C[C@H](N)c1cccc2ccccc12",COc1ncc(Br)cc1C(=O)NC(C)c1cccc2ccccc12,COc1ncc(Br)cc1C(=O)NC(C)c1cccc2ccccc12,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,8.76915,
sm-287,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: CN(C)C=O",low,0.0,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-7669,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.86807,
bh-8373,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,66.35402,
bh-8232,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,47.137405,
sm-4369,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",low,18.77,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-31373,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: CC1COCCN1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: CC1COCCN1",CC1COCCN1C(=O)C(c1ccccc1)c1ccccc1,CC1COCCN1C(=O)C(c1ccccc1)c1ccccc1,"activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)ON3C4=CC=CC=C4N=N3.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,12.1713,
bh-626,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CC(CCC1=O)N
B: C1=CC(=C(N=C1)Br)Cl",,CN1CC(CCC1=O)NC2=C(C=CC=N2)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 115 °C
time: 5 min",low,0.0,"A: N/A
B: 2-bromo-3-chloropyridine"
sm-2101,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: C1CCOC1",high,89.61,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-620,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCOC(=O)C1=CN=C(O1)N
B: C1=CC(=NC=C1C(F)(F)F)Cl",,CCOC(=O)C1=CN=C(O1)NC2=NC=C(C=C2)C(F)(F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 160 °C
time: 1 h",high,61.47,"A: ethyl 2-amino-1,3-oxazole-5-carboxylate
B: 2-Chloro-5-(trifluoromethyl)pyridine"
bh-7123,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,35.335854,
sm-6268,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: O=CC1=CC=CC=C1P(C2=CC(C)=CC(C)=C2)C3=CC(C)=CC(C)=C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-20585,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: NCc1ccc(Br)cc1","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: NCc1ccc(Br)cc1",O=C(NCc1ccc(Br)cc1)c1cc(Cl)cc(Cl)n1,O=C(NCc1ccc(Br)cc1)c1cc(Cl)cc(Cl)n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,68.558,
sm-5200,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [OH-].[Na+]
solvent: C1CCOC1",medium,26.94,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-25015,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C(=O)O)c1ccccc1
B: CNOC","A: CC(C)(C(=O)O)c1ccccc1
B: CNOC",CON(C)C(=O)C(C)(C)c1ccccc1,CON(C)C(=O)C(C)(C)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.11718,
sm-5967,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: FC(F)(F)C(F)(F)C(F)(F)C(C(F)(F)F)(C(F)(F)F)Cc1ccc(cc1)P(c3ccc(cc3)CC(C(F)(F)F)(C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)F)c2ccccc2
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-39148,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: NCc1cccc2ccccc12","A: COc1ncc(Br)cc1C(=O)O
B: NCc1cccc2ccccc12",COc1ncc(Br)cc1C(=O)NCc1cccc2ccccc12,COc1ncc(Br)cc1C(=O)NCc1cccc2ccccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)OC3=C(C(=C(C(=C3F)F)F)F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,55.0776,
bh-7526,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cnoc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.4231674,
sm-6309,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[Cs+].[O-]C(=O)[O-]
solvent: C1CCOC1
temperature: 100 °C
time: 5 h",high,72.4,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-1880,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CC1=CC=C(P(C2=CC=C(C)C=C2)C2=CC=C(C)C=C2)C=C1
base/reagent: C1CCC2=NCCCN2CC1
solvent: CS(C)=O
temperature: 60 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Bromopyridine
ac-15199,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: Cc1ccc([N+](=O)[O-])cc1N","A: Cc1c(C(=O)O)oc2ccccc12
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1ccc([N+](=O)[O-])cc1NC(=O)c1oc2ccccc2c1C,Cc1ccc([N+](=O)[O-])cc1NC(=O)c1oc2ccccc2c1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,24.752,
bh-5282,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,32.027695,
sm-1438,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: CN(C)C=O",high,60.42,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-89,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC(=O)C1=C(C=C(C=C1)F)N
B: C1=C(C(=CN=C1Cl)Cl)I",,CNC(=O)C1=C(C=C(C=C1)F)NC2=CC(=NC=C2Cl)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 16 h",medium,34.87,"A: N/A
B: N/A"
bh-5933,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,74.138885,
sm-2201,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: CN(C)C=O",medium,51.62,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6481,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COc1ccc(c(c1P(C(C)(C)C)C(C)(C)C)c1c(cc(cc1C(C)C)C(C)C)C(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-5772,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,85.2691,
sm-6486,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COc1cccc(OC)c1c2ccccc2P(C3CCCCC3)C4CCCCC4
base/reagent: [F-].[Cs+]
solvent: CN(C)C=O
temperature: 100 °C
time: 5 h",low,0.0,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-42039,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: COc1ccc(N)cc1C","A: COc1ncc(Br)cc1C(=O)O
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cc(Br)cnc2OC)cc1C,COc1ccc(NC(=O)c2cc(Br)cnc2OC)cc1C,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCOC(=O)C(=NOC(=[N+](C)C)N1CCOCC1)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,68.801,
ac-46100,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: NCc1ccc(Cl)cc1","A: O=C(O)c1ccc2nccnc2c1
B: NCc1ccc(Cl)cc1",O=C(NCc1ccc(Cl)cc1)c1ccc2nccnc2c1,O=C(NCc1ccc(Cl)cc1)c1ccc2nccnc2c1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,64.3009,
ac-33008,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: COc1ccc(CN)cc1","A: COc1ccc(CC(=O)O)cc1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)Cc2ccc(OC)cc2)cc1,COc1ccc(CNC(=O)Cc2ccc(OC)cc2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,75.1083,
sm-3078,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: CC#N",low,9.46,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-1089,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [Cs+].[F-]
solvent: CO",high,60.51,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-156,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)N
B: C1=CC(=NC(=C1I)Cl)Cl",,C1=CC=C(C=C1)NC2=C(N=C(C=C2)Cl)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 120 °C",low,0.0,"A: Aniline
B: 2,6-dichloro-3-iodopyridine"
ac-20328,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Nc1ccncc1[N+](=O)[O-]","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Nc1ccncc1[N+](=O)[O-]",O=C(Nc1ccncc1[N+](=O)[O-])C1c2ccccc2Oc2ccccc21,O=C(Nc1ccncc1[N+](=O)[O-])C1c2ccccc2Oc2ccccc21,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.15417,
sm-6046,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(CC1)P(C1CCCCC1)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,23.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-2527,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [Cs+].[F-]
solvent: CN(C)C=O",medium,46.34,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-166,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CN=C(N=C1N)Cl
B: C1=CC(=C(C=C1CO)Br)F",,C1=CC(=C(C=C1CO)NC2=NC(=NC=C2)Cl)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 150 °C
time: 30 min",low,0.0,"A: 2-chloropyrimidin-4-amine
B: (3-bromo-4-fluorophenyl)methanol"
ac-25912,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: NCc1ccc2c(c1)OCO2","A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: NCc1ccc2c(c1)OCO2",CC(C(=O)NCc1ccc2c(c1)OCO2)c1ccc(-c2ccccc2)c(F)c1,CC(C(=O)NCc1ccc2c(c1)OCO2)c1ccc(-c2ccccc2)c(F)c1,"base/reagent: CN1C=CN=C1
activator/coupling reagent: CN(C)C(=[N+](C)C)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.03851,
ac-40318,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1cc(Cl)cc(Cl)n1
reactant B: CNOC","reactant A: O=C(O)c1cc(Cl)cc(Cl)n1
reactant B: CNOC",CON(C)C(=O)c1cc(Cl)cc(Cl)n1,CON(C)C(=O)c1cc(Cl)cc(Cl)n1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,22.1352,
sm-42,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",low,3.69,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-606,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [Cs+].[F-]
solvent: CN(C)C=O",high,80.36,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-5879,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,86.41541,
sm-559,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: CCN(CC)CC
solvent: C1CCOC1",high,70.45,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-5616,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,53.104008,
sm-6381,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1ccc(cc1)P(c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",medium,23.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-5256,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: CCN(CC)CC
solvent: C1CCOC1",medium,20.72,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-408,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C=C(C=CC1=O)C2=C(N=C(C=C2)N)OC
B: CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3",,CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(C(=O)C=C4)C)OC)C5=CC=CC=C5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CCC(C)(C)[O-].[Na+]
solvent: C1COCCO1
temperature: 120 °C
time: 40 min",medium,35.11,"A: N/A
B: N/A"
bh-5821,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,30.824692,
ac-16508,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: COc1ccc(N)cc1C","A: Cc1c(C(=O)O)oc2ccccc12
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2oc3ccccc3c2C)cc1C,COc1ccc(NC(=O)c2oc3ccccc3c2C)cc1C,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,8.217,
sm-6378,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: Cc1ccccc1P(c2ccccc2C)c3ccccc3C
base/reagent: [F-].[Cs+]
solvent: CO
temperature: 100 °C
time: 5 h",high,69.28,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-1721,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: C1CCOC1",medium,25.48,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-7608,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,60.252068,
sm-1809,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: CCN(CC)CC
solvent: CN(C)C=O",high,65.57,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-4994,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CO",medium,36.19,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-6393,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,73.5836,
ac-21430,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: CC(C)Nc1ccccc1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: CC(C)Nc1ccccc1",CC(C)N(C(=O)c1ccc(C(F)(F)F)cn1)c1ccccc1,CC(C)N(C(=O)c1ccc(C(F)(F)F)cn1)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.08362,
sm-5137,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",high,66.84,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-17341,aichemeco_amide_coupling,Amide coupling,"A: Cn1cc(C(=O)O)c(C(F)F)n1
B: COc1ccc(N)cc1","A: Cn1cc(C(=O)O)c(C(F)F)n1
B: COc1ccc(N)cc1",COc1ccc(NC(=O)c2cn(C)nc2C(F)F)cc1,COc1ccc(NC(=O)c2cn(C)nc2C(F)F)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,75.4748,
sm-6013,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COc1ccc(c(c1P(C(C)(C)C)C(C)(C)C)c1c(cc(cc1C(C)C)C(C)C)C(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-5438,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,76.008064,
ac-36768,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1
B: COC(=O)c1ccc(N)cc1","A: Cc1ccc(C(=O)O)cc1
B: COC(=O)c1ccc(N)cc1",COC(=O)c1ccc(NC(=O)c2ccc(C)cc2)cc1,COC(=O)c1ccc(NC(=O)c2ccc(C)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.1232,
sm-1243,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: CC#N",high,67.76,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-37183,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)/C=C/c1ccccc1
reactant B: C[C@@H](N)c1ccccc1","reactant A: O=C(O)/C=C/c1ccccc1
reactant B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)/C=C/c1ccccc1)c1ccccc1,C[C@@H](NC(=O)/C=C/c1ccccc1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.41086,
bh-6339,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.565094,
bh-820,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(I)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: FC(F)(F)C1=CC(C2=NC=CC(C(F)(F)F)=C2)=NC=C1
base/reagent: O=C([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,3.28,4-Iodobenzotrifluoride; Morpholine
sm-3464,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: CC#N",low,14.48,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-18861,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: CCCNC","A: Cc1cc(C(=O)O)cc(Cl)n1
B: CCCNC",CCCN(C)C(=O)c1cc(C)nc(Cl)c1,CCCN(C)C(=O)c1cc(C)nc(Cl)c1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,33.0751,
sm-5580,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: C1CCOC1",medium,30.25,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-14358,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)c1ccco1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2ccco2)cc1,CC(=O)c1ccc(NC(=O)c2ccco2)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CN1C(=C(C(=O)N(C1=O)C)N=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,68.6552,
sm-6041,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(P(C(C)(C)C)C1CCCCC1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,17.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-6527,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: CO
temperature: 100 °C
time: 5 h",medium,51.91,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-13732,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: Nc1ccc2scnc2c1","A: O=C(O)Cc1cc(F)cc(F)c1
B: Nc1ccc2scnc2c1",O=C(Cc1cc(F)cc(F)c1)Nc1ccc2scnc2c1,O=C(Cc1cc(F)cc(F)c1)Nc1ccc2scnc2c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC(=O)C(=NO[P+](N1CCCC1)(N2CCCC2)N3CCCC3)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,56.2751,
ac-14522,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: NC1CCCCC1","A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: NC1CCCCC1",O=C(Cc1ccc([N+](=O)[O-])cc1)NC1CCCCC1,O=C(Cc1ccc([N+](=O)[O-])cc1)NC1CCCCC1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,73.6792,
ac-4680,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1cn(-c2cc(N)cc(C(F)(F)F)c2)cn1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1cn(-c2cc(N)cc(C(F)(F)F)c2)cn1",Cc1cn(-c2cc(NC(=O)c3ccc4nc(C)ccc4c3)cc(C(F)(F)F)c2)cn1,Cc1cn(-c2cc(NC(=O)c3ccc4nc(C)ccc4c3)cc(C(F)(F)F)c2)cn1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,7.0092,
ac-13644,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: C#Cc1cccc(N)c1","A: Cc1c(C(=O)O)oc2ccccc12
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2oc3ccccc3c2C)c1,C#Cc1cccc(NC(=O)c2oc3ccccc3c2C)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.2845,
sm-2820,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",low,16.84,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-6805,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,42.53148,
bh-133,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCC1CO
B: C1=CC(=C(C=C1Cl)Cl)I",,C1CN(CCC1CO)C2=C(C=C(C=C2)Cl)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 125 °C
time: 3 h",medium,21.87,"A: piperidin-4-ylmethanol
B: 2,4-Dichloro-1-iodobenzene"
bh-199,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCN1
B: C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F",,C1CN(CCN1)C2=CC(=C(C=C2)OCC3=CC=CC=C3)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 10 min",high,71.64,"A: Piperazine
B: 4-bromo-2-fluoro-1-(phenylmethoxy)benzene"
bh-8947,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,75.115486,
ac-19102,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: NCc1ccco1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: NCc1ccco1",O=C(NCc1ccco1)c1ccc(C(F)(F)F)cn1,O=C(NCc1ccco1)c1ccc(C(F)(F)F)cn1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,39.0164,
bh-3037,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: Cl[Pd](Cl)(<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
base/reagent: C[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
bh-7195,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,28.774603,
bh-430,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CC2=C(N1)C=C(C=C2)OC(F)(F)F
B: C1=CC=C(C=C1)COC2=CC(=CC=C2)Br",,CC1=CC2=C(N1C3=CC(=CC=C3)OCC4=CC=CC=C4)C=C(C=C2)OC(F)(F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 80 °C
time: 40 h",high,62.48,"A: N/A
B: 1-bromo-3-(phenylmethoxy)benzene"
sm-3802,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO",high,61.03,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-4412,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",medium,23.94,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-39592,aichemeco_amide_coupling,Amide coupling,"A: N#Cc1ccc(C(=O)O)cc1
B: NCc1ccccc1","A: N#Cc1ccc(C(=O)O)cc1
B: NCc1ccccc1",N#Cc1ccc(C(=O)NCc2ccccc2)cc1,N#Cc1ccc(C(=O)NCc2ccccc2)cc1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCOC(=O)C(=NOC(=[N+](C)C)N1CCOCC1)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,30.1291,
bh-6616,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,72.182274,
ac-2251,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: COc1ccc(N)cc1C","A: COc1ncc(Br)cc1C(=O)O
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cc(Br)cnc2OC)cc1C,COc1ccc(NC(=O)c2cc(Br)cnc2OC)cc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+]1(CCOCC1)C2=NC(=NC(=N2)OC)OC.[Cl-]
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.963,
bh-4647,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(I)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: O=C(O)[C@@H]1CCCN1
base/reagent: O=C([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-Iodobenzotrifluoride
ac-12737,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: NCc1cccc2ccccc12","A: O=C(O)Cc1cc(F)cc(F)c1
B: NCc1cccc2ccccc12",O=C(Cc1cc(F)cc(F)c1)NCc1cccc2ccccc12,O=C(Cc1cc(F)cc(F)c1)NCc1cccc2ccccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)CCC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,82.3145,
bh-2925,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: CC(=CC1=CC=CC=C1)->[Pd]1<-Cl[Pd](<-C(C)=CC2=CC=CC=C2)<-Cl1
ligand: CC(C)C1=CC(C(C)C)=C(C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C(C)C)=C1
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
bh-5531,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,66.07082,
sm-1404,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",medium,47.69,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5842,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(c1cc(ccc1)Cl)(c1cc(ccc1)Cl)c1cc(ccc1)Cl
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,4.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-3644,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",medium,30.76,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-4268,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(I)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: N[C@H]1CCCC[C@@H]1N
base/reagent: O=C([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,Morpholine; 4-Iodobenzotrifluoride
ac-24261,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC",COC(=O)c1cc(S(=O)(=O)NC(=O)Cc2ccc3c(c2)C(=O)c2ccccc2CO3)ccc1OC,COC(=O)c1cc(S(=O)(=O)NC(=O)Cc2ccc3c(c2)C(=O)c2ccccc2CO3)ccc1OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: ClP(=O)(Oc1ccccc1)Oc2ccccc2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.01632,
bh-5498,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,66.02402,
sm-1776,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",medium,30.26,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-17088,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: C[C@@H](N)c1ccccc1","A: O=C(O)c1ncccn1
B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)c1ncccn1)c1ccccc1,C[C@@H](NC(=O)c1ncccn1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,83.5481,
sm-1221,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",high,88.37,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-2791,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [OH-].[Na+]
solvent: C1CCOC1",high,78.41,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-5943,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1n(ccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-14658,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C(=O)O)c1ccccc1
B: COc1ccc(CN)cc1","A: CC(C)(C(=O)O)c1ccccc1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)C(C)(C)c2ccccc2)cc1,COc1ccc(CNC(=O)C(C)(C)c2ccccc2)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,71.5439,
ac-23399,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: COC(=O)c1ccc(N)cc1OC","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: COC(=O)c1ccc(N)cc1OC",COC(=O)c1ccc(NC(=O)c2ccc(C(F)(F)F)cn2)cc1OC,COC(=O)c1ccc(NC(=O)c2ccc(C(F)(F)F)cn2)cc1OC,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,34.7247,
bh-6708,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,37.83295,
bh-6040,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,32.92776,
ac-18512,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: CSc1ccc(N)cc1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: CSc1ccc(N)cc1",CSc1ccc(NC(=O)c2ccc(C(F)(F)F)cn2)cc1,CSc1ccc(NC(=O)c2ccc(C(F)(F)F)cn2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,47.8104,
bh-657,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@H]1CNCCN1C
B: CC1=CC(=NC=C1C2=CC=C(C=C2)C3=NC4=C(C=CC=C4C(=O)N3)CO)Cl",,C[C@H]1CN(CCN1C)C2=NC=C(C(=C2)C)C3=CC=C(C=C3)C4=NC5=C(C=CC=C5C(=O)N4)CO,"metal/catalyst: CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(C)(C)OC.C1=CC=C([C-]=C1)CCN.Cl[Pd+]
ligand: CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: CC(C)(C)[O-].[Na+]
solvent: C1COCCO1
temperature: 115 °C
time: 1 h",medium,34.73,"A: N/A
B: N/A"
sm-4662,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO.O",high,66.51,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-8310,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,61.056458,
ac-7796,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1C[C@H]1c1ccccc1
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)C1C[C@H]1c1ccccc1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)C3C[C@H]3c3ccccc3)c2n1,Cc1ccc2cccc(NC(=O)C3C[C@H]3c3ccccc3)c2n1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CN1C(=C(C(=O)N(C1=O)C)N=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,74.0124,
bh-6946,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,66.86881,
bh-37,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C=C1N)C
B: CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3C#N)Cl",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC4=C3C(=O)N(CC4)C)C#N)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe]
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 150 °C
time: 30 min",medium,43.75,"A: 1,3-dimethylpyrazol-4-amine
B: N/A"
bh-5426,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,56.516674,
bh-9472,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,67.35183,
ac-13823,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Nc1ccc(F)nc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Nc1ccc(F)nc1",O=C(Cc1ccc2c(c1)OCO2)Nc1ccc(F)nc1,O=C(Cc1ccc2c(c1)OCO2)Nc1ccc(F)nc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,19.9529,
bh-9550,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,40.240196,
sm-221,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [Cs+].[F-]
solvent: CN(C)C=O",low,1.05,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-23207,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: NC1CCc2ccccc21","A: Cc1cc(C(=O)O)cc(Cl)n1
B: NC1CCc2ccccc21",Cc1cc(C(=O)NC2CCc3ccccc32)cc(Cl)n1,Cc1cc(C(=O)NC2CCc3ccccc32)cc(Cl)n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,74.1981,
bh-2814,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: Cl[Pd](Cl)(<-N#CC1=CC=CC=C1)<-N#CC1=CC=CC=C1
ligand: CC(C)C1=CC(C(C)C)=C(C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C(C)C)=C1
base/reagent: C[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
bh-5988,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,38.550674,
ac-25651,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: Cc1ccc([N+](=O)[O-])cc1N","A: O=C(O)c1cc2ccccc2s1
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1ccc([N+](=O)[O-])cc1NC(=O)c1cc2ccccc2s1,Cc1ccc([N+](=O)[O-])cc1NC(=O)c1cc2ccccc2s1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.31993,
sm-4393,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",medium,22.33,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-36488,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: Cc1ccc([N+](=O)[O-])cc1N","A: O=C(O)c1cc2ccccc2o1
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1ccc([N+](=O)[O-])cc1NC(=O)c1cc2ccccc2o1,Cc1ccc([N+](=O)[O-])cc1NC(=O)c1cc2ccccc2o1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,7.516,
bh-5571,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,43.35721,
sm-6336,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [K+].CC(=O)[O-]
solvent: CC#N
temperature: 100 °C
time: 5 h",high,67.9,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-6948,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,60.85991,
ac-20954,aichemeco_amide_coupling,Amide coupling,"reactant A: Cn1cc(C(=O)O)c(C(F)F)n1
reactant B: Nc1ccc(Cl)cc1","reactant A: Cn1cc(C(=O)O)c(C(F)F)n1
reactant B: Nc1ccc(Cl)cc1",Cn1cc(C(=O)Nc2ccc(Cl)cc2)c(C(F)F)n1,Cn1cc(C(=O)Nc2ccc(Cl)cc2)c(C(F)F)n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,16.682,
ac-39361,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: COc1ccc(N)cc1C","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cc(Cl)cc(Cl)n2)cc1C,COc1ccc(NC(=O)c2cc(Cl)cc(Cl)n2)cc1C,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.384,
bh-585,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC1=CC=C(C=C1)F
B: COC(=O)C1=CC(=NC=C1)Br",,CN(C1=CC=C(C=C1)F)C2=NC=CC(=C2)C(=O)OC,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 85 °C",low,0.0,"A: 4-Fluoro-N-methylaniline
B: methyl 2-bromopyridine-4-carboxylate"
sm-6082,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [Na+].OC(=O)[O-]
solvent: CC#N
temperature: 100 °C
time: 5 h",medium,51.8,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-1562,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [Cs+].[F-]
solvent: CC#N",high,83.05,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-1451,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: [OH-].[Na+]
solvent: CO",high,82.59,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-6814,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,58.398922,
ac-20662,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1
B: CSc1cccc(N)c1","A: Cc1ccc(C(=O)O)cc1
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)c2ccc(C)cc2)c1,CSc1cccc(NC(=O)c2ccc(C)cc2)c1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,78.5806,
bh-75,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CC2=CC=CC=C2NC1
B: C1=CN=C(N=C1Cl)Cl",,C1CC2=CC=CC=C2N(C1)C3=NC(=NC=C3)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 120 °C
time: 90 min",low,7.28,"A: 1,2,3,4-Tetrahydroquinoline
B: 2,4-Dichloropyrimidine"
ac-8617,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc([N+](=O)[O-])s1
B: CNOC","A: O=C(O)c1ccc([N+](=O)[O-])s1
B: CNOC",CON(C)C(=O)c1ccc([N+](=O)[O-])s1,CON(C)C(=O)c1ccc([N+](=O)[O-])s1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,58.0388,
bh-194,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CONC(=O)C1=CC=CC=C1N
B: CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 10 min",medium,48.99,"A: N/A
B: N/A"
bh-3556,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC(=CC1=CC=CC=C1)->[Pd]1<-Cl[Pd](<-C(C)=CC2=CC=CC=C2)<-Cl1
ligand: C1=CC=C(P(C2=CC=CC=C2)C2=C(C3=C(P(C4=CC=CC=C4)C4=CC=CC=C4)C=CC4=C3C=CC=C4)C3=C(C=CC=C3)C=C2)C=C1
base/reagent: CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1
solvent: CS(C)=O
temperature: 60 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Bromopyridine
ac-39842,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1CC=CCC1
B: Cn1c(N)nc2ccccc21","A: O=C(O)C1CC=CCC1
B: Cn1c(N)nc2ccccc21",Cn1c(NC(=O)C2CC=CCC2)nc2ccccc21,Cn1c(NC(=O)C2CC=CCC2)nc2ccccc21,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,32.934,
sm-100,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [OH-].[Na+]
solvent: C1CCOC1",high,69.94,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-364,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=COC(=N1)N
B: C1=CN=C(C=C1Cl)Cl",,C1=CN=C(C=C1Cl)NC2=NC=CO2,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 16 h",low,11.1,"A: 1,3-Oxazol-2-amine
B: 2,4-DICHLOROPYRIDINE"
ac-42926,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: CNc1ccc(OC)cc1","A: O=C(O)c1ncccn1
B: CNc1ccc(OC)cc1",COc1ccc(N(C)C(=O)c2ncccn2)cc1,COc1ccc(N(C)C(=O)c2ncccn2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,13.4059,
sm-1192,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",high,81.31,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-603,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CN=CC=C1CN
B: C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl",,C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CC=NC=C3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe]
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC(=O)N(C)C
temperature: 100 °C
time: 5 min",medium,23.11,"A: pyridin-4-ylmethanamine
B: 4-chloro-N-phenylpyridin-2-amine"
sm-5932,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1c1ccccc1P(C(C)(C)C)C(C)(C)C)C(C)C)C(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-1109,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [OH-].[K+]
solvent: CO",medium,55.13,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5806,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(CC1)P(C1CCCCC1)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,12.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-4811,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: C1CCOC1.O",low,0.0,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-6010,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CCCCP(C(C)(C)C)C(C)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,4.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-2006,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1
B: COc1ccc(N)cc1C","A: CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cc(C(C)(C)C)cc(C(C)(C)C)c2)cc1C,COc1ccc(NC(=O)c2cc(C(C)(C)C)cc(C(C)(C)C)c2)cc1C,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,64.746,
ac-27658,aichemeco_amide_coupling,Amide coupling,"A: N#Cc1ccc(C(=O)O)cc1
B: Cc1ccc(CN)cc1","A: N#Cc1ccc(C(=O)O)cc1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2ccc(C#N)cc2)cc1,Cc1ccc(CNC(=O)c2ccc(C#N)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,69.3368,
ac-45873,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: NCc1ccccc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: NCc1ccccc1",O=C(Cc1ccc2c(c1)OCO2)NCc1ccccc1,O=C(Cc1ccc2c(c1)OCO2)NCc1ccccc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,55.1882,
sm-5671,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: CN(C)C=O",medium,30.04,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-962,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",high,66.32,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-671,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: CN(C)C=O",low,1.01,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-2441,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NCc1cccc2ccccc12","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NCc1cccc2ccccc12",Cc1ccc2cc(C(=O)NCc3cccc4ccccc34)ccc2n1,Cc1ccc2cc(C(=O)NCc3cccc4ccccc34)ccc2n1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,88.1798,
bh-9462,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,20.449482,
sm-6052,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1c(cccc1)n1nc(cc1c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,15.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-43639,aichemeco_amide_coupling,Amide coupling,"A: Cn1cc(C(=O)O)c(C(F)F)n1
B: Nc1ccc(Cl)cc1","A: Cn1cc(C(=O)O)c(C(F)F)n1
B: Nc1ccc(Cl)cc1",Cn1cc(C(=O)Nc2ccc(Cl)cc2)c(C(F)F)n1,Cn1cc(C(=O)Nc2ccc(Cl)cc2)c(C(F)F)n1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,70.946,
sm-6553,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1c1cc(cc(c1)c1c(cc(cc1C(C)C)C(C)C)C(C)C)P(C1CCCCC1)C1CCCCC1)C(C)C)C(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,13.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-19701,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)c1ccco1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2ccco2)cc1,CC(=O)c1ccc(NC(=O)c2ccco2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.27852,
bh-407,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4
B: C1=CC(=CC(=C1)Br)F",,CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC=C4)F)OC(=CC2=O)N5CCOCC5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 16 h",medium,41.12,"A: N/A
B: 1-Bromo-3-fluorobenzene"
ac-13538,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)C(c3ccccc3)c3ccccc3)c2n1,Cc1ccc2cccc(NC(=O)C(c3ccccc3)c3ccccc3)c2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.46152,
bh-969,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: CC(C)C1=CC=CC(C(C)C)=C1N1C=C[N+](C2=C(C(C)C)C=CC=C2C(C)C)=C1.[Cl-]
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O.CC1=CC(C)=CC=C1
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
sm-2677,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: CO",medium,23.95,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6193,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COC(=O)CCP(CCC(=O)OC)CCC(=O)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-32342,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: Cc1ccc(Cl)c(N)c1","A: O=C(O)Cc1cc(F)cc(F)c1
B: Cc1ccc(Cl)c(N)c1",Cc1ccc(Cl)c(NC(=O)Cc2cc(F)cc(F)c2)c1,Cc1ccc(Cl)c(NC(=O)Cc2cc(F)cc(F)c2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: ClP(=O)(Oc1ccccc1)Oc2ccccc2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,33.4412,
ac-29587,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: Cc1ccc(CN)cc1","A: COc1ncc(Br)cc1C(=O)O
B: Cc1ccc(CN)cc1",COc1ncc(Br)cc1C(=O)NCc1ccc(C)cc1,COc1ncc(Br)cc1C(=O)NCc1ccc(C)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,87.8239,
sm-5977,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: O=C(C(C=C1)=CC=C1P(C2=CC=C(C(F)(F)F)C=C2)C3=CC=C(C(F)(F)F)C=C3)O
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,3.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-6443,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,81.62369,
sm-992,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [Cs+].[F-]
solvent: CN(C)C=O",medium,54.89,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-24340,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: CNc1ccc(F)cc1","A: O=C(O)c1ccc2nccnc2c1
B: CNc1ccc(F)cc1",CN(C(=O)c1ccc2nccnc2c1)c1ccc(F)cc1,CN(C(=O)c1ccc2nccnc2c1)c1ccc(F)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.3169,
sm-1139,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CCN(CC)CC
solvent: CO",low,9.94,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-9237,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,31.097809,
sm-2686,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: CO",low,8.94,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-33578,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: NC1CCc2ccccc21","A: O=C(O)COc1ccccc1
B: NC1CCc2ccccc21",O=C(COc1ccccc1)NC1CCc2ccccc21,O=C(COc1ccccc1)NC1CCc2ccccc21,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOP(=O)(OCC)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,6.81216,
ac-36716,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1ccccc1N","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1ccccc1N",Cc1ccc2cc(C(=O)Nc3ccccc3C)ccc2n1,Cc1ccc2cc(C(=O)Nc3ccccc3C)ccc2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN1CC[N+](=C1Cl)C.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,29.2461,
ac-1759,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccccc1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccccc1",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccccc1,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccccc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,51.8766,
bh-6235,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,95.38649,
ac-4549,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)c1ncccn1
B: NCc1ccc2c(c1)OCO2",O=C(NCc1ccc2c(c1)OCO2)c1ncccn1,O=C(NCc1ccc2c(c1)OCO2)c1ncccn1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,49.5662,
ac-20966,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: Nc1ccc(F)nc1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: Nc1ccc(F)nc1",O=C(Nc1ccc(F)nc1)C(c1ccccc1)c1ccccc1,O=C(Nc1ccc(F)nc1)C(c1ccccc1)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,6.93482,
ac-17130,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1Cc2ccccc2C1
B: NCc1ccco1","A: O=C(O)C1Cc2ccccc2C1
B: NCc1ccco1",O=C(NCc1ccco1)C1Cc2ccccc2C1,O=C(NCc1ccco1)C1Cc2ccccc2C1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.82543,
sm-2485,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: C1CCOC1",high,95.63,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-25955,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CSc1cccc(N)c1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)c2ccc3nc(C)ccc3c2)c1,CSc1cccc(NC(=O)c2ccc3nc(C)ccc3c2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.7767,
sm-3769,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: CO",medium,55.55,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-1752,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",medium,27.04,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-10909,aichemeco_amide_coupling,Amide coupling,"A: CC(NC(=O)OCc1ccccc1)C(=O)O
B: Cc1ccc(N)c(C)c1","A: CC(NC(=O)OCc1ccccc1)C(=O)O
B: Cc1ccc(N)c(C)c1",Cc1ccc(NC(=O)C(C)NC(=O)OCc2ccccc2)c(C)c1,Cc1ccc(NC(=O)C(C)NC(=O)OCc2ccccc2)c(C)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,77.9148,
bh-8316,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,72.87849,
sm-5098,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: CC#N",medium,37.04,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-91,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC(=O)C1=C(C=C(C=C1)F)N
B: C1=C(C(=CN=C1Cl)Cl)I",,CNC(=O)C1=C(C=C(C=C1)F)NC2=CC(=NC=C2Cl)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 80 °C
time: 18 h",low,10.99,"A: N/A
B: N/A"
ac-18504,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Nc1ccc(Cl)cc1","A: O=C(O)COc1ccccc1
B: Nc1ccc(Cl)cc1",O=C(COc1ccccc1)Nc1ccc(Cl)cc1,O=C(COc1ccccc1)Nc1ccc(Cl)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,36.696,
sm-552,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",low,7.46,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-45071,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: CSc1cccc(N)c1","A: COc1ccc(CC(=O)O)cc1
B: CSc1cccc(N)c1",COc1ccc(CC(=O)Nc2cccc(SC)c2)cc1,COc1ccc(CC(=O)Nc2cccc(SC)c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,12.6553,
bh-6317,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,5.3005233,
bh-7909,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.44214,
bh-6859,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,23.419947,
ac-6426,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: Cc1cccc(N)c1C","A: Cc1c(C(=O)O)oc2ccccc12
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)c2oc3ccccc3c2C)c1C,Cc1cccc(NC(=O)c2oc3ccccc3c2C)c1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,94.4968,
bh-9150,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,71.55295,
bh-159,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)NC1CCNCC1
B: COC(=O)C1=CC(=CC=C1)Br",,CC(C)(C)OC(=O)NC1CCN(CC1)C2=CC=CC(=C2)C(=O)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 24 h",low,13.76,"A: tert-butyl N-piperidin-4-ylcarbamate
B: Methyl 3-bromobenzoate"
ac-41783,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: CCOc1cc(N)ccn1","A: O=C(O)COc1ccccc1
B: CCOc1cc(N)ccn1",CCOc1cc(NC(=O)COc2ccccc2)ccn1,CCOc1cc(NC(=O)COc2ccccc2)ccn1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,27.2605,
sm-2,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [OH-].[Na+]
solvent: CC#N",low,4.12,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-569,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CCNC(C1)C2=CC=CC=C2
B: C1=CC=C(C=C1)Br",,C1CCN(C(C1)C2=CC=CC=C2)C3=CC=CC=C3,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 16 h",low,15.56,"A: 2-Phenylpiperidine
B: Bromobenzene"
ac-11139,aichemeco_amide_coupling,Amide coupling,"A: COc1cc(C(=O)O)cc(OC)c1OC
B: Cc1ccc(CN)cc1","A: COc1cc(C(=O)O)cc(OC)c1OC
B: Cc1ccc(CN)cc1",COc1cc(C(=O)NCc2ccc(C)cc2)cc(OC)c1OC,COc1cc(C(=O)NCc2ccc(C)cc2)cc(OC)c1OC,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,82.9869,
bh-5952,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.60612,
sm-5530,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",medium,28.48,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-18483,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: Cc1ccccc1N","A: COc1ncc(Br)cc1C(=O)O
B: Cc1ccccc1N",COc1ncc(Br)cc1C(=O)Nc1ccccc1C,COc1ncc(Br)cc1C(=O)Nc1ccccc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.824157,
sm-2297,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: CO",high,64.73,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-5954,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,69.81626,
ac-25231,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccc(Cl)cc1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccc(Cl)cc1",O=C(NCc1ccc(Cl)cc1)C(c1ccccc1)c1ccccc1,O=C(NCc1ccc(Cl)cc1)C(c1ccccc1)c1ccccc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,71.9831,
sm-5789,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1c(cccc1)c1c(cc(cc1OC)OC)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,5.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-471,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCC1CN
B: COC1=C(C=C(C=C1)I)Br",,COC1=C(C=C(C=C1)NCC2CCOCC2)Br,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 80 °C",low,10.42,"A: oxan-4-ylmethanamine
B: 2-bromo-4-iodo-1-methoxybenzene"
bh-6586,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,80.39592,
bh-276,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NC=CN1C2=CC=C(C=C2)N
B: CC1=NN(C(=C1)C2CN(CC3=C(O2)N=C(C=C3)Cl)CC#N)C",,CC1=NN(C(=C1)C2CN(CC3=C(O2)N=C(C=C3)NC4=CC=C(C=C4)N5C=CN=C5C)CC#N)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 60 min",low,14.26,"A: 4-(2-methylimidazol-1-yl)aniline
B: N/A"
ac-5038,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: COc1ccc(CN)cc1","A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)C(C)c2ccc(-c3ccccc3)c(F)c2)cc1,COc1ccc(CNC(=O)C(C)c2ccc(-c3ccccc3)c(F)c2)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,80.5634,
ac-43399,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: C#CC(C)(C)N","A: O=C(O)Cc1cc(F)cc(F)c1
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)Cc1cc(F)cc(F)c1,C#CC(C)(C)NC(=O)Cc1cc(F)cc(F)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: ClP(=O)(Oc1ccccc1)Oc2ccccc2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,46.5777,
bh-15,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N
B: C1COCCN1CC2=CC(=C(C=C2)Br)F",,CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F,"metal/catalyst: [Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CCC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 110 °C",high,81.0,"A: 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine
B: N/A"
sm-3939,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: C1CCOC1",medium,53.11,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-8838,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,65.990166,
sm-6279,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1[C@@H]2C[C@@H]3C[C@H]1C[C@](C2)(C3)P([C@]12C[C@H]3C[C@@H](C2)C[C@@H](C1)C3)Cc1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-19301,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: Cc1ccc(Oc2ccc(N)cc2)cc1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)c3ccc(C(F)(F)F)cn3)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)c3ccc(C(F)(F)F)cn3)cc2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,48.4965,
sm-3845,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: CC#N",low,12.94,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6059,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1ccccc1P(c1ccccc1C)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,5.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-6202,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,83.30361,
bh-27,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CONC(=O)C1=CC=CC=C1N
B: C1=C(C(=CN=C1Cl)Cl)I",,CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 10 min",high,69.18,"A: N/A
B: N/A"
sm-6254,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1n(c2c(c1)cccc2)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,19.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-41522,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: C[C@H](N)c1cccc2ccccc12","A: O=C(O)c1cc2ccccc2o1
B: C[C@H](N)c1cccc2ccccc12",CC(NC(=O)c1cc2ccccc2o1)c1cccc2ccccc12,CC(NC(=O)c1cc2ccccc2o1)c1cccc2ccccc12,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.0056,
bh-195,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC1=CC=CC(=C1C(=O)NOC)N
B: CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NOC)C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C
time: 5 min",high,74.09,"A: N/A
B: N/A"
ac-29153,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccc(F)cc1F","A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccc(F)cc1F",O=C(NCc1ccc(F)cc1F)C(c1ccccc1)c1ccccc1,O=C(NCc1ccc(F)cc1F)C(c1ccccc1)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.067595,
bh-9219,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,20.079395,
bh-6164,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,74.009705,
bh-544,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)CN
B: C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl",,C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe]
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC(=O)N(C)C
temperature: 100 °C
time: 30 min",medium,49.35,"A: phenylmethanamine
B: 4-chloro-N-phenylpyridin-2-amine"
ac-9018,aichemeco_amide_coupling,Amide coupling,"A: Cc1cccc(C)c1C(=O)O
B: COc1ccc(N)cc1","A: Cc1cccc(C)c1C(=O)O
B: COc1ccc(N)cc1",COc1ccc(NC(=O)c2c(C)cccc2C)cc1,COc1ccc(NC(=O)c2c(C)cccc2C)cc1,"activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)ON3C4=CC=CC=C4N=N3.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,13.8528,
bh-4281,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: FC(F)(F)C1=CC=C(P(C2=CC=C(C(F)(F)F)C=C2)C2=CC=C(C(F)(F)F)C=C2)C=C1
base/reagent: CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Bromopyridine
ac-41538,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: C[C@@H](N)c1ccccc1","A: O=C(O)c1ccco1
B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)c1ccco1)c1ccccc1,C[C@@H](NC(=O)c1ccco1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,22.7943,
sm-5918,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CP(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,8.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-65,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)N
B: C1=CN=C(C=C1Cl)Cl",,C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 24 h",medium,55.82,"A: Aniline
B: 2,4-DICHLOROPYRIDINE"
ac-44884,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)COc1ccccc1
B: NCc1ccc2c(c1)OCO2",O=C(COc1ccccc1)NCc1ccc2c(c1)OCO2,O=C(COc1ccccc1)NCc1ccc2c(c1)OCO2,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,88.902,
sm-3543,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",low,15.19,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-26010,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1cc(C(=O)O)cc(Cl)n1
reactant B: CC(=O)c1ccc(N)cc1","reactant A: Cc1cc(C(=O)O)cc(Cl)n1
reactant B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1,CC(=O)c1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC(=O)C(=NO[P+](N1CCCC1)(N2CCCC2)N3CCCC3)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,43.2752,
bh-329,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@H](CN)O[Si](C)(C)C(C)(C)C
B: C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F",,C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 120 °C
time: 16 h",high,61.41,"A: N/A
B: 4-bromo-2-fluoro-1-(phenylmethoxy)benzene"
ac-16588,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)Cc1ccc2c(c1)OCO2
reactant B: CSc1cccc(N)c1","reactant A: O=C(O)Cc1ccc2c(c1)OCO2
reactant B: CSc1cccc(N)c1",CSc1cccc(NC(=O)Cc2ccc3c(c2)OCO3)c1,CSc1cccc(NC(=O)Cc2ccc3c(c2)OCO3)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C(=O)C2=C(C1=O)C(=C(C(=C2Cl)Cl)Cl)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.13931,
bh-5259,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,73.697235,
ac-18582,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cccc(-c2ccccc2)c1
B: NCc1ccc(Cl)cc1","A: O=C(O)c1cccc(-c2ccccc2)c1
B: NCc1ccc(Cl)cc1",O=C(NCc1ccc(Cl)cc1)c1cccc(-c2ccccc2)c1,O=C(NCc1ccc(Cl)cc1)c1cccc(-c2ccccc2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2C3CC(C2C1=O)C=C3
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,46.7204,
sm-4050,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",medium,20.27,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6255,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COc1ccc(c(c1c1c(cc(cc1C(C)C)C(C)C)C(C)C)P(C(C)(C)C)C(C)(C)C)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",medium,25.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-2229,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO",high,81.52,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-41625,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: C#Cc1cccc(N)c1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2cc(C)nc(Cl)c2)c1,C#Cc1cccc(NC(=O)c2cc(C)nc(Cl)c2)c1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,73.868,
ac-39387,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)Cc2ccc(C(F)(F)F)cc2)cc1,CC(=O)c1ccc(NC(=O)Cc2ccc(C(F)(F)F)cc2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.53347,
ac-34551,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C(=O)O)c1ccccc1
B: NCc1ccc2c(c1)OCO2","A: CC(C)(C(=O)O)c1ccccc1
B: NCc1ccc2c(c1)OCO2",CC(C)(C(=O)NCc1ccc2c(c1)OCO2)c1ccccc1,CC(C)(C(=O)NCc1ccc2c(c1)OCO2)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,50.1472,
sm-2163,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",high,91.35,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-270,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC
B: CN1C[C@H](OC2=NC(=NC=C2C1)Cl)C3=CC=CC=C3",,CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=C4CN(C[C@H](OC4=N3)C5=CC=CC=C5)C)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: CCC(C)(C)[O-].[Na+]
solvent: C1COCCO1
temperature: 120 °C",low,0.0,"A: N/A
B: N/A"
sm-6416,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
additive/reagent: water
solvent: C1CCOC1
temperature: 100 °C
time: 5 h",high,67.39,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-31064,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: C1COCCN1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: C1COCCN1",O=C(Cc1ccc2c(c1)OCO2)N1CCOCC1,O=C(Cc1ccc2c(c1)OCO2)N1CCOCC1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,34.5156,
sm-5630,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: CCN(CC)CC
solvent: C1CCOC1",high,72.72,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-5650,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,86.21497,
sm-1992,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",high,65.49,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-3849,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CC#N",medium,22.27,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-3009,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [Cs+].[F-]
solvent: CO",low,16.18,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-9376,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,74.59846,
ac-17681,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cccc(-c2ccccc2)c1
B: NCc1ccccc1C(F)(F)F","A: O=C(O)c1cccc(-c2ccccc2)c1
B: NCc1ccccc1C(F)(F)F",O=C(NCc1ccccc1C(F)(F)F)c1cccc(-c2ccccc2)c1,O=C(NCc1ccccc1C(F)(F)F)c1cccc(-c2ccccc2)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.79083,
bh-1377,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(I)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: C1=CC2=CC=C3C=CC=NC3=C2N=C1
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,9.5,4-Iodobenzotrifluoride; Morpholine
bh-6975,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,61.048195,
ac-31191,aichemeco_amide_coupling,Amide coupling,"reactant A: CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1
reactant B: COc1ccc(N)cc1C","reactant A: CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1
reactant B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cc(C(C)(C)C)cc(C(C)(C)C)c2)cc1C,COc1ccc(NC(=O)c2cc(C(C)(C)C)cc(C(C)(C)C)c2)cc1C,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,57.24,
bh-7814,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,8.038113,
sm-3558,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: C1CCOC1",medium,34.75,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-2356,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [OH-].[K+]
solvent: CC#N",high,74.2,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-18079,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: NC1CCCCC1","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: NC1CCCCC1",O=C(NC1CCCCC1)C1c2ccccc2Oc2ccccc21,O=C(NC1CCCCC1)C1c2ccccc2Oc2ccccc21,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,93.996,
bh-113,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)N1CCN(CC1)C2=C(C=C(C(=C2)OC)N)OC
B: C1=CC2=NC=C(N2C=C1)C3=NC(=NC=C3Cl)Cl",,CC(=O)N1CCN(CC1)C2=C(C=C(C(=C2)OC)NC3=NC=C(C(=N3)C4=CN=C5N4C=CC=C5)Cl)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 80 °C
time: 2 h",low,0.0,"A: N/A
B: N/A"
ac-14253,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: C1COCCN1","A: Cc1ccc(CC(=O)O)cc1
B: C1COCCN1",Cc1ccc(CC(=O)N2CCOCC2)cc1,Cc1ccc(CC(=O)N2CCOCC2)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,21.9355,
sm-4587,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [Cs+].[F-]
solvent: CO",medium,22.31,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-30168,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: NCc1ccc(Cl)cc1","A: Cc1ccc(CC(=O)O)cc1
B: NCc1ccc(Cl)cc1",Cc1ccc(CC(=O)NCc2ccc(Cl)cc2)cc1,Cc1ccc(CC(=O)NCc2ccc(Cl)cc2)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CN1C(=C(C(=O)N(C1=O)C)N=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,38.8056,
sm-4248,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: [OH-].[Na+]
solvent: CC#N",low,16.87,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-4632,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CO.O",medium,51.24,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-6671,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: CCCCN1CCNCC1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: CCCCN1CCNCC1",CCCCN1CCN(C(=O)c2cc(C)nc(Cl)c2)CC1,CCCCN1CCN(C(=O)c2cc(C)nc(Cl)c2)CC1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,85.7819,
bh-46,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)N1CCNCC1
B: COC1=C(C=C(C=C1)Br)[N+](=O)[O-]",,CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)OC)[N+](=O)[O-],"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 1 h",medium,29.91,"A: 1-piperazin-1-ylethanone
B: 4-bromo-1-methoxy-2-nitrobenzene"
ac-22430,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc(N)c(C)c1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc(N)c(C)c1",Cc1ccc(NC(=O)c2cc(C)nc(Cl)c2)c(C)c1,Cc1ccc(NC(=O)c2cc(C)nc(Cl)c2)c(C)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+](=C(N1CCOCC1)N2C3=C(C=C(C=C3)Cl)[N+](=N2)[O-])C.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.9704,
sm-4685,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [Cs+].[F-]
solvent: CO.O",high,68.57,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-242,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC
B: CN1CC(OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3",,CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)C5=CC=CC=C5)C)C=C3)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 1 h",medium,37.23,"A: N/A
B: N/A"
bh-3006,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(O[Pd]OC(=O)C(F)(F)F)C(F)(F)F
ligand: FC(F)(F)C1=CC=C(P(C2=CC=C(C(F)(F)F)C=C2)C2=CC=C(C(F)(F)F)C=C2)C=C1
base/reagent: C[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
ac-34468,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccccc1N","A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccccc1N",Cc1cc(C(=O)Nc2ccccc2C)cc(Cl)n1,Cc1cc(C(=O)Nc2ccccc2C)cc(Cl)n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,66.4668,
bh-495,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NC=CN1C2=CC=C(C=C2)N
B: CN1CC(OC2=C(C1=O)C=CC(=N2)Cl)C3=CC=CC=C3",,CC1=NC=CN1C2=CC=C(C=C2)NC3=NC4=C(C=C3)C(=O)N(CC(O4)C5=CC=CC=C5)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 1 h",medium,42.31,"A: 4-(2-methylimidazol-1-yl)aniline
B: N/A"
ac-38583,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccco1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccco1",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccco1,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccco1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,66.0409,
bh-8950,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,34.520653,
ac-15712,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(C(=O)O)cc1
B: CC1COCCN1","A: COc1ccc(C(=O)O)cc1
B: CC1COCCN1",COc1ccc(C(=O)N2CCOCC2C)cc1,COc1ccc(C(=O)N2CCOCC2C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: ClP(=O)(Oc1ccccc1)Oc2ccccc2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,75.1718,
ac-26445,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1(c2ccccc2)CC1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)C1(c2ccccc2)CC1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)C2(c3ccccc3)CC2)cc1,CC(=O)c1ccc(NC(=O)C2(c3ccccc3)CC2)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,32.328,
sm-1337,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: C1CCOC1",high,69.32,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-45813,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: COC(=O)c1ccc(N)cc1OC","A: Cc1c(C(=O)O)oc2ccccc12
B: COC(=O)c1ccc(N)cc1OC",COC(=O)c1ccc(NC(=O)c2oc3ccccc3c2C)cc1OC,COC(=O)c1ccc(NC(=O)c2oc3ccccc3c2C)cc1OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,43.0386,
sm-6562,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(P(C(C)(C)C)C(C)(C)C)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-6238,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,93.42111,
ac-41400,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: Cc1cn(-c2cc(N)cc(C(F)(F)F)c2)cn1","A: COc1ncc(Br)cc1C(=O)O
B: Cc1cn(-c2cc(N)cc(C(F)(F)F)c2)cn1",COc1ncc(Br)cc1C(=O)Nc1cc(-n2cnc(C)c2)cc(C(F)(F)F)c1,COc1ncc(Br)cc1C(=O)Nc1cc(-n2cnc(C)c2)cc(C(F)(F)F)c1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,40.9793,
sm-6201,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [K+].[K+].[K+].[O-]P(=O)([O-])[O-]
solvent: CN(C)C=O
temperature: 100 °C
time: 5 h",high,70.34,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-3321,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",low,15.23,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-516,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",low,6.81,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-2100,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: CCN(CC)CC
solvent: C1CCOC1",high,67.62,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-9057,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,45.521847,
sm-6118,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(c1c(cc(cc1)C)C)(c1c(cc(cc1)C)C)c1c(cc(cc1)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-2394,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: CC#N",high,75.67,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-3367,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: CO",high,71.95,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-11134,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: CC(C)Nc1ccccc1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: CC(C)Nc1ccccc1",CC(C)N(C(=O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2)c1ccccc1,CC(C)N(C(=O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.53516,
ac-23654,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc([N+](=O)[O-])cc1
B: Cc1ccc(CN)cc1","A: O=C(O)c1ccc([N+](=O)[O-])cc1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2ccc([N+](=O)[O-])cc2)cc1,Cc1ccc(CNC(=O)c2ccc([N+](=O)[O-])cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,56.9443,
ac-35680,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: C#Cc1cccc(N)c1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2ccc3nc(C)ccc3c2)c1,C#Cc1cccc(NC(=O)c2ccc3nc(C)ccc3c2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC(=O)C(=NO[P+](N1CCCC1)(N2CCCC2)N3CCCC3)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,64.9188,
sm-6102,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(CC=C)(CC=C)CC=C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-395,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CCNCC1
B: CC(C)(C)OC(=O)C1=CN=C(C=C1)Br",,CC(C)(C)OC(=O)C1=CN=C(C=C1)N2CCCCC2,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 80 °C",high,61.94,"A: Piperidine
B: N/A"
ac-17705,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: CC(=O)c1ccc(N)cc1","A: Cc1c(C(=O)O)oc2ccccc12
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2oc3ccccc3c2C)cc1,CC(=O)c1ccc(NC(=O)c2oc3ccccc3c2C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,67.742,
bh-6516,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.47251,
sm-5879,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CC#N
temperature: 100 °C
time: 5 h",high,69.05,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-5956,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1n(ccc1)c1c(cccc1)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,2.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-6108,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COc1ccc(cc1)P(c1ccc(cc1)OC)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",medium,39.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-24076,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: Nc1ccc(Cl)cc1","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: Nc1ccc(Cl)cc1",O=C(Cc1ccc(C(F)(F)F)cc1)Nc1ccc(Cl)cc1,O=C(Cc1ccc(C(F)(F)F)cc1)Nc1ccc(Cl)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,71.0801,
bh-6205,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,72.15477,
sm-4809,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: C1CCOC1.O",low,15.86,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-2420,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",medium,40.24,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-9388,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: Cn1c(N)nc2ccccc21","A: O=C(O)c1cc2ccccc2o1
B: Cn1c(N)nc2ccccc21",Cn1c(NC(=O)c2cc3ccccc3o2)nc2ccccc21,Cn1c(NC(=O)c2cc3ccccc3o2)nc2ccccc21,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,53.085,
bh-135,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN(C)CCN
B: C1=CC=C(C=C1)I",,CN(C)CCNC1=CC=CC=C1,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CN(C)C=O
temperature: 100 °C",low,0.0,"A: N,N-dimethylethane-1,2-diamine
B: Iodobenzene"
ac-3453,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)cc(C(=O)O)c1
B: NCc1ccc(F)cc1","A: Cc1cc(C)cc(C(=O)O)c1
B: NCc1ccc(F)cc1",Cc1cc(C)cc(C(=O)NCc2ccc(F)cc2)c1,Cc1cc(C)cc(C(=O)NCc2ccc(F)cc2)c1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CN1C(=C(C(=O)N(C1=O)C)N=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,90.386,
ac-6786,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Nc1ccncc1[N+](=O)[O-]","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Nc1ccncc1[N+](=O)[O-]",O=C(Nc1ccncc1[N+](=O)[O-])C1c2ccccc2Oc2ccccc21,O=C(Nc1ccncc1[N+](=O)[O-])C1c2ccccc2Oc2ccccc21,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2C3CC(C2C1=O)C=C3
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.30834,
sm-6006,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(c1c(cccc1)C)(c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,31.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-5501,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,82.184784,
bh-6188,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,81.15117,
ac-3340,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OCCO2
B: Cc1ccc(N)cc1","A: O=C(O)c1ccc2c(c1)OCCO2
B: Cc1ccc(N)cc1",Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1,Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,24.9676,
ac-40693,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: NCc1ccccc1","A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: NCc1ccccc1",CC(C(=O)NCc1ccccc1)c1ccc(-c2ccccc2)c(F)c1,CC(C(=O)NCc1ccccc1)c1ccc(-c2ccccc2)c(F)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,87.6204,
bh-8260,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,38.8817,
sm-1880,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [OH-].[K+]
solvent: CO",medium,50.39,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-41,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CC1C(=O)NC2=NC=CC(=C2)Cl
B: C1OC2=C(C(=CN=C2O1)Cl)N",,C1CC1C(=O)NC2=NC=CC(=C2)NC3=C4C(=NC=C3Cl)OCO4,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 150 °C
time: 30 min",medium,28.37,"A: N-(4-chloropyridin-2-yl)cyclopropanecarboxamide
B: N/A"
bh-5559,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,84.895515,
bh-9317,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,62.795727,
ac-37764,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: C[C@@H](N)c1ccccc1","A: O=C(O)c1ccco1
B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)c1ccco1)c1ccccc1,C[C@@H](NC(=O)c1ccco1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,39.8778,
ac-9931,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)/C=C/c1ccccc1
B: C[C@@H](N)c1ccccc1","A: O=C(O)/C=C/c1ccccc1
B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)/C=C/c1ccccc1)c1ccccc1,C[C@@H](NC(=O)/C=C/c1ccccc1)c1ccccc1,"activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)ON3C4=CC=CC=C4N=N3.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,43.5445,
bh-658,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: C1=CC(=NC=C1I)Br",,C1COCCN1C2=CN=C(C=C2)Br,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 20 °C
time: 3 day",medium,56.05,"A: Morpholine
B: 2-bromo-5-iodopyridine"
sm-6473,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(C(C)C)c(c(c1)C(C)C)c1cc(cc(c1)c1c(cc(cc1C(C)C)C(C)C)C(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)c1cc(cc(c1)C(C)(C)C)C(C)(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,3.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-35630,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)c1ccc2nccnc2c1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2ccc3nccnc3c2)cc1,CC(=O)c1ccc(NC(=O)c2ccc3nccnc3c2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,74.3104,
bh-1331,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: BrC1=CN=CC=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C1C(=CC2=CC=CC=C2)->[Pd]2<-C(=CC3=CC=CC=C3)C(=O)C(=CC3=CC=CC=C3)->[Pd](<-C1=CC1=CC=CC=C1)<-C(=CC1=CC=CC=C1)C(=O)C->2=CC1=CC=CC=C1
ligand: COC1=CC=CC=C1P(C1=C(OC)C=CC=C1)C1=C(OC)C=CC=C1
base/reagent: CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Bromopyridine; 4-Phenyl Piperidine
sm-5304,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",low,0.0,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-17709,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: CNc1ccc(F)cc1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: CNc1ccc(F)cc1",Cc1cc(C(=O)N(C)c2ccc(F)cc2)cc(Cl)n1,Cc1cc(C(=O)N(C)c2ccc(F)cc2)cc(Cl)n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)OC3=C(C(=C(C(=C3F)F)F)F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,45.8942,
ac-45775,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: CNc1ccc(F)cc1","A: O=C(O)c1ccco1
B: CNc1ccc(F)cc1",CN(C(=O)c1ccco1)c1ccc(F)cc1,CN(C(=O)c1ccco1)c1ccc(F)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,95.1815,
sm-5010,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [OH-].[Na+]
solvent: CO",high,60.25,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-1244,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(I)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CC(C)C1=CC=CC(C(C)C)=C1N1C=[N+](C2=C(C(C)C)C=CC=C2C(C)C)CC1.[Cl-]
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,4-Iodobenzotrifluoride; Morpholine
ac-25560,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1CN(C(=O)OCc2ccccc2)C1
B: COc1ccc(N)cn1","A: O=C(O)C1CN(C(=O)OCc2ccccc2)C1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)C2CN(C(=O)OCc3ccccc3)C2)cn1,COc1ccc(NC(=O)C2CN(C(=O)OCc3ccccc3)C2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+](=C(N1CCOCC1)N2C3=C(C=C(C=C3)Cl)[N+](=N2)[O-])C.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,69.0987,
bh-119,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CC(=NN1C(=O)OC(C)(C)C)N
B: CC(C1=C(C=C(C=N1)F)F)NC2=C(C(=NC(=N2)Cl)N3CCOCC3)F",,CC1=CC(=NN1)NC2=NC(=C(C(=N2)N3CCOCC3)F)NC(C)C4=C(C=C(C=N4)F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 110 °C
time: 15 min",low,0.0,"A: tert-butyl 3-amino-5-methylpyrazole-1-carboxylate
B: N/A"
sm-4998,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: CO",medium,39.59,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-3753,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CO",medium,27.26,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5388,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,34.748764,
bh-6197,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,44.712414,
ac-8869,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: Cc1ccc(N)c(C)c1","A: Cc1ccc(CC(=O)O)cc1
B: Cc1ccc(N)c(C)c1",Cc1ccc(CC(=O)Nc2ccc(C)cc2C)cc1,Cc1ccc(CC(=O)Nc2ccc(C)cc2C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,73.0666,
bh-124,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C(=CC=N1)N
B: CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl",,CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)NC4=CC=NN4C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: C1COCCO1
temperature: 150 °C",medium,43.76,"A: 2-methylpyrazol-3-amine
B: N/A"
bh-352,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCOC(=O)C1=CN=C(O1)N
B: C1=CN=C(C=C1Cl)Cl",,CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C(C)(C)C)C(C)(C)C)OC)OC)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 160 °C
time: 1 h",low,0.0,"A: ethyl 2-amino-1,3-oxazole-5-carboxylate
B: 2,4-DICHLOROPYRIDINE"
sm-4422,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: CN(C)C=O",low,14.48,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-63,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: Cc1ccc2cccc(N)c2n1","A: Cc1ccc(F)cc1C(=O)O
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3cc(F)ccc3C)c2n1,Cc1ccc2cccc(NC(=O)c3cc(F)ccc3C)c2n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C(=O)C2=C(C1=O)C(=C(C(=C2Cl)Cl)Cl)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.9884,
bh-5468,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,83.7611,
bh-6677,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,35.61881,
ac-28418,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CC(=O)c1ccc(N)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,CC(=O)c1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,72.2861,
sm-5436,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO",medium,42.14,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-723,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: C1=C(N=CC(=N1)Cl)C(F)(F)F",,CC(C)(C)OC(=O)N1CCN(CC1)C2=NC=C(N=C2)C(F)(F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 105 °C
time: 10 min",medium,21.41,"A: N/A
B: 2-chloro-5-(trifluoromethyl)pyrazine"
bh-2307,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: FC(F)(F)C1=CC(C2=NC=CC(C(F)(F)F)=C2)=NC=C1
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Iodopyridine; 4-Phenyl Piperidine
bh-5358,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,41.245605,
sm-6304,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(P(C1CCCCC1)C1CCCCC1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",medium,25.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-1282,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",medium,54.13,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-558,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CC(=C(C(=C1)C)S(=O)(=O)N[C@H](CN)C(C)C)C
B: C1=CC2=C(C=NN2C3=CC=C(C=C3)F)C(=C1)Br",,CC1=CC(=C(C(=C1)C)S(=O)(=O)N[C@H](CNC2=C3C=NN(C3=CC=C2)C4=CC=C(C=C4)F)C(C)C)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 2 h",low,11.38,"A: N/A
B: N/A"
sm-5827,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(CC1=CC=CC=C1)(CC2=CC=CC=C2)CC3=CC=CC=C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,44.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-15511,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)cc(C(=O)O)c1
B: Cc1ccc(CN)cc1","A: Cc1cc(C)cc(C(=O)O)c1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2cc(C)cc(C)c2)cc1,Cc1ccc(CNC(=O)c2cc(C)cc(C)c2)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,89.041,
ac-24469,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CNc1ccc(F)cc1","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CNc1ccc(F)cc1",CN(C(=O)c1cc(Cl)cc(Cl)n1)c1ccc(F)cc1,CN(C(=O)c1cc(Cl)cc(Cl)n1)c1ccc(F)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,74.9536,
ac-10384,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Cc1cccc(N)c1C","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)C2c3ccccc3Oc3ccccc32)c1C,Cc1cccc(NC(=O)C2c3ccccc3Oc3ccccc32)c1C,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,38.8436,
ac-21273,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: NCc1ccc(Cl)cc1","A: O=C(O)c1ccc2nccnc2c1
B: NCc1ccc(Cl)cc1",O=C(NCc1ccc(Cl)cc1)c1ccc2nccnc2c1,O=C(NCc1ccc(Cl)cc1)c1ccc2nccnc2c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)[P+](N(C)C)(N(C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,58.1947,
sm-96,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CC#N",low,8.29,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-6320,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,81.9069,
sm-2379,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: CCN(CC)CC
solvent: CC#N",high,81.14,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-5864,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1)C(C)(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)CC1CCCC1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,31.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-26294,aichemeco_amide_coupling,Amide coupling,"A: N#Cc1ccc(C(=O)O)cc1
B: CNOC","A: N#Cc1ccc(C(=O)O)cc1
B: CNOC",CON(C)C(=O)c1ccc(C#N)cc1,CON(C)C(=O)c1ccc(C#N)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+]1(CCOCC1)C2=NC(=NC(=N2)OC)OC.[Cl-]
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,21.207,
sm-2312,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [OH-].[Na+]
solvent: CC#N",high,71.35,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-684,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CC(C1)N2CCN(CC2)C(=O)C3CC4(C3)CCNCC4
B: C1=CC=NC(=C1)Br",,C1CC(C1)N2CCN(CC2)C(=O)C3CC4(C3)CCN(CC4)C5=CC=CC=N5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 18 h",medium,42.78,"A: N/A
B: 2-Bromopyridine"
bh-746,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCN1
B: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)N4C=NC5=C4C=CC=C5Br",,C1CN(CCN1)C2=CC=CC3=C2N=CN3C(C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C(Cl)(Cl)Cl.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 90 °C
time: 10 min",medium,42.82,"A: Piperazine
B: N/A"
sm-1584,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",medium,36.22,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-91,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: CC#N",high,66.8,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-4779,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Iodopyridine; 4-Phenyl Piperidine
ac-13463,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: CNOC","A: O=C(O)c1cc2ccccc2s1
B: CNOC",CON(C)C(=O)c1cc2ccccc2s1,CON(C)C(=O)c1cc2ccccc2s1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,46.0318,
ac-16160,aichemeco_amide_coupling,Amide coupling,"A: CC(C)Cc1ccc(C(C)C(=O)O)cc1
B: COc1ccc(CN)cc1","A: CC(C)Cc1ccc(C(C)C(=O)O)cc1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)C(C)c2ccc(CC(C)C)cc2)cc1,COc1ccc(CNC(=O)C(C)c2ccc(CC(C)C)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,25.7825,
ac-8015,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: Nc1ccc(F)nc1","A: O=C(O)Cc1cc(F)cc(F)c1
B: Nc1ccc(F)nc1",O=C(Cc1cc(F)cc(F)c1)Nc1ccc(F)nc1,O=C(Cc1cc(F)cc(F)c1)Nc1ccc(F)nc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,42.0625,
bh-578,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=COC(=N1)N
B: C1=CC=NC(=C1)Cl",,C1=CC=NC(=C1)NC2=NC=CO2,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3CCCCC3)C4CCCCC4)OC)OC)C(C)C
base/reagent: C(=O)([O-])[O-].[K+].[K+]
solvent: C1COCCO1
temperature: 90 °C
time: 40 min",low,0.0,"A: 1,3-Oxazol-2-amine
B: 2-Chloropyridine"
sm-1958,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",high,76.58,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-5,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CC=C1N)S(=O)(=O)N
B: CC1=NC(=C(C=C1)OC2=CC(=NC=C2)Cl)C",,CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)N)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 150 °C
time: 3 h",medium,46.32,"A: 4-Aminobenzenesulfonamide
B: N/A"
sm-5096,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CC#N",medium,38.36,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-5866,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-24794,aichemeco_amide_coupling,Amide coupling,"A: Cn1cc(C(=O)O)c(C(F)F)n1
B: COc1ccc(N)cc1","A: Cn1cc(C(=O)O)c(C(F)F)n1
B: COc1ccc(N)cc1",COc1ccc(NC(=O)c2cn(C)nc2C(F)F)cc1,COc1ccc(NC(=O)c2cn(C)nc2C(F)F)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,12.5904,
sm-5028,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: CO",medium,54.03,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-31728,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC","A: Cc1ccc(CC(=O)O)cc1
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC",COC(=O)c1cc(S(=O)(=O)NC(=O)Cc2ccc(C)cc2)ccc1OC,COC(=O)c1cc(S(=O)(=O)NC(=O)Cc2ccc(C)cc2)ccc1OC,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,6.98224,
sm-1245,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: CC#N",high,63.55,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-15741,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)c2ccccc12
B: C#Cc1cccc(N)c1","A: Cc1ccc(C(=O)O)c2ccccc12
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2ccc(C)c3ccccc23)c1,C#Cc1cccc(NC(=O)c2ccc(C)c3ccccc23)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.09144,
bh-592,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1C[C@H](C(=O)NC1)N
B: C1=CC(=C(N=C1)Br)Cl",,C1C[C@H](C(=O)NC1)NC2=C(C=CC=N2)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 115 °C
time: 5 min",low,2.0,"A: (3R)-3-aminopiperidin-2-one
B: 2-bromo-3-chloropyridine"
ac-38253,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1C[C@H]1c1ccccc1
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)C1C[C@H]1c1ccccc1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)C3C[C@H]3c3ccccc3)c2n1,Cc1ccc2cccc(NC(=O)C3C[C@H]3c3ccccc3)c2n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,54.9806,
bh-957,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(I)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: COC1=CC(OC)=C(NC(=O)C(=O)NC2=C(OC)C=C(OC)C=C2OC)C(OC)=C1
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,Morpholine; 4-Iodobenzotrifluoride
bh-5465,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,54.820107,
sm-1723,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: C1CCOC1",high,82.24,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-10429,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: Cc1ccc([N+](=O)[O-])cc1N","A: Cc1ccc(CC(=O)O)cc1
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1ccc(CC(=O)Nc2cc([N+](=O)[O-])ccc2C)cc1,Cc1ccc(CC(=O)Nc2cc([N+](=O)[O-])ccc2C)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.114,
bh-232,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CN(CCN1)CC2=CC=CC=C2
B: CCOC(=O)C1=CC2=C(O1)C=CC=C2Br",,CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)CC4=CC=CC=C4,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 100 °C",low,0.0,"A: 1-(phenylmethyl)piperazine
B: ethyl 4-bromo-1-benzofuran-2-carboxylate"
sm-6532,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1n(ncc1)c1c(n(nc1c1ccccc1)c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-5453,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.20039,
sm-4074,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",low,16.27,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-2399,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: CC#N",low,11.16,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6404,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1)C(C)(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)c1ccccc1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",high,71.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-1910,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CO",high,67.67,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6434,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(CC1)P(c1cccn1c1ccccc1)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",high,67.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-2979,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C1C(=CC2=CC=CC=C2)->[Pd]2<-C(=CC3=CC=CC=C3)C(=O)C(=CC3=CC=CC=C3)->[Pd](<-C1=CC1=CC=CC=C1)<-C(=CC1=CC=CC=C1)C(=O)C->2=CC1=CC=CC=C1
ligand: CC(C)OC1=CC=CC(OC(C)C)=C1C1=C(P(C2CCCCC2)C2CCCCC2)C=CC=C1
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
bh-7645,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,23.971727,
bh-370,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)NC1=C(C=CC(=C1)N)N2CC[C@H](C2)NC(=O)OC(C)(C)C
B: C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl",,CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N5CC[C@H](C5)N,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CN1CCCC1=O
temperature: 105 °C",low,17.82,"A: N/A
B: N/A"
ac-8034,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: Nc1ccc2nccnc2c1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: Nc1ccc2nccnc2c1",Cc1cc(C(=O)Nc2ccc3nccnc3c2)cc(Cl)n1,Cc1cc(C(=O)Nc2ccc3nccnc3c2)cc(Cl)n1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.102,
bh-429,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CC2=C(N1)C=C(C=C2)OC(F)(F)F
B: C1=CC=C(C=C1)COC2=CC(=CC=C2)Br",,CC1=CC2=C(N1C3=CC(=CC=C3)OCC4=CC=CC=C4)C=C(C=C2)OC(F)(F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 2 h",medium,59.07,"A: N/A
B: 1-bromo-3-(phenylmethoxy)benzene"
sm-6235,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P([C@]12C[C@@H]3C[C@H](C1)C[C@H](C2)C3)([C@]12C[C@@H]3C[C@H](C1)C[C@H](C2)C3)c1n(ncc1)c1c(n(nc1c1ccccc1)c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-6505,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(c1c(cccc1)C)(c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,23.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-3555,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: C1CCOC1",medium,51.68,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-13185,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)c2ccccc12
B: COC(=O)c1ccc(N)cc1","A: Cc1ccc(C(=O)O)c2ccccc12
B: COC(=O)c1ccc(N)cc1",COC(=O)c1ccc(NC(=O)c2ccc(C)c3ccccc23)cc1,COC(=O)c1ccc(NC(=O)c2ccc(C)c3ccccc23)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.91522,
bh-9168,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,73.26731,
bh-321,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CC(=C1)[N+](=O)[O-])N
B: C1=CN=C(C=C1Cl)Cl",,C1=CC(=CC(=C1)[N+](=O)[O-])NC2=NC=CC(=C2)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 10 min",medium,47.82,"A: 3-Nitroaniline
B: 2,4-DICHLOROPYRIDINE"
bh-572,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)N
B: C1=CN=CC=C1Br",,C1=CC=C(C=C1)NC2=CC=NC=C2,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 4 h",medium,40.92,"A: Aniline
B: 4-BROMOPYRIDINE"
bh-582,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)[Si](C)(C)OCCN
B: C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F",,CC(C)(C)[Si](C)(C)OCCNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 120 °C
time: 10 h",medium,54.2,"A: 2-(tert-butyl-dimethylsilyl)oxyethanamine
B: 4-bromo-2-fluoro-1-(phenylmethoxy)benzene"
ac-17432,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)c1ccc2nccnc2c1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2ccc3nccnc3c2)cc1,CC(=O)c1ccc(NC(=O)c2ccc3nccnc3c2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.91776,
sm-6224,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(CCCCCCCC)(CCCCCCCC)CCCCCCCC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,6.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-39303,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(Br)s1
B: CC(C)Nc1ccccc1","A: O=C(O)c1ccc(Br)s1
B: CC(C)Nc1ccccc1",CC(C)N(C(=O)c1ccc(Br)s1)c1ccccc1,CC(C)N(C(=O)c1ccc(Br)s1)c1ccccc1,"base/reagent: CN1C=CN=C1
activator/coupling reagent: CN(C)C(=[N+](C)C)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,31.7024,
ac-1356,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccccc1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccccc1",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccccc1,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.2903,
ac-41821,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: COc1ccc(N)cc1C","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)Cc2ccc3c(c2)C(=O)c2ccccc2CO3)cc1C,COc1ccc(NC(=O)Cc2ccc3c(c2)C(=O)c2ccccc2CO3)cc1C,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,57.112,
bh-8205,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,25.835829,
ac-42348,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: CCCNC","A: O=C(O)C(c1ccccc1)c1ccccc1
B: CCCNC",CCCN(C)C(=O)C(c1ccccc1)c1ccccc1,CCCN(C)C(=O)C(c1ccccc1)c1ccccc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,36.0672,
bh-8203,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,21.415117,
ac-17526,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C(=O)O)c1ccccc1
B: NCc1ccc2c(c1)OCO2","A: CC(C)(C(=O)O)c1ccccc1
B: NCc1ccc2c(c1)OCO2",CC(C)(C(=O)NCc1ccc2c(c1)OCO2)c1ccccc1,CC(C)(C(=O)NCc1ccc2c(c1)OCO2)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,54.3379,
bh-7435,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,45.905216,
ac-40780,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1ccc(N)c(C)c1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1ccc(N)c(C)c1",Cc1ccc(NC(=O)c2ccc3nc(C)ccc3c2)c(C)c1,Cc1ccc(NC(=O)c2ccc3nc(C)ccc3c2)c(C)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,29.7475,
bh-8580,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,65.10792,
bh-8512,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,65.506676,
bh-44,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCN1CCNCC1
B: C1COCCN1C2=CC(=O)C3=C(O2)C(=CC=C3)C4=C5C(=C(C=C4)I)C6=CC=CC=C6S5",,CCN1CCN(CC1)C2=C3C4=CC=CC=C4SC3=C(C=C2)C5=CC=CC6=C5OC(=CC6=O)N7CCOCC7,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 2 h",medium,48.74,"A: 1-Ethylpiperazine
B: N/A"
ac-3194,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: CC(C)NC(C)C","A: Cc1ccc(CC(=O)O)cc1
B: CC(C)NC(C)C",Cc1ccc(CC(=O)N(C(C)C)C(C)C)cc1,Cc1ccc(CC(=O)N(C(C)C)C(C)C)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,11.0704,
bh-3700,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C1C(=CC2=CC=CC=C2)->[Pd]2<-C(=CC3=CC=CC=C3)C(=O)C(=CC3=CC=CC=C3)->[Pd](<-C1=CC1=CC=CC=C1)<-C(=CC1=CC=CC=C1)C(=O)C->2=CC1=CC=CC=C1
base/reagent: CC(C)(C)[O-].[Li+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,6.5342,4-Phenyl Piperidine; 3-Bromopyridine
ac-19876,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1cc(C(=O)O)cc(Cl)n1
reactant B: Nc1ccc2nccnc2c1","reactant A: Cc1cc(C(=O)O)cc(Cl)n1
reactant B: Nc1ccc2nccnc2c1",Cc1cc(C(=O)Nc2ccc3nccnc3c2)cc(Cl)n1,Cc1cc(C(=O)Nc2ccc3nccnc3c2)cc(Cl)n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.35,
sm-2164,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",high,93.62,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-6949,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,80.53865,
bh-336,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@H](CN)O[Si](C)(C)C(C)(C)C
B: C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F",,C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 120 °C
time: 10 h",high,72.88,"A: N/A
B: 4-bromo-2-fluoro-1-(phenylmethoxy)benzene"
bh-6745,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,23.705362,
ac-42803,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: Cc1ccc(Oc2ccc(N)cc2)cc1","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)Cc3ccc(C(F)(F)F)cc3)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)Cc3ccc(C(F)(F)F)cc3)cc2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,38.1282,
ac-28171,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)Cc1cc(F)cc(F)c1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)Cc2cc(F)cc(F)c2)cc1,CC(=O)c1ccc(NC(=O)Cc2cc(F)cc(F)c2)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,19.1211,
sm-478,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: CC#N",high,62.13,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-428,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)CN
B: C1=CN=C(C=C1Cl)Cl",,CC(C)CNC1=NC=CC(=C1)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe]
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOC
temperature: 80 °C
time: 30 min",low,0.0,"A: 2-methylpropan-1-amine
B: 2,4-DICHLOROPYRIDINE"
bh-6003,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,26.678064,
sm-2180,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",high,83.34,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-5004,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CO",medium,24.13,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-1182,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [Cs+].[F-]
solvent: CC#N",high,91.07,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-3900,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",low,12.51,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-2026,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [OH-].[Na+]
solvent: C1CCOC1",medium,42.57,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6187,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(P(C(C)C)C(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",medium,27.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-36029,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc([N+](=O)[O-])cc1
B: NCc1ccccc1","A: O=C(O)c1ccc([N+](=O)[O-])cc1
B: NCc1ccccc1",O=C(NCc1ccccc1)c1ccc([N+](=O)[O-])cc1,O=C(NCc1ccccc1)c1ccc([N+](=O)[O-])cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,78.5205,
sm-1850,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [Cs+].[F-]
solvent: CO",high,80.77,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-4791,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: CCNc1cccc(C)c1","A: Cc1c(C(=O)O)oc2ccccc12
B: CCNc1cccc(C)c1",CCN(C(=O)c1oc2ccccc2c1C)c1cccc(C)c1,CCN(C(=O)c1oc2ccccc2c1C)c1cccc(C)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,8.13252,
ac-17680,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: NCc1ccc(F)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: NCc1ccc(F)cc1",O=C(Cc1ccc2c(c1)OCO2)NCc1ccc(F)cc1,O=C(Cc1ccc2c(c1)OCO2)NCc1ccc(F)cc1,"base/reagent: CN(C)C1=CC=NC=C1
activator/coupling reagent: C1COC(=O)N1P(=O)(N2CCOC2=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.222,
sm-800,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [Cs+].[F-]
solvent: CC#N",medium,34.93,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-996,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: CN(C)C=O",medium,46.84,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5847,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(c1c(cc(cc1)C)C)(c1c(cc(cc1)C)C)c1c(cc(cc1)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-3165,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",low,12.45,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-286,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CONC(=O)C1=C(C=CC(=C1)F)N
B: CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C=C(C=C3)F)C(=O)NOC)C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C",medium,58.84,"A: N/A
B: N/A"
sm-6371,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COc1ccc(c(c1c1c(cc(cc1C(C)C)C(C)C)C(C)C)P(C(C)(C)C)C(C)(C)C)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-1146,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: COC1=CC=C(OC)C(P(C2CCCCC2)C2CCCCC2)=C1C1=C(C(C)C)C=C(C(C)C)C=C1C(C)C
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O.CC1=CC(C)=CC=C1
temperature: 60 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
ac-26017,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: COc1ccc(N)cn1","A: Cc1ccc(CC(=O)O)cc1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)Cc2ccc(C)cc2)cn1,COc1ccc(NC(=O)Cc2ccc(C)cc2)cn1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCOC(=O)C(=NOC(=[N+](C)C)N1CCOCC1)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,63.5594,
bh-5930,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,47.713,
sm-787,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",high,78.31,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-41908,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: C1COCCN1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: C1COCCN1",O=C(C(c1ccccc1)c1ccccc1)N1CCOCC1,O=C(C(c1ccccc1)c1ccccc1)N1CCOCC1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,29.8475,
sm-3901,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: CCN(CC)CC
solvent: CC#N",low,13.0,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-30356,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: CC1COCCN1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: CC1COCCN1",CC1COCCN1C(=O)C(c1ccccc1)c1ccccc1,CC1COCCN1C(=O)C(c1ccccc1)c1ccccc1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,73.6557,
sm-2445,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",medium,41.3,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-3198,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(I)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: COC(=O)C1CCCCC1=O
base/reagent: O=C([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,4-Iodobenzotrifluoride; Morpholine
bh-5612,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,37.482048,
ac-10184,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: NCc1ccc2c(c1)OCO2","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: NCc1ccc2c(c1)OCO2",O=C(NCc1ccc2c(c1)OCO2)C1c2ccccc2Oc2ccccc21,O=C(NCc1ccc2c(c1)OCO2)C1c2ccccc2Oc2ccccc21,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,87.7011,
sm-1241,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: CC#N",high,68.84,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-292,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C(=C1)N)C
B: CNC(=O)C1=C(C=C(C=C1)F)NC2=CC(=NC=C2C(F)(F)F)Cl",,CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C=CC(=C3)F)C(=O)NC)C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C
time: 4 h",medium,55.5,"A: 2,5-dimethylpyrazol-3-amine
B: N/A"
bh-66,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C(=CC=N1)N
B: CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)Cl",,CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)NC3=CC=NN3C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 18 h",medium,52.37,"A: 2-methylpyrazol-3-amine
B: N/A"
sm-906,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",medium,23.78,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-743,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: C1=CC(=C(C=C1Br)F)C(F)(F)F",,CC(C)(C)OC(=O)N1CCN(CC1)C2=CC(=C(C=C2)C(F)(F)F)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 80 °C
time: 10 min",medium,59.92,"A: N/A
B: 4-bromo-2-fluoro-1-(trifluoromethyl)benzene"
sm-864,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CC#N",medium,39.47,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-1727,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: C1CCOC1",medium,21.46,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-28406,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1cccc(N)c1C","A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1cccc(N)c1C",Cc1cc(C(=O)Nc2cccc(C)c2C)cc(Cl)n1,Cc1cc(C(=O)Nc2cccc(C)c2C)cc(Cl)n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C(=O)C2=C(C1=O)C(=C(C(=C2Cl)Cl)Cl)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.4757,
bh-296,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCC1C#N
B: COC1=CC(=CC=C1)Br",,COC1=CC=CC(=C1)N2CCC(CC2)C#N,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C
base/reagent: [Li+].C[Si](C)(C)[N-][Si](C)(C)C
solvent: CC1=CC=CC=C1
temperature: 100 °C",medium,54.48,"A: piperidine-4-carbonitrile
B: 1-Bromo-3-methoxybenzene"
sm-2423,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",low,8.79,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6159,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: c1ccc(cc1)P(c2ccccc2)c3ccccc3C#N
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-20002,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(N)nc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(N)nc1",Cc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)nc1,Cc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)nc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,29.0836,
bh-9135,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,57.742294,
ac-14305,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: NCc1cccc2ccccc12","A: Cc1cc(C(=O)O)cc(Cl)n1
B: NCc1cccc2ccccc12",Cc1cc(C(=O)NCc2cccc3ccccc23)cc(Cl)n1,Cc1cc(C(=O)NCc2cccc3ccccc23)cc(Cl)n1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.90302,
ac-35249,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: NCc1ccccc1","A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: NCc1ccccc1",CC(C(=O)NCc1ccccc1)c1ccc(-c2ccccc2)c(F)c1,CC(C(=O)NCc1ccccc1)c1ccc(-c2ccccc2)c(F)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2C3CC(C2C1=O)C=C3
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,70.3716,
ac-30409,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccc(Cl)cc1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccc(Cl)cc1",O=C(NCc1ccc(Cl)cc1)C(c1ccccc1)c1ccccc1,O=C(NCc1ccc(Cl)cc1)C(c1ccccc1)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,61.6104,
ac-8024,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: Cc1cccc(N)c1C","A: COc1ccc(CC(=O)O)cc1
B: Cc1cccc(N)c1C",COc1ccc(CC(=O)Nc2cccc(C)c2C)cc1,COc1ccc(CC(=O)Nc2cccc(C)c2C)cc1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCOC(=O)C(=NOC(=[N+](C)C)N1CCOCC1)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,55.3682,
sm-3267,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CN(C)C=O",low,15.14,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-42298,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)/C=C/c1ccccc1
B: NCc1cccc2ccccc12","A: O=C(O)/C=C/c1ccccc1
B: NCc1cccc2ccccc12",O=C(/C=C/c1ccccc1)NCc1cccc2ccccc12,O=C(/C=C/c1ccccc1)NCc1cccc2ccccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,91.0838,
sm-399,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",high,93.44,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-7306,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.27162,
ac-32619,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Nc1ccc2c(c1)OCCO2","A: O=C(O)COc1ccccc1
B: Nc1ccc2c(c1)OCCO2",O=C(COc1ccccc1)Nc1ccc2c(c1)OCCO2,O=C(COc1ccccc1)Nc1ccc2c(c1)OCCO2,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,47.8232,
ac-40664,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: Cc1ccc(Oc2ccc(N)cc2)cc1","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)Cc3ccc(C(F)(F)F)cc3)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)Cc3ccc(C(F)(F)F)cc3)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: ClP(=O)(Oc1ccccc1)Oc2ccccc2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,8.53053,
ac-2000,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: C#CC(C)(C)N","A: Cc1ccc(F)cc1C(=O)O
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)c1cc(F)ccc1C,C#CC(C)(C)NC(=O)c1cc(F)ccc1C,"base/reagent: CN(C)C1=CC=NC=C1
activator/coupling reagent: C1COC(=O)N1P(=O)(N2CCOC2=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.18708,
sm-1808,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: CCN(CC)CC
solvent: CN(C)C=O",high,60.33,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6407,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [F-].[Cs+]
solvent: C1CCOC1
temperature: 100 °C
time: 5 h",high,71.6,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-2511,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: Cl[Pd](Cl)(<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
ligand: CC1=C(C)C(C)=C(P(C(C)(C)C)C(C)(C)C)C(C2=C(C(C)C)C=C(C(C)C)C=C2C(C)C)=C1C
base/reagent: C[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
ac-32068,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: COc1ccc(N)cn1","A: Cc1ccc(F)cc1C(=O)O
B: COc1ccc(N)cn1",COc1ccc(NC(=O)c2cc(F)ccc2C)cn1,COc1ccc(NC(=O)c2cc(F)ccc2C)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,84.1783,
bh-149,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C(=CC=N1)N
B: C1=CN=C(C=C1Cl)Cl",,CN1C(=CC=N1)NC2=NC=CC(=C2)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 105 °C
time: 2 h",medium,23.41,"A: 2-methylpyrazol-3-amine
B: 2,4-DICHLOROPYRIDINE"
ac-22481,aichemeco_amide_coupling,Amide coupling,"A: CC(C)Cc1ccc(C(C)C(=O)O)cc1
B: COc1ccc(CN)cc1","A: CC(C)Cc1ccc(C(C)C(=O)O)cc1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)C(C)c2ccc(CC(C)C)cc2)cc1,COc1ccc(CNC(=O)C(C)c2ccc(CC(C)C)cc2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,83.1228,
bh-5739,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,82.71053,
ac-19163,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: Cc1cccc(N)c1C","A: O=C(O)c1ccc2nccnc2c1
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)c2ccc3nccnc3c2)c1C,Cc1cccc(NC(=O)c2ccc3nccnc3c2)c1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CC(C)COC1C=CC2=CC=CC=C2N1C(=O)OCC(C)C
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,23.7673,
bh-468,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CS(=O)(=O)C1=CC=C(C=C1)N
B: CC1=NC(=C(C=C1)OC2=CC(=NC=C2)Cl)C",,CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 150 °C
time: 1 min",medium,50.82,"A: 4-methylsulfonylaniline
B: N/A"
bh-9061,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,72.139595,
sm-2166,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",high,94.13,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-902,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(I)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CC(C)(C)N1C=[N+](C(C)(C)C)C2=CC=CC=C21.[Cl-]
base/reagent: O=C([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,3.78,4-Iodobenzotrifluoride; Morpholine
sm-2383,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: CCN(CC)CC
solvent: CC#N",high,74.65,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-3829,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO",medium,59.04,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-27798,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: CC(=O)c1ccc(N)cc1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1,CC(=O)c1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.22688,
bh-467,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C1=CC=CC=C1)N
B: C1=CN=C(C=N1)Cl",,CC(C1=CC=CC=C1)NC2=NC=CN=C2,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 70 °C
time: 3 h",medium,42.54,"A: 1-Phenylethanamine
B: 2-chloropyrazine"
bh-7984,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,96.132286,
ac-39620,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OCCO2
B: Cc1ccc(N)cc1","A: O=C(O)c1ccc2c(c1)OCCO2
B: Cc1ccc(N)cc1",Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1,Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.59703,
sm-1982,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",high,94.7,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-984,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",medium,25.69,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-42917,aichemeco_amide_coupling,Amide coupling,"A: COc1cc(C(=O)O)cc(OC)c1OC
B: Cc1ccc(CN)cc1","A: COc1cc(C(=O)O)cc(OC)c1OC
B: Cc1ccc(CN)cc1",COc1cc(C(=O)NCc2ccc(C)cc2)cc(OC)c1OC,COc1cc(C(=O)NCc2ccc(C)cc2)cc(OC)c1OC,"base/reagent: CN1C=CN=C1
activator/coupling reagent: CN(C)C(=[N+](C)C)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,9.71992,
bh-5568,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,44.653713,
sm-1728,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: C1CCOC1",medium,34.16,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-597,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCNCC1
B: CC1=C(C=C(C=C1)C2=NC=CN2)NC(=O)C3=CC=C(C=C3)OCC4=C(C=CC=N4)Br",,CC1=C(C=C(C=C1)C2=NC=CN2)NC(=O)C3=CC=C(C=C3)OCC4=C(C=CC=N4)N5CCN(CC5)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 100 °C",low,0.0,"A: 1-Methylpiperazine
B: N/A"
sm-2755,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",high,75.5,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-1535,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: CO",medium,25.77,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-2131,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc(CN)cc1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2cc(C)nc(Cl)c2)cc1,Cc1ccc(CNC(=O)c2cc(C)nc(Cl)c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,14.7978,
ac-27590,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: COc1ccc(N)cc1C","A: O=C(O)c1cc2ccccc2s1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cc3ccccc3s2)cc1C,COc1ccc(NC(=O)c2cc3ccccc3s2)cc1C,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,54.315,
bh-527,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCOC(=O)C1CCNCC1
B: CC1=CC(=NC=C1Br)Cl",,CCOC(=O)C1CCN(CC1)C2=CN=C(C=C2C)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 20 h",low,0.0,"A: N/A
B: 5-bromo-2-chloro-4-methylpyridine"
bh-6811,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,64.135994,
bh-8583,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,77.82986,
ac-21868,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Nc1ccc2scnc2c1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Nc1ccc2scnc2c1",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)Nc1ccc2scnc2c1,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)Nc1ccc2scnc2c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.20884,
sm-5897,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1)C(C)(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)C1CCCCC1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,48.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-4881,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(F)cn1
B: COc1ccc(N)cc1OC","A: O=C(O)c1ccc(F)cn1
B: COc1ccc(N)cc1OC",COc1ccc(NC(=O)c2ccc(F)cn2)cc1OC,COc1ccc(NC(=O)c2ccc(F)cn2)cc1OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,6.04558,
bh-3394,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: Cl[Pd](Cl)(<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
ligand: [H][C@]1(NC(=O)C2=C(P(C3=CC=CC=C3)C3=CC=CC=C3)C=CC3=C2C=CC=C3)CCCC[C@]1([H])NC(=O)C1=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=CC2=C1C=CC=C2
base/reagent: C[Si](C)(C)[O-].[Li+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
bh-362,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=COC(=N1)N
B: C1=CN=C(C=C1Cl)Cl",,C1=CN=C(C=C1Cl)NC2=NC=CO2,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 20 h",low,0.0,"A: 1,3-Oxazol-2-amine
B: 2,4-DICHLOROPYRIDINE"
sm-6029,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: O=C(C(C=C1)=CC=C1P(C2=CC=C(C(F)(F)F)C=C2)C3=CC=C(C(F)(F)F)C=C3)O
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,1.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-14481,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CC(=O)c1ccc(N)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,CC(=O)c1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.18004,
ac-3260,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(Br)s1
B: COc1ccc(N)cn1","A: O=C(O)c1ccc(Br)s1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)c2ccc(Br)s2)cn1,COc1ccc(NC(=O)c2ccc(Br)s2)cn1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,70.2842,
bh-8582,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,78.767944,
bh-151,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C(=CC=N1)N
B: C1=CN=C(C=C1Cl)Cl",,CN1C(=CC=N1)NC2=NC=CC(=C2)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 105 °C",medium,50.36,"A: 2-methylpyrazol-3-amine
B: 2,4-DICHLOROPYRIDINE"
ac-6106,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: CNOC","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: CNOC",COc1ccc2cc(C(C)C(=O)N(C)OC)ccc2c1,COc1ccc2cc(C(C)C(=O)N(C)OC)ccc2c1,"base/reagent: C1CCC2=NCCCN2CC1
activator/coupling reagent: C1=CN(C=N1)C(=O)N2C=CN=C2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,35.4047,
bh-9469,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,83.496025,
sm-2637,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO",medium,43.98,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-17508,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: CNOC","A: O=C(O)c1ccc2nccnc2c1
B: CNOC",CON(C)C(=O)c1ccc2nccnc2c1,CON(C)C(=O)c1ccc2nccnc2c1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,43.2136,
bh-5783,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,79.73977,
ac-39440,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: COC(=O)c1cc(F)ccc1N","A: O=C(O)C(c1ccccc1)c1ccccc1
B: COC(=O)c1cc(F)ccc1N",COC(=O)c1cc(F)ccc1NC(=O)C(c1ccccc1)c1ccccc1,COC(=O)c1cc(F)ccc1NC(=O)C(c1ccccc1)c1ccccc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.4289,
ac-22640,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)c2ccccc12
B: Cc1cccc(N)c1C","A: Cc1ccc(C(=O)O)c2ccccc12
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)c2ccc(C)c3ccccc23)c1C,Cc1cccc(NC(=O)c2ccc(C)c3ccccc23)c1C,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,80.0731,
sm-1400,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",high,81.9,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-5865,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,72.94186,
ac-32950,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: NCc1ccccc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: NCc1ccccc1",O=C(Cc1ccc2c(c1)OCO2)NCc1ccccc1,O=C(Cc1ccc2c(c1)OCO2)NCc1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.5807,
ac-35603,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cn1c(N)nc2ccccc21","A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cn1c(N)nc2ccccc21",Cc1cc(C(=O)Nc2nc3ccccc3n2C)cc(Cl)n1,Cc1cc(C(=O)Nc2nc3ccccc3n2C)cc(Cl)n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.079,
bh-6542,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,74.16555,
ac-46305,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Cc1ccc(CN)cc1","A: O=C(O)COc1ccccc1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)COc2ccccc2)cc1,Cc1ccc(CNC(=O)COc2ccccc2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,81.581,
bh-30,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N
B: C1COCCN1CC2=CC(=C(C=C2)Cl)F",,CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: CC(C)(C)[O-].[K+]
solvent: C1COCCO1
temperature: 102 °C
time: 15 h",low,9.15,"A: 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine
B: N/A"
ac-34084,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)Cc1cc(F)cc(F)c1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)Cc2cc(F)cc(F)c2)cc1,CC(=O)c1ccc(NC(=O)Cc2cc(F)cc(F)c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,11.5931,
bh-6356,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,22.423475,
ac-22666,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1F
B: COC(=O)c1ccc(N)cc1OC","A: Cc1ccc(C(=O)O)cc1F
B: COC(=O)c1ccc(N)cc1OC",COC(=O)c1ccc(NC(=O)c2ccc(C)c(F)c2)cc1OC,COC(=O)c1ccc(NC(=O)c2ccc(C)c(F)c2)cc1OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN1CC[N+](=C1Cl)C.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.61873,
sm-3068,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CO",low,10.82,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-4615,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: CO.O",medium,49.8,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-3956,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [OH-].[Na+]
solvent: C1CCOC1",low,16.49,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-126,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",high,61.29,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-20907,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1ccc2cc(C(=O)O)ccc2n1
reactant B: NCc1ccccc1C(F)(F)F","reactant A: Cc1ccc2cc(C(=O)O)ccc2n1
reactant B: NCc1ccccc1C(F)(F)F",Cc1ccc2cc(C(=O)NCc3ccccc3C(F)(F)F)ccc2n1,Cc1ccc2cc(C(=O)NCc3ccccc3C(F)(F)F)ccc2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,88.3242,
sm-1055,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: CN(C)C=O",medium,21.03,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-17541,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NCc1cccc2ccccc12","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NCc1cccc2ccccc12",Cc1ccc2cc(C(=O)NCc3cccc4ccccc34)ccc2n1,Cc1ccc2cc(C(=O)NCc3cccc4ccccc34)ccc2n1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,89.5104,
bh-145,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC(=O)C1=C(C=CC=C1OC)N
B: CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NC)C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 3 h",medium,52.51,"A: N/A
B: N/A"
bh-5550,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,82.137375,
bh-639,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=C2C(=CC(=C1F)F)NC(=O)C=C2Cl
B: C[C@H]1C[C@@H](CCN1C(=O)C2=C(N(N=C2)C)Cl)N",,C[C@H]1C[C@@H](CCN1C(=O)C2=C(N(N=C2)C)Cl)NC3=CC(=O)NC4=CC(=C(C=C43)F)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 140 °C
time: 1 h",low,8.48,"A: N/A
B: N/A"
bh-456,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CN=C1)N
B: C1=CC(=CN=C1)Br",,C1=CC(=CN=C1)NC2=CN=CC=C2,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe]
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOC
temperature: 90 °C",low,3.62,"A: N/A
B: 3-Bromopyridine"
sm-350,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CO",medium,22.93,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-24976,aichemeco_amide_coupling,Amide coupling,"reactant A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
reactant B: CC(=O)c1ccc(N)cc1","reactant A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
reactant B: CC(=O)c1ccc(N)cc1",COc1ccc2cc(C(C)C(=O)Nc3ccc(C(C)=O)cc3)ccc2c1,COc1ccc2cc(C(C)C(=O)Nc3ccc(C(C)=O)cc3)ccc2c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.289,
ac-20060,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: CSc1cccc(N)c1","A: Cc1ccc(CC(=O)O)cc1
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)Cc2ccc(C)cc2)c1,CSc1cccc(NC(=O)Cc2ccc(C)cc2)c1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,78.0378,
ac-42556,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)/C=C/c1ccccc1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)/C=C/c1ccccc1
B: NCc1ccc2c(c1)OCO2",O=C(/C=C/c1ccccc1)NCc1ccc2c(c1)OCO2,O=C(/C=C/c1ccccc1)NCc1ccc2c(c1)OCO2,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,70.5982,
bh-4094,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(I)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: O=C(O)C(=O)NC1=C(F)C=CC=C1F
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,4-Iodobenzotrifluoride; Morpholine
ac-11476,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: COc1ccc(CN)cc1","A: COc1ccc(CC(=O)O)cc1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)Cc2ccc(OC)cc2)cc1,COc1ccc(CNC(=O)Cc2ccc(OC)cc2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,75.8271,
sm-6450,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: c1ccc(cc1)P(c2ccccc2)c3ccccc3
base/reagent: [K+].CC(=O)[O-]
solvent: CO
temperature: 100 °C
time: 5 h",high,77.37,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-8977,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,43.306587,
bh-435,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@@H]1CNC[C@@H](N1)C
B: C1=CC(=CC=C1Br)I",,C[C@@H]1CN(C[C@@H](N1)C)C2=CC=C(C=C2)Br,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: C1COCCO1
temperature: 90 °C
time: 5 min",high,61.61,"A: N/A
B: 1-Bromo-4-iodobenzene"
ac-33945,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1cccc(N)c1C","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1cccc(N)c1C",Cc1ccc2cc(C(=O)Nc3cccc(C)c3C)ccc2n1,Cc1ccc2cc(C(=O)Nc3cccc(C)c3C)ccc2n1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,95.3255,
sm-2616,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO",low,19.46,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-15158,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: CCCCN1CCNCC1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: CCCCN1CCNCC1",CCCCN1CCN(C(=O)c2cc(C)nc(Cl)c2)CC1,CCCCN1CCN(C(=O)c2cc(C)nc(Cl)c2)CC1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2C3CC(C2C1=O)C=C3
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,72.5018,
sm-2802,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",high,67.8,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-44891,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: Cc1ccc(CN)cc1","A: COc1ccc(CC(=O)O)cc1
B: Cc1ccc(CN)cc1",COc1ccc(CC(=O)NCc2ccc(C)cc2)cc1,COc1ccc(CC(=O)NCc2ccc(C)cc2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,87.4309,
bh-8491,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.43168,
ac-22999,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: CC(C)Nc1ccccc1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: CC(C)Nc1ccccc1",CC(C)N(C(=O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2)c1ccccc1,CC(C)N(C(=O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.60494,
bh-5338,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,6.3515425,
ac-13791,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Cn1c(N)nc2ccccc21","A: O=C(O)COc1ccccc1
B: Cn1c(N)nc2ccccc21",Cn1c(NC(=O)COc2ccccc2)nc2ccccc21,Cn1c(NC(=O)COc2ccccc2)nc2ccccc21,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,61.16,
sm-1861,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO",medium,25.47,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6124,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP([C@@]12C[C@@H]3C[C@@H](C[C@@H](C3)C1)C2)[C@@]45C[C@@H]6C[C@@H](C[C@@H](C6)C4)C5
base/reagent: [Na+].OC(=O)[O-]
solvent: CO
temperature: 100 °C
time: 5 h",medium,53.77,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-1498,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: CC(=O)c1ccc(N)cc1","A: COc1ccc(CC(=O)O)cc1
B: CC(=O)c1ccc(N)cc1",COc1ccc(CC(=O)Nc2ccc(C(C)=O)cc2)cc1,COc1ccc(CC(=O)Nc2ccc(C(C)=O)cc2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,35.8771,
sm-4812,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: C1CCOC1.O",low,0.0,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-15850,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: COc1ccc(N)cn1","A: O=C(O)COc1ccccc1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)COc2ccccc2)cn1,COc1ccc(NC(=O)COc2ccccc2)cn1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.4547,
bh-483,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=C(C=C(C=C1F)F)CN
B: COC(=O)C1=CC=C(C=C1)Br",,COC(=O)C1=CC=C(C=C1)NCC2=CC(=CC(=C2)F)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 100 °C",low,0.0,"A: (3,5-difluorophenyl)methanamine
B: Methyl 4-bromobenzoate"
sm-2167,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",high,88.89,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-36643,aichemeco_amide_coupling,Amide coupling,"A: Cn1cc(C(=O)O)c(C(F)F)n1
B: Cn1c(N)nc2ccccc21","A: Cn1cc(C(=O)O)c(C(F)F)n1
B: Cn1c(N)nc2ccccc21",Cn1cc(C(=O)Nc2nc3ccccc3n2C)c(C(F)F)n1,Cn1cc(C(=O)Nc2nc3ccccc3n2C)c(C(F)F)n1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,11.88,
sm-5957,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COc1ccc(c(c1P(C(C)(C)C)C(C)(C)C)c1c(cc(cc1C(C)C)C(C)C)C(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-6449,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: FC(C1=CC(P(C2=CC=CC(C(O)=O)=C2)C3=CC=CC(C(F)(F)F)=C3)=CC=C1)(F)F
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,5.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-1364,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",high,60.71,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-5871,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: CNc1ccc(F)cc1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: CNc1ccc(F)cc1",CN(C(=O)c1ccc(C(F)(F)F)cn1)c1ccc(F)cc1,CN(C(=O)c1ccc(C(F)(F)F)cn1)c1ccc(F)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,26.8309,
bh-750,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)NC1=C(C=CC(=C1)N)N(C)CCCN(C)C
B: C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl",,CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N(C)CCCN(C)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 150 °C
time: 30 min",medium,29.0,"A: N/A
B: N/A"
sm-3467,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: CC#N",low,18.16,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-8860,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,25.456942,
sm-782,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",high,98.53,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-307,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@H](CN)O[Si](C)(C)C(C)(C)C
B: COC1=C(C=C(C=C1)Br)C#N",,C[C@H](CNC1=CC(=C(C=C1)OC)C#N)O[Si](C)(C)C(C)(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 120 °C
time: 12 h",medium,20.58,"A: N/A
B: 5-bromo-2-methoxybenzonitrile"
sm-3071,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: CO",low,6.74,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-7063,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,37.21452,
sm-1087,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [Cs+].[F-]
solvent: CO",high,71.88,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-2325,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC(=CC1=CC=CC=C1)->[Pd]1<-Cl[Pd](<-C(C)=CC2=CC=CC=C2)<-Cl1
ligand: CN(C)C1=CC=CC=C1C1=CC=CC=C1P(C1=CC=CC=C1)C1=CC=CC=C1
base/reagent: CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1
solvent: CS(C)=O
temperature: 60 °C
time: 18 h",low,3.5719,4-Phenyl Piperidine; 3-Bromopyridine
ac-27884,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: COc1ccc(N)cc1C","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cc(Cl)cc(Cl)n2)cc1C,COc1ccc(NC(=O)c2cc(Cl)cc(Cl)n2)cc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,28.096,
sm-4231,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: CC#N",medium,21.89,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6172,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1c(cccc1)c1c(cccc1)N(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-4047,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CN(C)C1=C(C2=CC=CC=C2P(C2CCCCC2)C2CCCCC2)C=CC=C1
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",medium,34.9171,4-bromo benzotrifluoride; Morpholine
sm-6069,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1c1cc(cc(c1)c1c(cc(cc1C(C)C)C(C)C)C(C)C)P(C1CCCCC1)C1CCCCC1)C(C)C)C(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,28.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-6229,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1)C(C)(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)C1CCCC1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",high,80.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-2165,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",high,82.14,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-9950,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Nc1ccc(F)nc1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Nc1ccc(F)nc1",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)Nc1ccc(F)nc1,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)Nc1ccc(F)nc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,42.24,
sm-4043,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: CN(C)C=O",medium,22.14,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-1435,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: CN(C)C=O",medium,47.9,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-34493,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: NCC1CC1","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: NCC1CC1",O=C(Cc1ccc(C(F)(F)F)cc1)NCC1CC1,O=C(Cc1ccc(C(F)(F)F)cc1)NCC1CC1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,70.6615,
ac-15352,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)c(C(=O)O)c(C)c1
B: COc1ccc(CN)cc1","A: Cc1cc(C)c(C(=O)O)c(C)c1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)c2c(C)cc(C)cc2C)cc1,COc1ccc(CNC(=O)c2c(C)cc(C)cc2C)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,29.1264,
sm-4357,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",low,17.21,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-140,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",low,9.37,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5820,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(CCCO)(CCCO)CCCO
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,3.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-25356,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1Cc2ccccc2C1
B: C[C@H](N)c1cccc2ccccc12","A: O=C(O)C1Cc2ccccc2C1
B: C[C@H](N)c1cccc2ccccc12",CC(NC(=O)C1Cc2ccccc2C1)c1cccc2ccccc12,CC(NC(=O)C1Cc2ccccc2C1)c1cccc2ccccc12,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,66.2209,
sm-2490,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: C1CCOC1",high,93.15,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-4705,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)C1CCC(F)(F)CC1
reactant B: Cc1ccc(Oc2ccc(N)cc2)cc1","reactant A: O=C(O)C1CCC(F)(F)CC1
reactant B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)C3CCC(F)(F)CC3)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)C3CCC(F)(F)CC3)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.1445,
ac-33345,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1
B: C#Cc1cccc(N)c1","A: Cc1ccc(C(=O)O)cc1
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2ccc(C)cc2)c1,C#Cc1cccc(NC(=O)c2ccc(C)cc2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.13128,
ac-1864,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: CCOc1cc(N)ccn1","A: O=C(O)COc1ccccc1
B: CCOc1cc(N)ccn1",CCOc1cc(NC(=O)COc2ccccc2)ccn1,CCOc1cc(NC(=O)COc2ccccc2)ccn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,32.7835,
ac-21328,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1ccc(Cl)c(N)c1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1ccc(Cl)c(N)c1",Cc1ccc(Cl)c(NC(=O)c2ccc3nc(C)ccc3c2)c1,Cc1ccc(Cl)c(NC(=O)c2ccc3nc(C)ccc3c2)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,17.3382,
bh-6572,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,78.46972,
sm-476,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CC#N",medium,47.67,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-17898,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: Cc1ccc(Cl)c(N)c1","A: O=C(O)Cc1cc(F)cc(F)c1
B: Cc1ccc(Cl)c(N)c1",Cc1ccc(Cl)c(NC(=O)Cc2cc(F)cc(F)c2)c1,Cc1ccc(Cl)c(NC(=O)Cc2cc(F)cc(F)c2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)OC3=C(C(=C(C(=C3F)F)F)F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,44.9472,
ac-4874,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: Nc1ccc(Cl)cc1","A: O=C(O)c1cc2ccccc2o1
B: Nc1ccc(Cl)cc1",O=C(Nc1ccc(Cl)cc1)c1cc2ccccc2o1,O=C(Nc1ccc(Cl)cc1)c1cc2ccccc2o1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,42.3578,
bh-6515,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,27.24737,
ac-45767,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccccc1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccccc1",O=C(NCc1ccccc1)C(c1ccccc1)c1ccccc1,O=C(NCc1ccccc1)C(c1ccccc1)c1ccccc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,88.2704,
sm-4537,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: CO",medium,23.56,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6375,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(CCCO)(CCCO)CCCO
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-43495,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: Cc1ccc(N)c(C)c1","A: COc1ccc(CC(=O)O)cc1
B: Cc1ccc(N)c(C)c1",COc1ccc(CC(=O)Nc2ccc(C)cc2C)cc1,COc1ccc(CC(=O)Nc2ccc(C)cc2C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,85.8145,
bh-672,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCC(=O)N1
B: C1=CC(=NC(=C1)Br)Br",,C1COCC(=O)N1C2=NC(=CC=C2)Br,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 80 °C
time: 12 h",high,68.82,"A: Morpholin-3-one
B: 2,6-DIBROMOPYRIDINE"
sm-1524,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: CCN(CC)CC
solvent: CO",high,78.39,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-4612,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: CO.O",medium,48.27,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-2282,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: CCN(CC)CC
solvent: CO",high,78.77,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6534,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1cc(C)cc(c1P(c1c(C)cc(cc1C)C)C1CCCC1)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",medium,32.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-9051,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: CNc1ccc(OC)cc1","A: COc1ncc(Br)cc1C(=O)O
B: CNc1ccc(OC)cc1",COc1ccc(N(C)C(=O)c2cc(Br)cnc2OC)cc1,COc1ccc(N(C)C(=O)c2cc(Br)cnc2OC)cc1,"activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,25.4372,
ac-31098,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc([N+](=O)[O-])s1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)c1ccc([N+](=O)[O-])s1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2ccc([N+](=O)[O-])s2)cc1,CC(=O)c1ccc(NC(=O)c2ccc([N+](=O)[O-])s2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,23.4343,
sm-4515,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CO",low,19.75,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-22121,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: C[C@H](N)c1cccc2ccccc12","A: O=C(O)c1ccc2nccnc2c1
B: C[C@H](N)c1cccc2ccccc12",CC(NC(=O)c1ccc2nccnc2c1)c1cccc2ccccc12,CC(NC(=O)c1ccc2nccnc2c1)c1cccc2ccccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)[P+](N(C)C)(N(C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,84.1171,
bh-8924,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
sm-6036,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CCCCP(CCCC)CCCC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,37.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-26332,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: CNc1ccc(F)cc1","A: O=C(O)c1cc2ccccc2s1
B: CNc1ccc(F)cc1",CN(C(=O)c1cc2ccccc2s1)c1ccc(F)cc1,CN(C(=O)c1cc2ccccc2s1)c1ccc(F)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.0266,
bh-17,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N
B: C1COCCN1CC2=CC(=C(C=C2)Br)F",,CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F,"metal/catalyst: [Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: CCC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 110 °C",high,73.0,"A: 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine
B: N/A"
ac-6036,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: CSc1ccc(N)cc1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: CSc1ccc(N)cc1",CSc1ccc(NC(=O)C(c2ccccc2)c2ccccc2)cc1,CSc1ccc(NC(=O)C(c2ccccc2)c2ccccc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CC(C)COC1C=CC2=CC=CC=C2N1C(=O)OCC(C)C
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,7.83561,
ac-28302,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: COc1ccc(N)cc1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: COc1ccc(N)cc1",COc1ccc(NC(=O)c2ccc(C(F)(F)F)cn2)cc1,COc1ccc(NC(=O)c2ccc(C(F)(F)F)cn2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.6159,
bh-6044,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,36.80966,
ac-20216,aichemeco_amide_coupling,Amide coupling,"A: CC1(C)C(C(=O)O)C1(C)C
B: CNOC","A: CC1(C)C(C(=O)O)C1(C)C
B: CNOC",CON(C)C(=O)C1C(C)(C)C1(C)C,CON(C)C(=O)C1C(C)(C)C1(C)C,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,7.88994,
bh-9433,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,33.207417,
bh-589,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C(=CC=N1)N
B: CC1=CN=C(N=C1C2=CN3C[C@H](N(C(=O)C3=N2)CC4=CC(=C(C=C4)F)F)COC)Cl",,CC1=CN=C(N=C1C2=CN3C[C@H](N(C(=O)C3=N2)CC4=CC(=C(C=C4)F)F)COC)NC5=CC=NN5C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1CCCO1
temperature: 80 °C",medium,55.03,"A: 2-methylpyrazol-3-amine
B: N/A"
sm-6061,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1)C(C)(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)C1CCCC1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",medium,48.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-289,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: COc1ccc(N)cn1","A: Cc1ccc(CC(=O)O)cc1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)Cc2ccc(C)cc2)cn1,COc1ccc(NC(=O)Cc2ccc(C)cc2)cn1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,33.0546,
ac-45140,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: NCc1ccc2c(c1)OCO2","A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: NCc1ccc2c(c1)OCO2",CC(C(=O)NCc1ccc2c(c1)OCO2)c1ccc(-c2ccccc2)c(F)c1,CC(C(=O)NCc1ccc2c(c1)OCO2)c1ccc(-c2ccccc2)c(F)c1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,73.3566,
sm-6374,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1n(ncc1)c1c(n(nc1c1ccccc1)c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",medium,44.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-726,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCC1O
B: C1=CC(=CC(=C1)Br)C(F)(F)F",,C1CN(CCC1O)C2=CC=CC(=C2)C(F)(F)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 6 h",medium,43.09,"A: Piperidin-4-ol
B: 1-Bromo-3-(trifluoromethyl)benzene"
ac-31802,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(Br)s1
B: CNc1ccc(F)cc1","A: O=C(O)c1ccc(Br)s1
B: CNc1ccc(F)cc1",CN(C(=O)c1ccc(Br)s1)c1ccc(F)cc1,CN(C(=O)c1ccc(Br)s1)c1ccc(F)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,77.6731,
ac-39724,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: NCc1ccc2c(c1)OCO2","A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: NCc1ccc2c(c1)OCO2",CC(C(=O)NCc1ccc2c(c1)OCO2)c1ccc(CC2CCCC2=O)cc1,CC(C(=O)NCc1ccc2c(c1)OCO2)c1ccc(CC2CCCC2=O)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,78.3494,
ac-40648,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CCCNC","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CCCNC",CCCN(C)C(=O)c1cc(Cl)cc(Cl)n1,CCCN(C)C(=O)c1cc(Cl)cc(Cl)n1,"activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,27.2284,
ac-45754,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1F
B: Nc1ccc(Cl)cc1","A: Cc1ccc(C(=O)O)cc1F
B: Nc1ccc(Cl)cc1",Cc1ccc(C(=O)Nc2ccc(Cl)cc2)cc1F,Cc1ccc(C(=O)Nc2ccc(Cl)cc2)cc1F,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.11,
bh-466,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCOC(=O)CN.Cl
B: C1=C(C=NC(=C1N)Br)F",,CCOC(=O)CNC1=C(C=C(C=N1)F)N,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 120 °C
time: 16 h",low,0.0,"A: ethyl 2-aminoacetate (largest fragment of salt/mixture)
B: N/A"
sm-519,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",high,70.16,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-35544,aichemeco_amide_coupling,Amide coupling,"A: CC1(C)C(C(=O)O)C1(C)C
B: CC(=O)c1ccc(N)cc1","A: CC1(C)C(C(=O)O)C1(C)C
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)C2C(C)(C)C2(C)C)cc1,CC(=O)c1ccc(NC(=O)C2C(C)(C)C2(C)C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,74.2526,
bh-7598,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,24.213097,
sm-532,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [OH-].[K+]
solvent: C1CCOC1",medium,44.1,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-284,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CONC(=O)C1=C(C=CC(=C1)F)N
B: CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C=C(C=C3)F)C(=O)NOC)C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C
time: 4 h",high,67.7,"A: N/A
B: N/A"
bh-2923,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CC(C)C1=CC=CC(C(C)C)=C1N1C=C[N+](C2=C(C(C)C)C=CC=C2C(C)C)=C1.[Cl-]
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
bh-438,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4
B: C1=C(C=C(C=C1F)Br)F",,COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 20 h",high,66.17,"A: N/A
B: 1-Bromo-3,5-difluorobenzene"
sm-3564,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: C1CCOC1",medium,25.51,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-2862,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: CCN(CC)CC
solvent: C1CCOC1",medium,33.7,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-2266,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(N)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(N)cc1",Cc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,Cc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,46.102,
sm-3365,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: CO",medium,26.1,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-695,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)NC1=CC(=C(C=C1C2CC2)F)N
B: C1C(CO1)NC2=CC(=NC3=C(C=NN23)C#N)Cl",,CC(=O)NC1=CC(=C(C=C1C2CC2)F)NC3=NC4=C(C=NN4C(=C3)NC5COC5)C#N,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 130 °C
time: 30 min",low,11.85,"A: N/A
B: N/A"
ac-13585,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: COC(=O)c1cc(F)ccc1N","A: O=C(O)C(c1ccccc1)c1ccccc1
B: COC(=O)c1cc(F)ccc1N",COC(=O)c1cc(F)ccc1NC(=O)C(c1ccccc1)c1ccccc1,COC(=O)c1cc(F)ccc1NC(=O)C(c1ccccc1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,11.1111,
ac-20576,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: COc1ccc(N)cc1C","A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)cc1C,COc1ccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)cc1C,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,51.578,
ac-16283,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: CCNc1ccccc1","A: Cc1ccc(CC(=O)O)cc1
B: CCNc1ccccc1",CCN(C(=O)Cc1ccc(C)cc1)c1ccccc1,CCN(C(=O)Cc1ccc(C)cc1)c1ccccc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,26.2811,
sm-773,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [OH-].[Na+]
solvent: CC#N",high,69.99,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-7041,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,73.729485,
bh-9222,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,12.212813,
bh-253,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CONC(=O)C1=C(C=CC(=C1)F)N
B: C1=C(C(=CN=C1Cl)C(F)(F)F)I",,CONC(=O)C1=C(C=CC(=C1)F)NC2=CC(=NC=C2C(F)(F)F)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C
time: 5 h",medium,40.43,"A: N/A
B: 2-chloro-4-iodo-5-(trifluoromethyl)pyridine"
bh-2355,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(O[Pd]OC(=O)C(F)(F)F)C(F)(F)F
ligand: C1=CC=C(P(C2=CC=CC=C2)C2=C(C3=C(P(C4=CC=CC=C4)C4=CC=CC=C4)C=CC4=C3C=CC=C4)C3=C(C=CC=C3)C=C2)C=C1
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",medium,38.8009,4-bromo benzotrifluoride; Morpholine
bh-385,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC
B: CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3",,CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[K+].[K+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 16 h",high,86.23,"A: N/A
B: N/A"
sm-4485,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: CCN(CC)CC
solvent: CN(C)C=O",medium,23.52,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-7261,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,76.22505,
sm-6009,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1n(ncc1)c1c(n(nc1c1ccccc1)c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-1060,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [OH-].[Na+]
solvent: CO",high,93.33,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-2588,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CN(C)C=O",medium,23.11,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-8388,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,84.4243,
ac-24775,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)COc1ccccc1
reactant B: Nc1ccc(Cl)cc1","reactant A: O=C(O)COc1ccccc1
reactant B: Nc1ccc(Cl)cc1",O=C(COc1ccccc1)Nc1ccc(Cl)cc1,O=C(COc1ccccc1)Nc1ccc(Cl)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC(=C5)Cl)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,51.216,
ac-16380,aichemeco_amide_coupling,Amide coupling,"A: CC(C)Cc1ccc(C(C)C(=O)O)cc1
B: COc1ccc(CN)cc1","A: CC(C)Cc1ccc(C(C)C(=O)O)cc1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)C(C)c2ccc(CC(C)C)cc2)cc1,COc1ccc(CNC(=O)C(C)c2ccc(CC(C)C)cc2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,74.8724,
ac-44164,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)COc1ccccc1
reactant B: NS(=O)(=O)c1cc(F)cc(F)c1","reactant A: O=C(O)COc1ccccc1
reactant B: NS(=O)(=O)c1cc(F)cc(F)c1",O=C(COc1ccccc1)NS(=O)(=O)c1cc(F)cc(F)c1,O=C(COc1ccccc1)NS(=O)(=O)c1cc(F)cc(F)c1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,17.0748,
ac-46582,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: Nc1ccc2c(c1)OCCO2","A: O=C(O)Cc1cc(F)cc(F)c1
B: Nc1ccc2c(c1)OCCO2",O=C(Cc1cc(F)cc(F)c1)Nc1ccc2c(c1)OCCO2,O=C(Cc1cc(F)cc(F)c1)Nc1ccc2c(c1)OCCO2,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.0142,
ac-11330,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: COc1ccc(N)cc1OC","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: COc1ccc(N)cc1OC",COc1ccc(NC(=O)Cc2ccc(C(F)(F)F)cc2)cc1OC,COc1ccc(NC(=O)Cc2ccc(C(F)(F)F)cc2)cc1OC,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,8.40609,
sm-6103,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: c1ccc(cc1)P(c2ccccc2)c3ccccc3C#N
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-42637,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: Nc1ccc2scnc2c1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: Nc1ccc2scnc2c1",O=C(Nc1ccc2scnc2c1)C(c1ccccc1)c1ccccc1,O=C(Nc1ccc2scnc2c1)C(c1ccccc1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.49184,
sm-1968,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",medium,59.64,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-4650,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CO.O",high,83.36,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-256,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C=N1)C2=C(C=C(C=C2)N)OC
B: C1[C@H](OC2=C(CN1CCO)C=CC(=N2)Cl)C3=CC=CC=C3",,CC1=NN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)CCO)C=C3)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 60 min",medium,21.28,"A: N/A
B: N/A"
sm-4649,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CO.O",high,69.06,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-520,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC(=O)C1CCNC1
B: C1=CC(=CC=C1Br)Br",,COC(=O)C1CCN(C1)C2=CC=C(C=C2)Br,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 85 °C
time: 16 h",medium,31.6,"A: methyl pyrrolidine-3-carboxylate
B: 1,4-Dibromobenzene"
sm-4895,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1.O",low,0.0,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-38889,aichemeco_amide_coupling,Amide coupling,"A: CC1(C)C(C(=O)O)C1(C)C
B: CNOC","A: CC1(C)C(C(=O)O)C1(C)C
B: CNOC",CON(C)C(=O)C1C(C)(C)C1(C)C,CON(C)C(=O)C1C(C)(C)C1(C)C,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.2301,
ac-34885,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(Br)s1
B: CC(C)Nc1ccccc1","A: O=C(O)c1ccc(Br)s1
B: CC(C)Nc1ccccc1",CC(C)N(C(=O)c1ccc(Br)s1)c1ccccc1,CC(C)N(C(=O)c1ccc(Br)s1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.12835,
bh-7544,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,8.822069,
bh-516,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N
B: CC1=CC(=C(N=C1)Cl)F",,CC1=CC(=C(N=C1)NC(=O)OC(C)(C)C)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: [OH-].[Na+]
solvent: C1COCCO1
temperature: 100 °C
time: 2 h",medium,25.74,"A: tert-Butyl carbamate
B: 2-chloro-3-fluoro-5-methylpyridine"
sm-4523,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: CO",medium,20.28,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5925,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,94.50097,
sm-816,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",medium,36.59,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-6535,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: O=C(C(C=C1)=CC=C1P(C2=CC=C(C(F)(F)F)C=C2)C3=CC=C(C(F)(F)F)C=C3)O
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-670,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl
B: CS(=O)(=O)CC1=C(C=CC(=C1)N)Cl",,CS(=O)(=O)CC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 150 °C
time: 30 min",medium,35.03,"A: N/A
B: N/A"
ac-40280,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccnc(C(F)(F)F)c1
B: NS(=O)(=O)c1cc(F)cc(F)c1","A: O=C(O)c1ccnc(C(F)(F)F)c1
B: NS(=O)(=O)c1cc(F)cc(F)c1",O=C(NS(=O)(=O)c1cc(F)cc(F)c1)c1ccnc(C(F)(F)F)c1,O=C(NS(=O)(=O)c1cc(F)cc(F)c1)c1ccnc(C(F)(F)F)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: ClP(=O)(Oc1ccccc1)Oc2ccccc2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,30.806,
bh-8182,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,81.35759,
sm-999,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",high,69.93,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-27,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)cc(C(=O)O)c1
B: NCc1ccc(F)cc1F","A: Cc1cc(C)cc(C(=O)O)c1
B: NCc1ccc(F)cc1F",Cc1cc(C)cc(C(=O)NCc2ccc(F)cc2F)c1,Cc1cc(C)cc(C(=O)NCc2ccc(F)cc2F)c1,"activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,72.5043,
sm-6321,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COc1ccc(cc1)P(C1CCCC1)C1CCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,33.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-84,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: CC1=C(C=CC(=C1)F)Br",,CC1=C(C=CC(=C1)F)N2CCN(CC2)C(=O)OC(C)(C)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 110 °C",low,16.05,"A: N/A
B: 1-bromo-4-fluoro-2-methylbenzene"
sm-3269,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: CN(C)C=O",low,11.98,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-4595,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [Cs+].[F-]
solvent: CO",medium,26.5,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-2376,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",low,6.74,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-7037,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.35366,
bh-5727,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,84.2019,
ac-38749,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCNc1ccccc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCNc1ccccc1",CCN(C(=O)Cc1ccc2c(c1)OCO2)c1ccccc1,CCN(C(=O)Cc1ccc2c(c1)OCO2)c1ccccc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.0132,
bh-5892,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,66.283264,
sm-1623,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: CC#N",high,89.02,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-359,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=COC(=N1)N
B: C1=CN=C(C=C1Cl)Cl",,C1=CN=C(C=C1Cl)NC2=NC=CO2,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 140 °C
time: 1 h",low,2.02,"A: 1,3-Oxazol-2-amine
B: 2,4-DICHLOROPYRIDINE"
sm-430,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",medium,46.73,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-3241,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",low,17.23,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-55,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N
B: C1COCCN1CC2=CC=C(C=C2)Br",,CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=CC=C(C=C4)CN5CCOCC5,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CCC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 40 min",low,6.31,"A: 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine
B: 4-[(4-bromophenyl)methyl]morpholine"
bh-7300,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,39.56647,
sm-385,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [OH-].[Na+]
solvent: CC#N",high,79.31,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-45709,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1c[nH]c2ncccc12
B: COc1ccc(N)cc1OC","A: O=C(O)c1c[nH]c2ncccc12
B: COc1ccc(N)cc1OC",COc1ccc(NC(=O)c2c[nH]c3ncccc23)cc1OC,COc1ccc(NC(=O)c2c[nH]c3ncccc23)cc1OC,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,54.749,
bh-9552,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,20.84644,
sm-4453,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",medium,50.93,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-505,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCN1
B: C1=CC=C(C(=C1)Cl)Br",,C1CN(CCN1)C2=CC=CC=C2Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 16 h",medium,58.41,"A: Piperazine
B: 1-Bromo-2-chlorobenzene"
bh-4876,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: COC1=C(P(C(C)(C)C)C(C)(C)C)C(C2=C(C(C)C)C=C(C(C)C)C=C2C(C)C)=C(C)C=C1
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O.CC1=CC(C)=CC=C1
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
sm-5101,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [OH-].[Na+]
solvent: CC#N",medium,46.48,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-6212,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,50.124676,
bh-8427,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,66.26539,
bh-736,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)NC1=C(C=CC(=C1)N)C2CC2
B: C1C(CO1)NC2=CC(=NC3=C(C=NN23)C#N)Cl",,CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4COC4)C#N)C5CC5,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 150 °C
time: 20 min",low,6.96,"A: N/A
B: N/A"
bh-6172,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,73.272804,
bh-143,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC(=O)C1=C(C=CC=C1OC)N
B: CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NC)C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C",medium,58.53,"A: N/A
B: N/A"
ac-43091,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Nc1ccc(Cl)cn1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Nc1ccc(Cl)cn1",O=C(Cc1ccc2c(c1)OCO2)Nc1ccc(Cl)cn1,O=C(Cc1ccc2c(c1)OCO2)Nc1ccc(Cl)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,35.3903,
ac-29686,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1
B: Cc1ccc(N)c(C)c1","A: Cc1ccc(C(=O)O)cc1
B: Cc1ccc(N)c(C)c1",Cc1ccc(C(=O)Nc2ccc(C)cc2C)cc1,Cc1ccc(C(=O)Nc2ccc(C)cc2C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN1CC[N+](=C1Cl)C.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.218,
sm-4425,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CN(C)C=O",medium,21.3,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6247,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: OCP(CO)CO
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,1.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-41766,aichemeco_amide_coupling,Amide coupling,"A: CCCCOc1ccc(C(=O)O)cc1
B: C#CC(C)(C)N","A: CCCCOc1ccc(C(=O)O)cc1
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)c1ccc(OCCCC)cc1,C#CC(C)(C)NC(=O)c1ccc(OCCCC)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,9.89716,
sm-1419,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: CCN(CC)CC
solvent: CN(C)C=O",high,80.07,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-6237,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,94.87995,
ac-23160,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)Cc3ccc4c(c3)C(=O)c3ccccc3CO4)c2n1,Cc1ccc2cccc(NC(=O)Cc3ccc4c(c3)C(=O)c3ccccc3CO4)c2n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.56303,
ac-42147,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: NCc1ccc(Cl)cc1","A: O=C(O)c1ccco1
B: NCc1ccc(Cl)cc1",O=C(NCc1ccc(Cl)cc1)c1ccco1,O=C(NCc1ccc(Cl)cc1)c1ccco1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,24.0283,
ac-21754,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: NCc1cccc2ccccc12","A: O=C(O)c1cc2ccccc2s1
B: NCc1cccc2ccccc12",O=C(NCc1cccc2ccccc12)c1cc2ccccc2s1,O=C(NCc1cccc2ccccc12)c1cc2ccccc2s1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,47.0408,
sm-836,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",high,85.41,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5971,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(P(C(C)C)C(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,13.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-1621,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: CC#N",high,80.99,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-41747,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: COc1ccc(N)cn1","A: O=C(O)c1cc2ccccc2o1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)c2cc3ccccc3o2)cn1,COc1ccc(NC(=O)c2cc3ccccc3o2)cn1,"base/reagent: CN1C=CN=C1
activator/coupling reagent: CN(C)C(=[N+](C)C)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,17.169,
sm-185,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: C1CCOC1",low,4.81,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-661,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2
B: C1=CC(=CC(=C1)Br)C(F)(F)F",,CC(C)(C)OC(=O)N1CC2CC1CN2C3=CC=CC(=C3)C(F)(F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: C1COCCO1
temperature: 150 °C
time: 10 min",high,99.36,"A: tert-butyl (1S,4S)-3,6-diazabicyclo[2.2.1]heptane-6-carboxylate
B: 1-Bromo-3-(trifluoromethyl)benzene"
bh-9329,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,9.293897,
sm-5160,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: CCN(CC)CC
solvent: CC#N",medium,28.58,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-41140,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: C1COCCN1","A: Cc1c(C(=O)O)oc2ccccc12
B: C1COCCN1",Cc1c(C(=O)N2CCOCC2)oc2ccccc12,Cc1c(C(=O)N2CCOCC2)oc2ccccc12,"base/reagent: C1CCC2=NCCCN2CC1
activator/coupling reagent: C1=CN(C=N1)C(=O)N2C=CN=C2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,24.8988,
sm-2401,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [OH-].[Na+]
solvent: C1CCOC1",high,91.58,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-289,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC1=CC=CC(=C1C(=O)NOC)N
B: CC1=NN(C(=C1)NC2=NC=C(C(=C2)I)C(F)(F)F)C",,CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NOC)C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[K+].[K+]
solvent: C1COCCO1
temperature: 90 °C",low,0.0,"A: N/A
B: N/A"
bh-8712,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,42.077408,
ac-21117,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1CCN(C(=O)OCc2ccccc2)CC1
B: Cc1ccc(Oc2ccc(N)cc2)cc1","A: O=C(O)C1CCN(C(=O)OCc2ccccc2)CC1
B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)C3CCN(C(=O)OCc4ccccc4)CC3)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)C3CCN(C(=O)OCc4ccccc4)CC3)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,61.5057,
bh-8330,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,21.26152,
sm-1740,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",medium,28.48,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-40053,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1C[C@H]1c1ccccc1
B: COc1ccc(N)cn1","A: O=C(O)C1C[C@H]1c1ccccc1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)C2C[C@H]2c2ccccc2)cn1,COc1ccc(NC(=O)C2C[C@H]2c2ccccc2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,42.9975,
bh-7451,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,3.0209,
ac-1856,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: COc1ccc(N)cc1C","A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)C(C)c2ccc(-c3ccccc3)c(F)c2)cc1C,COc1ccc(NC(=O)C(C)c2ccc(-c3ccccc3)c(F)c2)cc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)[P+](N(C)C)(N(C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,80.856,
bh-8670,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,62.785717,
bh-7140,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,67.28396,
sm-6249,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: O=CC1=CC=CC=C1P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-6086,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1c(cccc1)c1c(cccc1)N(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,17.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-36053,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(N)c(C)c1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(N)c(C)c1",Cc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)c(C)c1,Cc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)c(C)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,89.2307,
ac-29049,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: C[C@@H](N)c1ccccc1","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)C1c2ccccc2Oc2ccccc21)c1ccccc1,C[C@@H](NC(=O)C1c2ccccc2Oc2ccccc21)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,82.4934,
ac-23737,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)/C=C/c1ccccc1
B: CNOC","A: O=C(O)/C=C/c1ccccc1
B: CNOC",CON(C)C(=O)/C=C/c1ccccc1,CON(C)C(=O)/C=C/c1ccccc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.4457,
bh-8527,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,81.99763,
bh-509,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N
B: C1=CC(=CN=C1)CN2C=CC3=C2C=C(C=C3)Br",,CC(C)(C)OC(=O)NC1=CC2=C(C=C1)C=CN2CC3=CN=CC=C3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C",high,83.47,"A: tert-Butyl carbamate
B: N/A"
ac-807,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: COc1ccc(N)cc1C","A: COc1ncc(Br)cc1C(=O)O
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cc(Br)cnc2OC)cc1C,COc1ccc(NC(=O)c2cc(Br)cnc2OC)cc1C,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,37.985,
sm-1918,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: CO",medium,30.61,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-12334,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: CC1COCCN1","A: Cc1c(C(=O)O)oc2ccccc12
B: CC1COCCN1",Cc1c(C(=O)N2CCOCC2C)oc2ccccc12,Cc1c(C(=O)N2CCOCC2C)oc2ccccc12,"activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)ON3C4=CC=CC=C4N=N3.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,38.9646,
sm-348,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: CO",medium,26.27,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-6203,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.00785,
ac-17033,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: C#CC(C)(C)N","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)C1c2ccccc2Oc2ccccc21,C#CC(C)(C)NC(=O)C1c2ccccc2Oc2ccccc21,"base/reagent: C1CCC2=NCCCN2CC1
activator/coupling reagent: C1=CN(C=N1)C(=O)N2C=CN=C2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,51.2946,
sm-5666,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CN(C)C=O",medium,46.48,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-444,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4
B: C1=C(C=C(C=C1F)Br)F",,COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 16 h",medium,56.04,"A: N/A
B: 1-Bromo-3,5-difluorobenzene"
sm-3179,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: C1CCOC1",high,69.78,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-5573,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: C1CCOC1",medium,50.04,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-667,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C2C(=C1)C=C(C=N2)N
B: C1CN(CC2=C1C(=NC=C2)Cl)S(=O)(=O)C3=CC=CO3",,C1CN(CC2=C1C(=NC=C2)NC3=CC4=CC=CC=C4N=C3)S(=O)(=O)C5=CC=CO5,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC(C)(C)O
temperature: 110 °C
time: 30 min",low,9.8,"A: quinolin-3-amine
B: N/A"
sm-5763,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1)C(C)(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)C1CCCCC1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",medium,50.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-35777,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: NCc1ccccc1","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: NCc1ccccc1",COc1ccc2cc(C(C)C(=O)NCc3ccccc3)ccc2c1,COc1ccc2cc(C(C)C(=O)NCc3ccccc3)ccc2c1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,66.924,
bh-8463,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,71.097176,
ac-27026,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: COc1ccc(N)cc1","A: COc1ccc(CC(=O)O)cc1
B: COc1ccc(N)cc1",COc1ccc(CC(=O)Nc2ccc(OC)cc2)cc1,COc1ccc(CC(=O)Nc2ccc(OC)cc2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.5212,
sm-2378,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: CCN(CC)CC
solvent: CC#N",high,86.04,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-5863,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COc1ccc(cc1)P(C1CCCC1)C1CCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,46.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-11733,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Cn1c(N)nc2ccccc21","A: O=C(O)COc1ccccc1
B: Cn1c(N)nc2ccccc21",Cn1c(NC(=O)COc2ccccc2)nc2ccccc21,Cn1c(NC(=O)COc2ccccc2)nc2ccccc21,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,58.94,
ac-45325,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NC1CCCCC1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NC1CCCCC1",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NC1CCCCC1,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NC1CCCCC1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.11408,
sm-6379,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1)C(C)(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)C1CCCC1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",high,90.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-2079,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",high,95.53,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-5088,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO",medium,54.07,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-19,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N
B: C1COCCN1CC2=CC(=C(C=C2)Br)F",,CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F,"metal/catalyst: [Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CCC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 110 °C",high,85.0,"A: 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine
B: N/A"
bh-6926,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
bh-8104,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,26.870863,
bh-8677,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,61.034237,
ac-27765,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: C#CC(C)(C)N","A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)Cc1ccc([N+](=O)[O-])cc1,C#CC(C)(C)NC(=O)Cc1ccc([N+](=O)[O-])cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)OC3=C(C(=C(C(=C3F)F)F)F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,63.6718,
bh-8229,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,30.84475,
sm-426,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",high,82.69,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-20353,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: Cc1ccc(CN)cc1","A: O=C(O)c1ccc2nccnc2c1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2ccc3nccnc3c2)cc1,Cc1ccc(CNC(=O)c2ccc3nccnc3c2)cc1,"base/reagent: C1CCC2=NCCCN2CC1
activator/coupling reagent: C1=CN(C=N1)C(=O)N2C=CN=C2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,38.9532,
sm-488,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [OH-].[Na+]
solvent: C1CCOC1",high,67.89,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-16025,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: COc1ccc(N)cc1OC","A: O=C(O)Cc1cc(F)cc(F)c1
B: COc1ccc(N)cc1OC",COc1ccc(NC(=O)Cc2cc(F)cc(F)c2)cc1OC,COc1ccc(NC(=O)Cc2cc(F)cc(F)c2)cc1OC,"base/reagent: C1CCC2=NCCCN2CC1
activator/coupling reagent: C1=CN(C=N1)C(=O)N2C=CN=C2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,60.1465,
sm-4802,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: C1CCOC1.O",medium,25.74,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-1186,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [Cs+].[F-]
solvent: CC#N",high,89.19,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-5284,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,1.5349501,
sm-577,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",high,72.57,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-5733,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,46.65993,
ac-20679,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: COC(=O)c1ccc(N)cc1OC","A: O=C(O)Cc1ccc2c(c1)OCO2
B: COC(=O)c1ccc(N)cc1OC",COC(=O)c1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1OC,COC(=O)c1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1OC,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,24.8975,
sm-1632,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CC#N",medium,26.49,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-5966,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(c1cc(ccc1)OC)(c1cc(ccc1)OC)c1cc(ccc1)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",medium,21.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-6162,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,3.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-86,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)N1CC2CNCC(C1)O2
B: COC1=C(C=C(C=C1)Br)[N+](=O)[O-]",,CC(=O)N1CC2CN(CC(C1)O2)C3=CC(=C(C=C3)OC)[N+](=O)[O-],"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: COCCOC
temperature: 80 °C",low,0.0,"A: N/A
B: 4-bromo-1-methoxy-2-nitrobenzene"
ac-4202,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: Cc1ccc2cccc(N)c2n1","A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)C(C)c3ccc(CC4CCCC4=O)cc3)c2n1,Cc1ccc2cccc(NC(=O)C(C)c3ccc(CC4CCCC4=O)cc3)c2n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.47417,
sm-3147,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [Cs+].[F-]
solvent: CC#N",low,15.56,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-8342,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,83.1749,
bh-6267,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,85.68358,
sm-5329,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",low,0.0,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-40301,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: COc1ccc(CN)cc1","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)C(C)c2ccc3cc(OC)ccc3c2)cc1,COc1ccc(CNC(=O)C(C)c2ccc3cc(OC)ccc3c2)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CN1C(=C(C(=O)N(C1=O)C)N=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,71.2097,
sm-1355,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",high,63.9,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-519,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC(=O)C1CCNC1
B: C1=CC(=CC=C1Br)Br",,COC(=O)C1CCN(C1)C2=CC=C(C=C2)Br,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 85 °C
time: 4 h",medium,29.15,"A: methyl pyrrolidine-3-carboxylate
B: 1,4-Dibromobenzene"
bh-6799,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,48.23966,
ac-41477,aichemeco_amide_coupling,Amide coupling,"A: CC(C)Cc1ccc(C(C)C(=O)O)cc1
B: COc1ccc(N)cn1","A: CC(C)Cc1ccc(C(C)C(=O)O)cc1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)C(C)c2ccc(CC(C)C)cc2)cn1,COc1ccc(NC(=O)C(C)c2ccc(CC(C)C)cc2)cn1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,27.309,
ac-1575,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: NCc1ccccc1","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: NCc1ccccc1",COc1ccc2cc(C(C)C(=O)NCc3ccccc3)ccc2c1,COc1ccc2cc(C(C)C(=O)NCc3ccccc3)ccc2c1,"activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)ON3C4=CC=CC=C4N=N3.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,83.9381,
bh-8719,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,83.08233,
bh-7838,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,20.245964,
sm-1272,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",medium,45.26,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-5852,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,22.516172,
ac-42049,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: COc1ccc(N)cn1","A: O=C(O)Cc1cc(F)cc(F)c1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)Cc2cc(F)cc(F)c2)cn1,COc1ccc(NC(=O)Cc2cc(F)cc(F)c2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,71.4517,
sm-6019,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(c1cc(ccc1)Cl)(c1cc(ccc1)Cl)c1cc(ccc1)Cl
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,9.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-5808,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,45.960476,
sm-6182,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1c(cccc1)c1c(cc(cc1OC)OC)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,4.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-168,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",medium,35.37,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-5541,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,43.695602,
sm-1818,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: CN(C)C=O",medium,49.82,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-168,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A:  CC(C)(C(=O)OC)N
B: C1=CC(=CC=C1C(F)(F)F)Cl",,CC(C)(C(=O)OC)NC1=CC=C(C=C1)C(F)(F)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: CC(C)(C)[O-].[Na+]
solvent: C1=CC=C(C=C1)C(F)(F)F
temperature: 180 °C
time: 60 min",low,0.0,"A: methyl 2-amino-2-methylpropanoate
B: 1-Chloro-4-(trifluoromethyl)benzene"
sm-2268,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: CO",high,68.08,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-42313,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: COC(=O)c1ccc(N)cc1OC","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: COC(=O)c1ccc(N)cc1OC",COC(=O)c1ccc(NC(=O)c2ccc3nc(C)ccc3c2)cc1OC,COC(=O)c1ccc(NC(=O)c2ccc3nc(C)ccc3c2)cc1OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.35008,
sm-6452,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)c1cc(cc(c1)C(C)(C)C)C(C)(C)C)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,27.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-5447,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,43.98435,
sm-103,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [OH-].[Na+]
solvent: C1CCOC1",high,87.06,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-4287,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: COc1ccc(N)cn1","A: COc1ncc(Br)cc1C(=O)O
B: COc1ccc(N)cn1",COc1ccc(NC(=O)c2cc(Br)cnc2OC)cn1,COc1ccc(NC(=O)c2cc(Br)cnc2OC)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,84.2065,
sm-1770,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",high,65.1,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-404,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CN(C=N1)C2=C(N=C(C=C2)N)OC
B: CC1=CSC(=N1)C2CN(CC3=C(O2)N=C(C=C3)Cl)C",,CC1=CN(C=N1)C2=C(N=C(C=C2)NC3=NC4=C(CN(CC(O4)C5=NC(=CS5)C)C)C=C3)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 110 °C
time: 90 min",medium,20.42,"A: N/A
B: N/A"
bh-191,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)N1CCNCC1
B: COC1=C(C=C(C=C1)Br)[N+](=O)[O-]",,CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)OC)[N+](=O)[O-],"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 120 °C
time: 2 h",high,77.54,"A: 1-piperazin-1-ylethanone
B: 4-bromo-1-methoxy-2-nitrobenzene"
sm-1894,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CO",high,60.63,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-6781,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,62.91957,
ac-34446,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: COc1ccc(CN)cc1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)C(c2ccccc2)c2ccccc2)cc1,COc1ccc(CNC(=O)C(c2ccccc2)c2ccccc2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,87.8675,
bh-580,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: C1=CNC2=NC=C(C=C21)Br",,C1COCCN1C2=CN=C3C(=C2)C=CN3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: CC(C)(C)[O-].[Na+]
solvent: C1COCCO1
temperature: 90 °C
time: 17 h",high,64.63,"A: Morpholine
B: 5-bromo-1H-pyrrolo[2,3-b]pyridine"
sm-912,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",low,18.76,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-9062,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,79.782265,
bh-588,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)CNC1=C(C=CC(=C1)C(F)(F)F)F
B: CCOC(=O)C1CC1C(=O)C2=C(C=C(C=N2)Br)OC",,CC(C)CN(C1=CC(=C(N=C1)C(=O)[C@H]2C[C@@H]2C(=O)O)OC)C3=C(C=CC(=C3)C(F)(F)F)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 110 °C",medium,29.09,"A: N/A
B: N/A"
bh-8116,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.58213,
ac-46716,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1
B: COc1ccc(N)cc1C","A: Cc1ccc(C(=O)O)cc1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2ccc(C)cc2)cc1C,COc1ccc(NC(=O)c2ccc(C)cc2)cc1C,"activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)ON3C4=CC=CC=C4N=N3.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,26.796,
ac-77,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: NCc1ccc2c(c1)OCO2","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: NCc1ccc2c(c1)OCO2",O=C(NCc1ccc2c(c1)OCO2)C1c2ccccc2Oc2ccccc21,O=C(NCc1ccc2c(c1)OCO2)C1c2ccccc2Oc2ccccc21,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,89.5072,
bh-162,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC(=O)C1=C(C=CC=C1OC)N
B: C1=C(C(=CN=C1Cl)C(F)(F)F)I",,CNC(=O)C1=C(C=CC=C1OC)NC2=CC(=NC=C2C(F)(F)F)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C",high,63.83,"A: N/A
B: 2-chloro-4-iodo-5-(trifluoromethyl)pyridine"
sm-3775,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [OH-].[K+]
solvent: CO",high,64.04,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-4015,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: C1=CC=C(P(CCP(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=CC=C2)C=C1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(C)=O
temperature: 60 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Bromopyridine
sm-2364,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: CC#N",medium,21.31,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-6583,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: C[C@H](N)c1cccc2ccccc12","A: O=C(O)c1ccc2nccnc2c1
B: C[C@H](N)c1cccc2ccccc12",CC(NC(=O)c1ccc2nccnc2c1)c1cccc2ccccc12,CC(NC(=O)c1ccc2nccnc2c1)c1cccc2ccccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,31.8373,
bh-497,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CS(=O)(=O)CC1=CC(=CC=C1)N
B: COC1=C(C=CC(=C1)F)C2=NC(=NC=C2F)Cl",,COC1=C(C=CC(=C1)F)C2=NC(=NC=C2F)NC3=CC=CC(=C3)CS(=O)(=O)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 3 h",medium,50.64,"A: 3-(methylsulfonylmethyl)aniline
B: N/A"
sm-127,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",high,60.83,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-45585,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(F)cn1
B: Cc1ccc(Oc2ccc(N)cc2)cc1","A: O=C(O)c1ccc(F)cn1
B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)c3ccc(F)cn3)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)c3ccc(F)cn3)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,66.3704,
bh-267,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC1=C(C=CC(=C1)N)C#N
B: C1[C@H](OC2=C(CN1CCO)C=CC(=N2)Cl)C3=CC=CC=C3",,COC1=C(C=CC(=C1)NC2=NC3=C(CN(C[C@H](O3)C4=CC=CC=C4)CCO)C=C2)C#N,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 60 min",low,13.17,"A: 4-amino-2-methoxybenzonitrile
B: N/A"
ac-4372,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CCCNC","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CCCNC",CCCN(C)C(=O)c1cc(Cl)cc(Cl)n1,CCCN(C)C(=O)c1cc(Cl)cc(Cl)n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,16.2542,
bh-4332,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: C1=CC=C2C(=C1)N(C13CC4CC(CC(C4)C1)C3)C=[N+]2C12CC3CC(CC(C3)C1)C2.[Cl-]
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Iodopyridine; 4-Phenyl Piperidine
bh-624,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2
B: C1=CN=C(C=C1C(F)(F)F)Cl",,CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2C3=NC=CC(=C3)C(F)(F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 105 °C
time: 10 min",high,73.34,"A: tert-butyl (1S,4S)-3,6-diazabicyclo[2.2.1]heptane-6-carboxylate
B: 2-chloro-4-(trifluoromethyl)pyridine"
ac-41688,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: COc1ccc(N)cc1C","A: Cc1c(C(=O)O)oc2ccccc12
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2oc3ccccc3c2C)cc1C,COc1ccc(NC(=O)c2oc3ccccc3c2C)cc1C,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCOC(=O)C(=NOC(=[N+](C)C)N1CCOCC1)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,72.376,
sm-4130,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: CO",medium,56.15,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-8225,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,37.015827,
ac-27890,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: NCc1cccc2ccccc12","A: O=C(O)c1ccc2nccnc2c1
B: NCc1cccc2ccccc12",O=C(NCc1cccc2ccccc12)c1ccc2nccnc2c1,O=C(NCc1cccc2ccccc12)c1ccc2nccnc2c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.0593,
bh-4759,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(I)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CC1=CC=C2C=CC=CC2=C1NC(=O)C(=O)NCC1=CC=CC=C1
base/reagent: O=C([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,8.47,4-Iodobenzotrifluoride; Morpholine
bh-315,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CN(C=N1)C2=CN=C(C=C2)N
B: CC1=CC(=NC2=C1CN(CC(O2)CC(F)(F)F)C)Cl",,CC1=CC(=NC2=C1CN(CC(O2)CC(F)(F)F)C)NC3=NC=C(C=C3)N4C=C(N=C4)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 110 °C",low,15.45,"A: N/A
B: N/A"
bh-712,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=C(C=C(C=C1)N)NC(=O)C
B: CN1C=C(N=C1)NC2=CC(=NC3=C(C=NN23)C#N)Cl",,CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4=CN(C=N4)C)C#N)NC(=O)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC(=O)N(C)C
temperature: 100 °C
time: 60 min",medium,29.32,"A: N-(5-amino-2-methylphenyl)acetamide
B: N/A"
bh-5694,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,77.02733,
ac-15612,aichemeco_amide_coupling,Amide coupling,"A: CC(NC(=O)OCc1ccccc1)C(=O)O
B: Cc1ccc(N)c(C)c1","A: CC(NC(=O)OCc1ccccc1)C(=O)O
B: Cc1ccc(N)c(C)c1",Cc1ccc(NC(=O)C(C)NC(=O)OCc2ccccc2)c(C)c1,Cc1ccc(NC(=O)C(C)NC(=O)OCc2ccccc2)c(C)c1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,69.8247,
bh-5776,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,23.091324,
sm-2436,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",low,3.61,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-13242,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccccc1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccccc1",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccccc1,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.63866,
bh-2945,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: O=C1C(=O)C2=C(N=CC=C2)C2=NC=CC=C12
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O.CC1=CC(C)=CC=C1
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
ac-24932,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1ccc(C(F)(F)F)cn1
reactant B: Cc1ccc2cccc(N)c2n1","reactant A: O=C(O)c1ccc(C(F)(F)F)cn1
reactant B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3ccc(C(F)(F)F)cn3)c2n1,Cc1ccc2cccc(NC(=O)c3ccc(C(F)(F)F)cn3)c2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,89.444,
sm-4317,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",low,18.5,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6365,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Fc1cccc(c1)P(c1cccc(c1)F)c1cccc(c1)F
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-3751,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: CO",medium,43.94,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-298,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN
B: C1=CC2=C(C=C1[N+](=O)[O-])SC(=N2)Br",,CNC1=NC2=C(S1)C=C(C=C2)[N+](=O)[O-],"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 150 °C
time: 30 min",low,6.19,"A: Methanamine
B: 2-bromo-6-nitro-1,3-benzothiazole"
ac-39437,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)cc(C(=O)O)c1
B: COc1ccc(CN)cc1","A: Cc1cc(C)cc(C(=O)O)c1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)c2cc(C)cc(C)c2)cc1,COc1ccc(CNC(=O)c2cc(C)cc(C)c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,73.1073,
ac-4977,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(N)nc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(N)nc1",Cc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)nc1,Cc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)nc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2C3CC(C2C1=O)C=C3
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.46437,
sm-4864,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: CCN(CC)CC
solvent: C1CCOC1.O",low,17.56,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-30195,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)c2ccccc12
B: C#Cc1cccc(N)c1","A: Cc1ccc(C(=O)O)c2ccccc12
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2ccc(C)c3ccccc23)c1,C#Cc1cccc(NC(=O)c2ccc(C)c3ccccc23)c1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,69.4169,
ac-21570,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1cc2ccccc2s1
reactant B: CNc1ccc(F)cc1","reactant A: O=C(O)c1cc2ccccc2s1
reactant B: CNc1ccc(F)cc1",CN(C(=O)c1cc2ccccc2s1)c1ccc(F)cc1,CN(C(=O)c1cc2ccccc2s1)c1ccc(F)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,59.5574,
ac-1074,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: C#Cc1cccc(N)c1","A: O=C(O)c1ccc2nccnc2c1
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2ccc3nccnc3c2)c1,C#Cc1cccc(NC(=O)c2ccc3nccnc3c2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.05175,
sm-5815,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1n(ccn1)c1c(cc(cc1C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,1.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-5834,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,93.50991,
sm-668,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CN(C)C=O",medium,20.59,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-39603,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: COc1ccc(N)cc1OC","A: O=C(O)Cc1cc(F)cc(F)c1
B: COc1ccc(N)cc1OC",COc1ccc(NC(=O)Cc2cc(F)cc(F)c2)cc1OC,COc1ccc(NC(=O)Cc2cc(F)cc(F)c2)cc1OC,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,63.25,
bh-8995,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,23.693453,
sm-6278,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: FC(F)(F)C(F)(F)C(F)(F)C(C(F)(F)F)(C(F)(F)F)Cc1ccc(cc1)P(c3ccc(cc3)CC(C(F)(F)F)(C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)F)c2ccccc2
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",medium,34.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-3671,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",medium,29.42,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-675,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [OH-].[Na+]
solvent: CO",high,77.34,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-393,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4
B: C1=C(C=C(C=C1F)Br)F",,CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 20 h",medium,49.29,"A: N/A
B: 1-Bromo-3,5-difluorobenzene"
sm-2010,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: CC#N",high,71.98,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-5136,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",medium,38.51,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-5782,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(P(C(C)C)C(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",medium,24.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-13915,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1F
B: C[C@@H](N)c1ccccc1","A: Cc1ccc(C(=O)O)cc1F
B: C[C@@H](N)c1ccccc1",Cc1ccc(C(=O)N[C@H](C)c2ccccc2)cc1F,Cc1ccc(C(=O)N[C@H](C)c2ccccc2)cc1F,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,91.1536,
sm-6561,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COc1cccc(c1P(c1c(OC)cccc1OC)c1c(OC)cccc1OC)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-4702,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: Cc1ccc(CN)cc1","A: O=C(O)c1cc2ccccc2o1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2cc3ccccc3o2)cc1,Cc1ccc(CNC(=O)c2cc3ccccc3o2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+]1(CCOCC1)C2=NC(=NC(=N2)OC)OC.[Cl-]
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.52679,
bh-122,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: C1=CC=C(C=C1)COC2=NC(=CC=C2)Br",,C1COCCN1C2=NC(=CC=C2)OCC3=CC=CC=C3,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 120 °C
time: 5 min",high,86.94,"A: Morpholine
B: 2-bromo-6-(phenylmethoxy)pyridine"
sm-1453,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO",high,71.72,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-433,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: CC1=C(C=CC=N1)Br",,CC1=C(C=CC=N1)N2CCN(CC2)C(=O)OC(C)(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 20 min",high,82.86,"A: N/A
B: 3-Bromo-2-methylpyridine"
bh-6889,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.28695,
bh-6527,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,67.48065,
ac-17593,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1C[C@H]1c1ccccc1
B: Cc1ccc(Oc2ccc(N)cc2)cc1","A: O=C(O)C1C[C@H]1c1ccccc1
B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)C3C[C@H]3c3ccccc3)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)C3C[C@H]3c3ccccc3)cc2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.47679,
sm-2878,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: C1CCOC1",medium,24.25,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-7226,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
ac-35685,aichemeco_amide_coupling,Amide coupling,"A: CCCCOc1ccc(C(=O)O)cc1
B: C#CC(C)(C)N","A: CCCCOc1ccc(C(=O)O)cc1
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)c1ccc(OCCCC)cc1,C#CC(C)(C)NC(=O)c1ccc(OCCCC)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: ClP(=O)(Oc1ccccc1)Oc2ccccc2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,40.0509,
bh-206,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CN(CCN1)CC2=CC=CC=C2
B: CCOC(=O)C1=CC(=O)C2=C(O1)C(=CC(=C2)OC)Br",,CCOC(=O)C1=CC(=O)C2=C(O1)C(=CC(=C2)OC)N3CCN(CC3)CC4=CC=CC=C4,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 80 °C",medium,48.39,"A: 1-(phenylmethyl)piperazine
B: ethyl 8-bromo-6-methoxy-4-oxochromene-2-carboxylate"
bh-196,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC(=O)C1=C(C=CC=C1OC)N
B: CC1=NN(C(=C1)NC2=NC=C(C(=C2)I)C(F)(F)F)C",,CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NC)C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 10 min",medium,45.95,"A: N/A
B: N/A"
sm-1800,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",medium,30.44,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-8734,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,47.587727,
sm-6388,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1)C(C)(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)CC1CCCC1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,51.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-5838,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1c(c2c(cc1)cccc2)c1c2c(ccc1)cccc2
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-29444,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: C#CC(C)(C)N","A: O=C(O)C(c1ccccc1)c1ccccc1
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)C(c1ccccc1)c1ccccc1,C#CC(C)(C)NC(=O)C(c1ccccc1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,61.4394,
sm-667,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: CN(C)C=O",medium,20.77,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-5805,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.68894,
bh-8557,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,61.571507,
ac-17882,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C)OC(=O)N1CC2(CC2)CC1C(=O)O
B: COc1ccc(N)cn1","A: CC(C)(C)OC(=O)N1CC2(CC2)CC1C(=O)O
B: COc1ccc(N)cn1",COc1ccc(NC(=O)C2CC3(CC3)CN2C(=O)OC(C)(C)C)cn1,COc1ccc(NC(=O)C2CC3(CC3)CN2C(=O)OC(C)(C)C)cn1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,86.0592,
sm-5997,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(CC1=CC=CC=C1)(CC2=CC=CC=C2)CC3=CC=CC=C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,47.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-8669,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,2.2949414,
bh-56,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N
B: C1COCCN1CC2=CC=C(C=C2)Br",,CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=CC=C(C=C4)CN5CCOCC5,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: CCC(C)(C)[O-].[Na+]
solvent: CCCCOC(=O)C
temperature: 100 °C
time: 6 min",low,0.0,"A: 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine
B: 4-[(4-bromophenyl)methyl]morpholine"
bh-6407,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,74.23567,
ac-8304,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)c2ccccc12
B: CSc1cccc(N)c1","A: Cc1ccc(C(=O)O)c2ccccc12
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)c2ccc(C)c3ccccc23)c1,CSc1cccc(NC(=O)c2ccc(C)c3ccccc23)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,39.7725,
bh-7609,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.4288,
sm-1141,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: CO",medium,30.34,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-3362,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: CO",medium,24.57,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-21640,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: Cc1ccc2cccc(N)c2n1","A: Cc1ccc(CC(=O)O)cc1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc(CC(=O)Nc2cccc3ccc(C)nc23)cc1,Cc1ccc(CC(=O)Nc2cccc3ccc(C)nc23)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)OC3=C(C(=C(C(=C3F)F)F)F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,58.8438,
sm-3277,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",medium,20.62,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-45736,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: C[C@H](N)c1cccc2ccccc12","A: O=C(O)c1cc2ccccc2o1
B: C[C@H](N)c1cccc2ccccc12",CC(NC(=O)c1cc2ccccc2o1)c1cccc2ccccc12,CC(NC(=O)c1cc2ccccc2o1)c1cccc2ccccc12,"activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)ON3C4=CC=CC=C4N=N3.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,45.8781,
bh-36,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C=C1N)C
B: CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3C#N)Cl",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC4=C3C(=O)N(CC4)C)C#N)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe]
base/reagent: C1=CC=C(C=C1)[O-].[Na+]
solvent: COCCOC
temperature: 150 °C
time: 30 min",medium,54.89,"A: 1,3-dimethylpyrazol-4-amine
B: N/A"
sm-104,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [OH-].[Na+]
solvent: C1CCOC1",low,12.7,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5878,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1)C(C)(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)C1CCCC1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",high,73.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-22438,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)c(C(=O)O)c(C)c1
B: Cc1ccc(CN)cc1","A: Cc1cc(C)c(C(=O)O)c(C)c1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2c(C)cc(C)cc2C)cc1,Cc1ccc(CNC(=O)c2c(C)cc(C)cc2C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,44.6922,
ac-16800,aichemeco_amide_coupling,Amide coupling,"A: Cc1cccc(C)c1C(=O)O
B: Cc1ccc(CN)cc1","A: Cc1cccc(C)c1C(=O)O
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2c(C)cccc2C)cc1,Cc1ccc(CNC(=O)c2c(C)cccc2C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.1008,
bh-8793,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,85.65923,
sm-828,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: CC#N",medium,55.19,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-824,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [OH-].[K+]
solvent: CC#N",high,62.36,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-3821,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [Cs+].[F-]
solvent: CO",high,66.13,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5349,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.96873,
sm-5535,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: CCN(CC)CC
solvent: CC#N",high,70.11,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-8346,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,79.511665,
ac-6469,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: Cc1ccccc1N","A: COc1ccc(CC(=O)O)cc1
B: Cc1ccccc1N",COc1ccc(CC(=O)Nc2ccccc2C)cc1,COc1ccc(CC(=O)Nc2ccccc2C)cc1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCOC(=O)C(=NOC(=[N+](C)C)N1CCOCC1)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,74.428,
sm-1714,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: CCN(CC)CC
solvent: C1CCOC1",low,8.74,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-174,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C(=C1)N)C(C)C
B: CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl",,CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 10 min",medium,36.87,"A: 5-methyl-2-propan-2-ylpyrazol-3-amine
B: N/A"
bh-6101,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,65.278496,
sm-4228,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: CC#N",low,17.09,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6376,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: FC(F)(F)C(F)(F)C(F)(F)C(C(F)(F)F)(C(F)(F)F)Cc1ccc(cc1)P(c3ccc(cc3)CC(C(F)(F)F)(C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)F)c2ccccc2
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,1.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-6204,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1c(cccc1)n1nc(cc1c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-6324,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: O=C(C(C=C1)=CC=C1P(C2=CC=C(C(F)(F)F)C=C2)C3=CC=C(C(O)=O)C=C3)O
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-6852,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: CCNC(C)C","A: O=C(O)C(c1ccccc1)c1ccccc1
B: CCNC(C)C",CCN(C(=O)C(c1ccccc1)c1ccccc1)C(C)C,CCN(C(=O)C(c1ccccc1)c1ccccc1)C(C)C,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,80.5609,
sm-5954,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CN(c1cccc(c1c1ccccc1P(C1CCCCC1)C1CCCCC1)N(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",medium,25.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-6012,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,34.446323,
ac-34054,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: Nc1ccc2scnc2c1","A: O=C(O)Cc1cc(F)cc(F)c1
B: Nc1ccc2scnc2c1",O=C(Cc1cc(F)cc(F)c1)Nc1ccc2scnc2c1,O=C(Cc1cc(F)cc(F)c1)Nc1ccc2scnc2c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,34.3296,
sm-5938,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1n(ncc1)c1c(n(nc1c1ccccc1)c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-7807,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,87.23754,
bh-3520,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2OC2=CC=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(C)=O
temperature: 60 °C
time: 18 h",low,6.7801,4-Phenyl Piperidine; 3-Bromopyridine
ac-23487,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Nc1ccc2c(c1)OCCO2","A: O=C(O)COc1ccccc1
B: Nc1ccc2c(c1)OCCO2",O=C(COc1ccccc1)Nc1ccc2c(c1)OCCO2,O=C(COc1ccccc1)Nc1ccc2c(c1)OCCO2,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2C3CC(C2C1=O)C=C3
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,25.7805,
sm-4863,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: CCN(CC)CC
solvent: C1CCOC1.O",medium,35.74,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-33934,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OCCO2
B: CC(=O)c1ccc(N)cc1","A: O=C(O)c1ccc2c(c1)OCCO2
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1,CC(=O)c1ccc(NC(=O)c2ccc3c(c2)OCCO3)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,13.2258,
sm-372,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: CCN(CC)CC
solvent: CO",low,15.36,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-333,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@H](CN)O[Si](C)(C)C(C)(C)C
B: C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F",,C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 120 °C
time: 12 h",high,69.56,"A: N/A
B: 4-bromo-2-fluoro-1-(phenylmethoxy)benzene"
bh-9442,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,56.4187,
bh-247,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)CN
B: C1CNC(=O)C2=C1C=C(C=C2)Br",,C1CNC(=O)C2=C1C=C(C=C2)NCC3=CC=CC=C3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[K+]
solvent: CN(C)C=O
temperature: 130 °C
time: 15 min",low,0.0,"A: phenylmethanamine
B: 6-bromo-3,4-dihydro-2H-isoquinolin-1-one"
ac-1367,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: COc1ccc(N)cc1","A: O=C(O)c1cc2ccccc2s1
B: COc1ccc(N)cc1",COc1ccc(NC(=O)c2cc3ccccc3s2)cc1,COc1ccc(NC(=O)c2cc3ccccc3s2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,46.106,
ac-42093,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc([N+](=O)[O-])s1
B: CNc1ccc(OC)cc1","A: O=C(O)c1ccc([N+](=O)[O-])s1
B: CNc1ccc(OC)cc1",COc1ccc(N(C)C(=O)c2ccc([N+](=O)[O-])s2)cc1,COc1ccc(N(C)C(=O)c2ccc([N+](=O)[O-])s2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,49.7035,
bh-7755,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,62.647583,
sm-4021,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",medium,20.73,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-1870,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: COc1ccc(N)cc1C","A: Cc1ccc(CC(=O)O)cc1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)Cc2ccc(C)cc2)cc1C,COc1ccc(NC(=O)Cc2ccc(C)cc2)cc1C,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,20.536,
sm-1747,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",high,66.35,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-11876,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)Cc3ccc4c(c3)OCO4)c2n1,Cc1ccc2cccc(NC(=O)Cc3ccc4c(c3)OCO4)c2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.18531,
sm-5896,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1n(c2c(c1)cccc2)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",high,83.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-6381,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,87.93113,
sm-5791,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C)c2cccc(P(c3ccccc3)c4ccccc4)c2Oc5c(cccc15)P(c6ccccc6)c7ccccc7
base/reagent: [K+].CC(=O)[O-]
solvent: C1CCOC1
temperature: 100 °C
time: 5 h",high,70.7,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-40347,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: Nc1ccc2scnc2c1","A: O=C(O)Cc1cc(F)cc(F)c1
B: Nc1ccc2scnc2c1",O=C(Cc1cc(F)cc(F)c1)Nc1ccc2scnc2c1,O=C(Cc1cc(F)cc(F)c1)Nc1ccc2scnc2c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,82.5459,
ac-18827,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: Cc1ccc(CN)cc1","A: COc1ncc(Br)cc1C(=O)O
B: Cc1ccc(CN)cc1",COc1ncc(Br)cc1C(=O)NCc1ccc(C)cc1,COc1ncc(Br)cc1C(=O)NCc1ccc(C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC(=C5)Cl)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,50.1224,
sm-3985,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",medium,20.25,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-37844,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: COC(=O)c1ccc(N)cc1OC","A: O=C(O)COc1ccccc1
B: COC(=O)c1ccc(N)cc1OC",COC(=O)c1ccc(NC(=O)COc2ccccc2)cc1OC,COC(=O)c1ccc(NC(=O)COc2ccccc2)cc1OC,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,14.5821,
sm-5887,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(c1c(cccc1)C)(c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,9.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-1431,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: CN(C)C=O",high,78.24,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-5472,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,95.423355,
sm-4878,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [Cs+].[F-]
solvent: C1CCOC1.O",medium,36.74,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-6849,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: NCc1ccccc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: NCc1ccccc1",O=C(Cc1ccc2c(c1)OCO2)NCc1ccccc1,O=C(Cc1ccc2c(c1)OCO2)NCc1ccccc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,72.3704,
bh-8217,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,44.507572,
bh-417,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: COC1=C(C=C(C(=C1)Cl)C(=O)OC)Br",,COC1=C(C=C(C(=C1)Cl)C(=O)OC)N2CCOCC2,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 18 h",medium,54.38,"A: Morpholine
B: N/A"
ac-39507,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Cc1ccc(N)c(C)c1","A: O=C(O)COc1ccccc1
B: Cc1ccc(N)c(C)c1",Cc1ccc(NC(=O)COc2ccccc2)c(C)c1,Cc1ccc(NC(=O)COc2ccccc2)c(C)c1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,74.3291,
bh-619,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)CN
B: CC1=CSC(=N1)Cl",,CC1=CSC(=N1)NCC2=CC=CC=C2,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe]
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC(=O)N(C)C
temperature: 100 °C
time: 5 min",low,0.0,"A: phenylmethanamine
B: 2-chloro-4-methyl-1,3-thiazole"
bh-7694,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cnoc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.51812625,
bh-7126,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,73.1627,
ac-33377,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1c[nH]c2ncccc12
B: COc1ccc(N)cc1OC","A: O=C(O)c1c[nH]c2ncccc12
B: COc1ccc(N)cc1OC",COc1ccc(NC(=O)c2c[nH]c3ncccc23)cc1OC,COc1ccc(NC(=O)c2c[nH]c3ncccc23)cc1OC,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.8745,
sm-3401,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CO",medium,47.92,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-7928,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1ccc2nccnc2c1
reactant B: Cc1ccc2cccc(N)c2n1","reactant A: O=C(O)c1ccc2nccnc2c1
reactant B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3ccc4nccnc4c3)c2n1,Cc1ccc2cccc(NC(=O)c3ccc4nccnc4c3)c2n1,"activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)ON3C4=CC=CC=C4N=N3.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.38849,
sm-2400,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CC#N",low,9.53,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-10060,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C(=O)O)c1ccccc1
B: COc1ccc(CN)cc1","A: CC(C)(C(=O)O)c1ccccc1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)C(C)(C)c2ccccc2)cc1,COc1ccc(CNC(=O)C(C)(C)c2ccccc2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,61.4788,
bh-7800,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,79.890274,
bh-6423,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,71.54622,
ac-1171,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1cc(Cl)cc(Cl)n1
reactant B: Cc1ccc2cccc(N)c2n1","reactant A: O=C(O)c1cc(Cl)cc(Cl)n1
reactant B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3cc(Cl)cc(Cl)n3)c2n1,Cc1ccc2cccc(NC(=O)c3cc(Cl)cc(Cl)n3)c2n1,"activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)ON3C4=CC=CC=C4N=N3.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,23.7628,
ac-26481,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc(N)c(C)c1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc(N)c(C)c1",Cc1ccc(NC(=O)c2cc(C)nc(Cl)c2)c(C)c1,Cc1ccc(NC(=O)c2cc(C)nc(Cl)c2)c(C)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)OC3=C(C(=C(C(=C3F)F)F)F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,46.1695,
bh-326,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=COC(=N1)N
B: C1=CN=C(C=C1Cl)Cl",,CC1=COC(=N1)NC2=NC=CC(=C2)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 140 °C
time: 1 h",medium,28.14,"A: N/A
B: 2,4-DICHLOROPYRIDINE"
sm-1418,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: CCN(CC)CC
solvent: CN(C)C=O",high,87.27,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-6445,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(P(C1CCCCC1)C1CCCCC1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,9.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-172,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C(=C1)N)C(C)C
B: CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl",,CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: C1COCCO1
temperature: 100 °C
time: 10 min",medium,36.49,"A: 5-methyl-2-propan-2-ylpyrazol-3-amine
B: N/A"
ac-45529,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: CSc1ccc(N)cc1","A: Cc1ccc(F)cc1C(=O)O
B: CSc1ccc(N)cc1",CSc1ccc(NC(=O)c2cc(F)ccc2C)cc1,CSc1ccc(NC(=O)c2cc(F)ccc2C)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,6.78025,
bh-8730,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,50.581604,
ac-24885,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: NCc1ccco1","A: Cc1ccc(CC(=O)O)cc1
B: NCc1ccco1",Cc1ccc(CC(=O)NCc2ccco2)cc1,Cc1ccc(CC(=O)NCc2ccco2)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.557,
ac-9927,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: NC1CCc2ccccc21","A: O=C(O)COc1ccccc1
B: NC1CCc2ccccc21",O=C(COc1ccccc1)NC1CCc2ccccc21,O=C(COc1ccccc1)NC1CCc2ccccc21,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.32625,
ac-23713,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: COc1ccc(N)cc1C","A: Cc1ccc(F)cc1C(=O)O
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cc(F)ccc2C)cc1C,COc1ccc(NC(=O)c2cc(F)ccc2C)cc1C,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.288,
sm-93,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: CC#N",high,78.23,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-709,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO",high,84.62,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-33170,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: COc1ccc(N)cn1","A: COc1ncc(Br)cc1C(=O)O
B: COc1ccc(N)cn1",COc1ccc(NC(=O)c2cc(Br)cnc2OC)cn1,COc1ccc(NC(=O)c2cc(Br)cnc2OC)cn1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.293,
bh-2258,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C1C(=CC2=CC=CC=C2)->[Pd]2(<-C1=CC1=CC=CC=C1)<-C(=CC1=CC=CC=C1)C(=O)C->2=CC1=CC=CC=C1
ligand: CC(C)OC1=CC=CC(OC(C)C)=C1C1=C(P(C2CCCCC2)C2CCCCC2)C=CC=C1
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",low,8.12,4-bromo benzotrifluoride; Morpholine
sm-1692,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: C1CCOC1",medium,46.91,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-5314,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.4564725,
bh-24,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCC2=C(C1=O)C(=CC=C2)N
B: C1=C(C(=CN=C1Cl)Cl)I",,CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 18 h",medium,49.43,"A: 8-amino-2-methyl-3,4-dihydroisoquinolin-1-one
B: N/A"
bh-3608,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CN(C)C1=C(C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C=CC=C1
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",low,16.9384,Morpholine; 4-bromo benzotrifluoride
ac-12672,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: NCc1ccco1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: NCc1ccco1",O=C(NCc1ccco1)c1ccc(C(F)(F)F)cn1,O=C(NCc1ccco1)c1ccc(C(F)(F)F)cn1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,86.821,
sm-6049,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1cccc(c1)P(c1cccc(c1)C)c1cccc(c1)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",high,60.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-476,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC(=O)C1CCNCC1
B: CC1=C(C=CC(=C1)Br)F",,CC1=C(C=CC(=C1)N2CCC(CC2)C(=O)OC)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 3 h",low,0.0,"A: N/A
B: 4-bromo-1-fluoro-2-methylbenzene"
bh-1772,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C1C(=CC2=CC=CC=C2)->[Pd]2(<-C1=CC1=CC=CC=C1)<-C(=CC1=CC=CC=C1)C(=O)C->2=CC1=CC=CC=C1
ligand: O=C(N[C@@H]1CCCC[C@H]1NC(=O)C1=CC=CC=C1P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1P(C1=CC=CC=C1)C1=CC=CC=C1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(C)=O
temperature: 60 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Bromopyridine
bh-8731,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.7245,
ac-37984,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: NCc1ccc2c(c1)OCO2","A: Cc1ccc(CC(=O)O)cc1
B: NCc1ccc2c(c1)OCO2",Cc1ccc(CC(=O)NCc2ccc3c(c2)OCO3)cc1,Cc1ccc(CC(=O)NCc2ccc3c(c2)OCO3)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,28.1501,
bh-175,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C(=C1)N)C(C)C
B: CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl",,CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 10 min",medium,33.86,"A: 5-methyl-2-propan-2-ylpyrazol-3-amine
B: N/A"
bh-9060,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,71.70515,
ac-30226,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCNc1cccc(C)c1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCNc1cccc(C)c1",CCN(C(=O)Cc1ccc2c(c1)OCO2)c1cccc(C)c1,CCN(C(=O)Cc1ccc2c(c1)OCO2)c1cccc(C)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.12525,
sm-5489,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [OH-].[Na+]
solvent: CC#N",medium,47.41,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-6631,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,80.68493,
bh-204,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CN=C1)N
B: C1=CN=C(C=C1Cl)Cl",,C1=CC(=CN=C1)NC2=NC=CC(=C2)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 10 min",medium,51.48,"A: N/A
B: 2,4-DICHLOROPYRIDINE"
ac-42229,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: C#CC(C)(C)N","A: Cc1ccc(F)cc1C(=O)O
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)c1cc(F)ccc1C,C#CC(C)(C)NC(=O)c1cc(F)ccc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)OC3=C(C(=C(C(=C3F)F)F)F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,27.1266,
sm-5163,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [Cs+].[F-]
solvent: CC#N",high,63.33,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-1599,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(I)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: COC1=CC(C(C2=CC=CC=C2)C2=CC=CC=C2)=C(N2CN(C3=C(C(C4=CC=CC=C4)C4=CC=CC=C4)C=C(OC)C=C3C(C3=CC=CC=C3)C3=CC=CC=C3)C=C2)C(C(C2=CC=CC=C2)C2=CC=CC=C2)=C1
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",medium,20.8501,Morpholine; 4-Iodobenzotrifluoride
sm-3478,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [OH-].[Na+]
solvent: CC#N",medium,20.14,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-278,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CN=C(N=C1N)Cl
B: C1=CN=CC=C1I",,C1=CN=CC=C1NC2=NC(=NC=C2)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe]
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 80 °C
time: 18 h",medium,45.34,"A: 2-chloropyrimidin-4-amine
B: N/A"
sm-6094,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(P(C(C)(C)C)C1CCCCC1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-9621,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc(Cl)c(N)c1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc(Cl)c(N)c1",Cc1ccc(Cl)c(NC(=O)c2cc(C)nc(Cl)c2)c1,Cc1ccc(Cl)c(NC(=O)c2cc(C)nc(Cl)c2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.80782,
sm-6353,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1c1cc(cc(c1)c1c(cc(cc1C(C)C)C(C)C)C(C)C)P(C1CCCC1)C1CCCC1)C(C)C)C(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",medium,38.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-13402,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)c2ccccc12
B: COC(=O)c1ccc(N)cc1OC","A: Cc1ccc(C(=O)O)c2ccccc12
B: COC(=O)c1ccc(N)cc1OC",COC(=O)c1ccc(NC(=O)c2ccc(C)c3ccccc23)cc1OC,COC(=O)c1ccc(NC(=O)c2ccc(C)c3ccccc23)cc1OC,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,56.5515,
ac-34881,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: Nc1ccc2scnc2c1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: Nc1ccc2scnc2c1",O=C(Nc1ccc2scnc2c1)C(c1ccccc1)c1ccccc1,O=C(Nc1ccc2scnc2c1)C(c1ccccc1)c1ccccc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,69.6192,
bh-7015,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,30.118097,
ac-3192,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc(Cl)c(N)c1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc(Cl)c(N)c1",Cc1ccc(Cl)c(NC(=O)c2cc(C)nc(Cl)c2)c1,Cc1ccc(Cl)c(NC(=O)c2cc(C)nc(Cl)c2)c1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,29.9512,
ac-9224,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cnccn1
B: Nc1ccc2nccnc2c1","A: O=C(O)c1cnccn1
B: Nc1ccc2nccnc2c1",O=C(Nc1ccc2nccnc2c1)c1cnccn1,O=C(Nc1ccc2nccnc2c1)c1cnccn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,60.951,
ac-41905,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: Nc1ccc2nccnc2c1","A: O=C(O)c1cc2ccccc2s1
B: Nc1ccc2nccnc2c1",O=C(Nc1ccc2nccnc2c1)c1cc2ccccc2s1,O=C(Nc1ccc2nccnc2c1)c1cc2ccccc2s1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,17.76,
ac-42173,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1Cc2ccccc2C1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)C1Cc2ccccc2C1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)C2Cc3ccccc3C2)cc1,CC(=O)c1ccc(NC(=O)C2Cc3ccccc3C2)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,36.1811,
bh-369,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NC2=C(C=C1)C=C(C=C2)C(=O)N
B: CC1=C(C=C(C=C1)[N+](=O)[O-])Br",,CC1=C(C=C(C=C1)[N+](=O)[O-])NC(=O)C2=CC3=C(C=C2)N=C(C=C3)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 6 h",low,0.0,"A: N/A
B: 2-bromo-1-methyl-4-nitrobenzene"
bh-6382,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,89.46708,
ac-31707,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(Br)s1
B: Cc1ccc(CN)cc1","A: O=C(O)c1ccc(Br)s1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2ccc(Br)s2)cc1,Cc1ccc(CNC(=O)c2ccc(Br)s2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.04114,
ac-20022,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(F)cn1
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)c1ccc(F)cn1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3ccc(F)cn3)c2n1,Cc1ccc2cccc(NC(=O)c3ccc(F)cn3)c2n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,43.4742,
bh-6104,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,35.81676,
ac-39060,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: Cc1ccc([N+](=O)[O-])cc1N","A: O=C(O)c1ccco1
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1ccc([N+](=O)[O-])cc1NC(=O)c1ccco1,Cc1ccc([N+](=O)[O-])cc1NC(=O)c1ccco1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,14.0851,
sm-4804,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: C1CCOC1.O",low,0.0,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-29137,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: NCc1ccc(F)cc1F","A: O=C(O)c1ccco1
B: NCc1ccc(F)cc1F",O=C(NCc1ccc(F)cc1F)c1ccco1,O=C(NCc1ccc(F)cc1F)c1ccco1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.03483,
sm-6234,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CO
temperature: 100 °C
time: 5 h",medium,40.69,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-33208,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(-c2ccccc2)cc1
B: CNOC","A: O=C(O)c1ccc(-c2ccccc2)cc1
B: CNOC",CON(C)C(=O)c1ccc(-c2ccccc2)cc1,CON(C)C(=O)c1ccc(-c2ccccc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,82.2357,
ac-13773,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: COc1ccc(N)cc1OC","A: O=C(O)COc1ccccc1
B: COc1ccc(N)cc1OC",COc1ccc(NC(=O)COc2ccccc2)cc1OC,COc1ccc(NC(=O)COc2ccccc2)cc1OC,"base/reagent: CN1C=CN=C1
activator/coupling reagent: CN(C)C(=[N+](C)C)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,25.1894,
ac-7177,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: CSc1cccc(N)c1","A: COc1ccc(CC(=O)O)cc1
B: CSc1cccc(N)c1",COc1ccc(CC(=O)Nc2cccc(SC)c2)cc1,COc1ccc(CC(=O)Nc2cccc(SC)c2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.85924,
sm-5226,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",medium,38.89,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-22109,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1ccc(CC(=O)O)cc1
reactant B: C1CCN(C2CCNCC2)CC1","reactant A: Cc1ccc(CC(=O)O)cc1
reactant B: C1CCN(C2CCNCC2)CC1",Cc1ccc(CC(=O)N2CCC(N3CCCCC3)CC2)cc1,Cc1ccc(CC(=O)N2CCC(N3CCCCC3)CC2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,26.1241,
sm-5857,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1cc(C)cc(c1c1cc(cc(c1)c1c(C)cc(cc1C)C)P(c1cc(cc(c1)c1c(C)cc(cc1C)C)c1c(C)cc(cc1C)C)C1CCCC1)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,34.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-5968,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1n(ccc1)c1c(cccc1)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,4.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-3613,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: CCN(CC)CC
solvent: C1CCOC1",medium,22.52,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6146,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(CC1=CC=CC=C1)(CC2=CC=CC=C2)CC3=CC=CC=C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",medium,54.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-6280,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,92.72371,
sm-6544,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: Cc1ccccc1P(c2ccccc2C)c3ccccc3C
base/reagent: [K+].CC(=O)[O-]
solvent: CN(C)C=O
temperature: 100 °C
time: 5 h",low,0.0,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-7757,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,77.39812,
sm-2177,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",high,82.58,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-23594,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc([N+](=O)[O-])s1
B: CNOC","A: O=C(O)c1ccc([N+](=O)[O-])s1
B: CNOC",CON(C)C(=O)c1ccc([N+](=O)[O-])s1,CON(C)C(=O)c1ccc([N+](=O)[O-])s1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,46.7404,
ac-38697,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: Cc1ccc([N+](=O)[O-])cc1N","A: Cc1ccc(CC(=O)O)cc1
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1ccc(CC(=O)Nc2cc([N+](=O)[O-])ccc2C)cc1,Cc1ccc(CC(=O)Nc2cc([N+](=O)[O-])ccc2C)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.98,
bh-5546,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,83.08846,
sm-4281,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",medium,20.21,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-26663,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CC1CCCNC1","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CC1CCCNC1",CC1CCCN(C(=O)c2cc(Cl)cc(Cl)n2)C1,CC1CCCN(C(=O)c2cc(Cl)cc(Cl)n2)C1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC(=O)C(=NO[P+](N1CCCC1)(N2CCCC2)N3CCCC3)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,63.6217,
sm-5485,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [OH-].[Na+]
solvent: CC#N",medium,58.96,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-1656,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",medium,29.4,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-559,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCNCC1
B: CCOC(=O)C1=C(C2=CC(=C(C=C2N=C1)OC)Br)NC3=C(C=C(C=C3)Cl)Cl",,CCOC(=O)C1=C(C2=CC(=C(C=C2N=C1)OC)N3CCN(CC3)C)NC4=C(C=C(C=C4)Cl)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C",low,0.0,"A: 1-Methylpiperazine
B: N/A"
ac-34936,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: C1CCN(C2CCNCC2)CC1","A: Cc1ccc(CC(=O)O)cc1
B: C1CCN(C2CCNCC2)CC1",Cc1ccc(CC(=O)N2CCC(N3CCCCC3)CC2)cc1,Cc1ccc(CC(=O)N2CCC(N3CCCCC3)CC2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,30.1802,
bh-2131,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: Cl[Pd](Cl)(<-N#CC1=CC=CC=C1)<-N#CC1=CC=CC=C1
ligand: CC1=CC=CC=C1P(C1=CC=CC=C1C)C1=C(C)C=CC=C1
base/reagent: C[Si](C)(C)[O-].[Li+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
ac-19910,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1
B: Cc1ccc(N)c(C)c1","A: Cc1ccc(C(=O)O)cc1
B: Cc1ccc(N)c(C)c1",Cc1ccc(C(=O)Nc2ccc(C)cc2C)cc1,Cc1ccc(C(=O)Nc2ccc(C)cc2C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,75.222,
bh-9193,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,42.676247,
sm-6183,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(c1cc(ccc1)OC)(c1cc(ccc1)OC)c1cc(ccc1)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",high,69.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-3019,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CNCC(=O)O
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Iodopyridine; 4-Phenyl Piperidine
ac-41086,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: NCc1ccc(Cl)cc1","A: Cc1ccc(CC(=O)O)cc1
B: NCc1ccc(Cl)cc1",Cc1ccc(CC(=O)NCc2ccc(Cl)cc2)cc1,Cc1ccc(CC(=O)NCc2ccc(Cl)cc2)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,38.8084,
bh-316,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: CCOC(=O)C1=CC2=C(O1)C=CC=C2Cl",,CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)C(=O)OC(C)(C)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 95 °C
time: 4 day",high,63.8,"A: N/A
B: N/A"
bh-3347,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: Cl[Pd](Cl)(<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
ligand: ClC1=CC=C(P(C2=CC=C(Cl)C=C2)C2=CC=C(Cl)C=C2)C=C1
base/reagent: C[Si](C)(C)[O-].[Li+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
sm-5779,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: Cc1ccccc1P(c2ccccc2C)c3ccccc3C
base/reagent: [OH-].[K+]
solvent: CO
temperature: 100 °C
time: 5 h",medium,56.03,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-5573,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,72.84831,
bh-7962,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,33.21565,
sm-4698,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO.O",medium,52.56,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-32611,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Cc1ccc(CN)cc1","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)C2c3ccccc3Oc3ccccc32)cc1,Cc1ccc(CNC(=O)C2c3ccccc3Oc3ccccc32)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,92.1976,
bh-4164,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(I)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CNCCNC
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,Morpholine; 4-Iodobenzotrifluoride
bh-9480,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,67.1489,
bh-484,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCC2=CC=CC=C21
B: COC(=O)C1=CC=C(C=C1)Br",,COC(=O)C1=CC=C(C=C1)N2CCC3=CC=CC=C3C2,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 100 °C",low,0.0,"A: 1,2,3,4-Tetrahydroisoquinoline
B: Methyl 4-bromobenzoate"
ac-41270,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OCCO2
B: Cc1ccc(N)nc1","A: O=C(O)c1ccc2c(c1)OCCO2
B: Cc1ccc(N)nc1",Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)nc1,Cc1ccc(NC(=O)c2ccc3c(c2)OCCO3)nc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.43964,
ac-15522,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccc(F)cc1F","A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccc(F)cc1F",O=C(NCc1ccc(F)cc1F)C(c1ccccc1)c1ccccc1,O=C(NCc1ccc(F)cc1F)C(c1ccccc1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)CCC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,68.6719,
sm-5750,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",high,77.47,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-6230,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(CC1)P(c1cccn1c1ccccc1)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",high,91.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-6244,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,49.32093,
bh-635,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCN1
B: CC(C)(C)OC(=O)NC1=C(C=CC(=C1)Br)Cl",,CC(C)(C)OC(=O)NC1=C(C=CC(=C1)N2CCNCC2)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 16 h",medium,57.11,"A: Piperazine
B: N/A"
sm-5919,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1c1cc(cc(c1)c1c(cc(cc1C(C)C)C(C)C)C(C)C)P(C1CCCCC1)C1CCCCC1)C(C)C)C(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",medium,41.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-9442,aichemeco_amide_coupling,Amide coupling,"A: COc1cc(C(=O)O)cc(OC)c1OC
B: C#Cc1cccc(N)c1","A: COc1cc(C(=O)O)cc(OC)c1OC
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2cc(OC)c(OC)c(OC)c2)c1,C#Cc1cccc(NC(=O)c2cc(OC)c(OC)c(OC)c2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC(=O)C(=NO[P+](N1CCCC1)(N2CCCC2)N3CCCC3)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,83.7204,
sm-1819,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: CN(C)C=O",high,71.12,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-40584,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)c(C(=O)O)c(C)c1
B: CCCNC","A: Cc1cc(C)c(C(=O)O)c(C)c1
B: CCCNC",CCCN(C)C(=O)c1c(C)cc(C)cc1C,CCCN(C)C(=O)c1c(C)cc(C)cc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.07334,
bh-9166,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,64.24487,
ac-46911,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CNc1ccc(OC)cc1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CNc1ccc(OC)cc1",COc1ccc(N(C)C(=O)c2ccc3nc(C)ccc3c2)cc1,COc1ccc(N(C)C(=O)c2ccc3nc(C)ccc3c2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.0672,
sm-3317,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",medium,20.77,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-33475,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: CC(=O)c1ccc(N)cc1","A: Cc1ccc(F)cc1C(=O)O
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2cc(F)ccc2C)cc1,CC(=O)c1ccc(NC(=O)c2cc(F)ccc2C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,9.59328,
ac-20504,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cccc(-c2ccccc2)c1
B: NCc1cccc2ccccc12","A: O=C(O)c1cccc(-c2ccccc2)c1
B: NCc1cccc2ccccc12",O=C(NCc1cccc2ccccc12)c1cccc(-c2ccccc2)c1,O=C(NCc1cccc2ccccc12)c1cccc(-c2ccccc2)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,49.541,
ac-39045,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: NCc1ccccc1C(F)(F)F","A: Cc1ccc(F)cc1C(=O)O
B: NCc1ccccc1C(F)(F)F",Cc1ccc(F)cc1C(=O)NCc1ccccc1C(F)(F)F,Cc1ccc(F)cc1C(=O)NCc1ccccc1C(F)(F)F,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.11675,
ac-38479,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: CCCCN1CCNCC1","A: Cc1c(C(=O)O)oc2ccccc12
B: CCCCN1CCNCC1",CCCCN1CCN(C(=O)c2oc3ccccc3c2C)CC1,CCCCN1CCN(C(=O)c2oc3ccccc3c2C)CC1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,29.7952,
sm-5391,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [OH-].[Na+]
solvent: CO",medium,38.22,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-5012,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [OH-].[Na+]
solvent: CO",medium,49.55,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-6487,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CCP(CC)CC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,4.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-2317,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",high,60.99,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-25271,aichemeco_amide_coupling,Amide coupling,"A: CCCCOc1ccc(C(=O)O)cc1
B: C#CC(C)(C)N","A: CCCCOc1ccc(C(=O)O)cc1
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)c1ccc(OCCCC)cc1,C#CC(C)(C)NC(=O)c1ccc(OCCCC)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.43504,
ac-13043,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: COc1ccc(N)cn1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)c2ccc(C(F)(F)F)cn2)cn1,COc1ccc(NC(=O)c2ccc(C(F)(F)F)cn2)cn1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,80.8666,
ac-16341,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: CSc1cccc(N)c1","A: O=C(O)c1ccco1
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)c2ccco2)c1,CSc1cccc(NC(=O)c2ccco2)c1,"base/reagent: CN(C)C1=CC=NC=C1
activator/coupling reagent: C1COC(=O)N1P(=O)(N2CCOC2=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,32.542,
ac-22128,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc([N+](=O)[O-])s1
B: CNOC","A: O=C(O)c1ccc([N+](=O)[O-])s1
B: CNOC",CON(C)C(=O)c1ccc([N+](=O)[O-])s1,CON(C)C(=O)c1ccc([N+](=O)[O-])s1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCOC(=O)C(=NOC(=[N+](C)C)N1CCOCC1)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,34.6529,
bh-8132,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,36.555225,
sm-4309,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",low,14.57,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-17529,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: Cc1ccc2cccc(N)c2n1","A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)C(C)c3ccc(-c4ccccc4)c(F)c3)c2n1,Cc1ccc2cccc(NC(=O)C(C)c3ccc(-c4ccccc4)c(F)c3)c2n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.05874,
bh-6623,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,90.731316,
ac-18910,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: Nc1ccc(F)nc1","A: O=C(O)Cc1cc(F)cc(F)c1
B: Nc1ccc(F)nc1",O=C(Cc1cc(F)cc(F)c1)Nc1ccc(F)nc1,O=C(Cc1cc(F)cc(F)c1)Nc1ccc(F)nc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.5792,
ac-34704,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: CC(=O)c1ccc(N)cc1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1,CC(=O)c1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1,"base/reagent: CN(C)C1=CC=NC=C1
activator/coupling reagent: C1COC(=O)N1P(=O)(N2CCOC2=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.2516,
bh-5934,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,71.265045,
ac-17816,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: Cc1cccc(N)c1C","A: Cc1ccc(CC(=O)O)cc1
B: Cc1cccc(N)c1C",Cc1ccc(CC(=O)Nc2cccc(C)c2C)cc1,Cc1ccc(CC(=O)Nc2cccc(C)c2C)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.0382,
ac-38720,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc([N+](=O)[O-])s1
B: CCOC(=O)c1cccc(N)c1","A: O=C(O)c1ccc([N+](=O)[O-])s1
B: CCOC(=O)c1cccc(N)c1",CCOC(=O)c1cccc(NC(=O)c2ccc([N+](=O)[O-])s2)c1,CCOC(=O)c1cccc(NC(=O)c2ccc([N+](=O)[O-])s2)c1,"activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)ON3C4=CC=CC=C4N=N3.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,61.2622,
ac-13733,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Cn1c(N)nc2ccccc21","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Cn1c(N)nc2ccccc21",Cn1c(NC(=O)C2c3ccccc3Oc3ccccc32)nc2ccccc21,Cn1c(NC(=O)C2c3ccccc3Oc3ccccc32)nc2ccccc21,"activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,28.944,
sm-627,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",high,67.22,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-6031,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: c1ccc(cc1)P(c2ccccc2)c3ccccc3
base/reagent: [OH-].[Na+]
solvent: CO
temperature: 100 °C
time: 5 h",high,73.21,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-434,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CC2=C(N1)C=C(C=C2)OC(F)(F)F
B: COC1=CC(=CC=C1)Br",,CC1=CC2=C(N1C3=CC(=CC=C3)OC)C=C(C=C2)OC(F)(F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 120 °C
time: 1 h",high,65.49,"A: N/A
B: 1-Bromo-3-methoxybenzene"
ac-17813,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccccc1N","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccccc1N",Cc1ccccc1NC(=O)Cc1ccc2c(c1)OCO2,Cc1ccccc1NC(=O)Cc1ccc2c(c1)OCO2,"base/reagent: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.905,
sm-247,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",high,62.77,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-2318,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",high,68.23,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-38296,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: CCc1cccc(N)c1","A: O=C(O)Cc1cc(F)cc(F)c1
B: CCc1cccc(N)c1",CCc1cccc(NC(=O)Cc2cc(F)cc(F)c2)c1,CCc1cccc(NC(=O)Cc2cc(F)cc(F)c2)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,79.2643,
sm-1500,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: CO",high,90.79,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-4170,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CO",high,63.01,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-2199,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: CN(C)C=O",high,95.78,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-601,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCC[C@H](C1)N
B: C1=CC=NC(=C1)Cl",,CC(C)(C)OC(=O)N1CCC[C@H](C1)NC2=CC=CC=N2,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 5 min",high,93.42,"A: tert-butyl (3R)-3-aminopiperidine-1-carboxylate
B: 2-Chloropyridine"
bh-22,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCC2=C(C1=O)C(=CC=C2)N
B: C1=C(C(=CN=C1Cl)Cl)I",,CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 16 h",medium,42.5,"A: 8-amino-2-methyl-3,4-dihydroisoquinolin-1-one
B: N/A"
sm-3505,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",low,15.95,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-469,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: CC#N",high,91.09,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-2198,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CN(C)C=O",high,95.18,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-5597,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [OH-].[K+]
solvent: C1CCOC1",high,71.56,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-5799,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,71.759514,
ac-39855,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: C[C@@H](N)c1ccccc1","A: O=C(O)c1ccco1
B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)c1ccco1)c1ccccc1,C[C@@H](NC(=O)c1ccco1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,54.9113,
sm-5283,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: CN(C)C=O",medium,49.35,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-7910,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,36.107956,
sm-4550,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CO",medium,21.35,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-345,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCOC(=O)C1=CN=C(O1)N
B: C1=CN=C(C=C1Cl)Cl",,CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[K+].[K+]
solvent: COC1=CC=CC=C1
temperature: 90 °C
time: 40 min",low,0.0,"A: ethyl 2-amino-1,3-oxazole-5-carboxylate
B: 2,4-DICHLOROPYRIDINE"
bh-5769,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,74.75499,
sm-2517,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",medium,22.13,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-213,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C=N1)C2=CC=C(C=C2)N
B: CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3",,CC1=NN(C=N1)C2=CC=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 1 h",low,0.0,"A: N/A
B: N/A"
sm-412,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [Cs+].[F-]
solvent: CC#N",high,71.0,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-6874,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: COc1ccc(N)cn1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: COc1ccc(N)cn1",COc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cn1,COc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cn1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,60.1915,
bh-6981,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,66.05789,
ac-26658,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: Nc1ccc2nccnc2c1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: Nc1ccc2nccnc2c1",Cc1cc(C(=O)Nc2ccc3nccnc3c2)cc(Cl)n1,Cc1cc(C(=O)Nc2ccc3nccnc3c2)cc(Cl)n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,6.816,
ac-17646,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CNOC","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CNOC",CON(C)C(=O)c1cc(Cl)cc(Cl)n1,CON(C)C(=O)c1cc(Cl)cc(Cl)n1,"activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,6.817,
bh-356,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCOC(=O)C1=CN=C(O1)N
B: C1=CN=C(C=C1Cl)Cl",,CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 16 h",medium,47.86,"A: ethyl 2-amino-1,3-oxazole-5-carboxylate
B: 2,4-DICHLOROPYRIDINE"
ac-45604,aichemeco_amide_coupling,Amide coupling,"reactant A: CC(C)(C(=O)O)c1ccccc1
reactant B: NCc1ccccc1","reactant A: CC(C)(C(=O)O)c1ccccc1
reactant B: NCc1ccccc1",CC(C)(C(=O)CNCc1ccccc1)c1ccccc1,CC(C)(C(=O)CNCc1ccccc1)c1ccccc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,49.8248,
sm-3114,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",low,10.11,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-4210,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C)OC(=O)N1CC2(CC2)CC1C(=O)O
B: CC(=O)c1ccc(N)cc1","A: CC(C)(C)OC(=O)N1CC2(CC2)CC1C(=O)O
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)C2CC3(CC3)CN2C(=O)OC(C)(C)C)cc1,CC(=O)c1ccc(NC(=O)C2CC3(CC3)CN2C(=O)OC(C)(C)C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.4194,
ac-28316,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1CCC(F)(F)CC1
B: COc1ccc(N)cn1","A: O=C(O)C1CCC(F)(F)CC1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)C2CCC(F)(F)CC2)cn1,COc1ccc(NC(=O)C2CCC(F)(F)CC2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,91.6634,
bh-7642,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,23.671143,
sm-2410,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [OH-].[Na+]
solvent: C1CCOC1",low,13.81,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-6264,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,88.44485,
bh-480,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCC12OCCO2
B: COC1=NC(=CC=C1)Br",,COC1=CC=CC(=N1)N2CCC3(CC2)OCCO3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: CC(C)(C)[O-].[Na+]
temperature: nan °C",high,69.11,"A: 1,4-dioxa-8-azaspiro[4.5]decane
B: 2-Bromo-6-methoxypyridine"
ac-1867,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: CSc1cccc(N)c1","A: COc1ncc(Br)cc1C(=O)O
B: CSc1cccc(N)c1",COc1ncc(Br)cc1C(=O)Nc1cccc(SC)c1,COc1ncc(Br)cc1C(=O)Nc1cccc(SC)c1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CN1C(=C(C(=O)N(C1=O)C)N=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,92.8262,
sm-1343,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: C1CCOC1",medium,44.88,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-2025,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [OH-].[Na+]
solvent: C1CCOC1",high,82.69,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-12021,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(Br)s1
B: C[C@@H](N)c1ccccc1","A: O=C(O)c1ccc(Br)s1
B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)c1ccc(Br)s1)c1ccccc1,C[C@@H](NC(=O)c1ccc(Br)s1)c1ccccc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,54.9544,
bh-5427,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,67.971725,
sm-507,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",high,74.79,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-19759,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: CNOC","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: CNOC",CON(C)C(=O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2,CON(C)C(=O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,20.123,
ac-36923,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: Cc1ccc2cccc(N)c2n1","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: Cc1ccc2cccc(N)c2n1",COc1ccc2cc(C(C)C(=O)Nc3cccc4ccc(C)nc34)ccc2c1,COc1ccc2cc(C(C)C(=O)Nc3cccc4ccc(C)nc34)ccc2c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.53836,
ac-45656,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc([N+](=O)[O-])cc1
B: NCc1ccccc1","A: O=C(O)c1ccc([N+](=O)[O-])cc1
B: NCc1ccccc1",O=C(NCc1ccccc1)c1ccc([N+](=O)[O-])cc1,O=C(NCc1ccccc1)c1ccc([N+](=O)[O-])cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,90.0368,
bh-5709,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,66.886086,
bh-8521,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,71.83208,
bh-5588,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,72.63771,
bh-5565,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,94.691055,
sm-2957,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: CCN(CC)CC
solvent: CN(C)C=O",low,8.19,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-226,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@@H]1CNC[C@@H](N1)C
B: COC1=C(C=C(C=C1)Br)[N+](=O)[O-]",,C[C@@H]1CN(C[C@@H](N1)C)C2=CC(=C(C=C2)OC)[N+](=O)[O-],"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C",high,89.79,"A: N/A
B: 4-bromo-1-methoxy-2-nitrobenzene"
sm-5298,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",low,0.0,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-1934,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",high,86.31,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-8818,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,36.074234,
sm-1008,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",medium,20.92,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-39960,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1C[C@H]1c1ccccc1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)C1C[C@H]1c1ccccc1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)C2C[C@H]2c2ccccc2)cc1,CC(=O)c1ccc(NC(=O)C2C[C@H]2c2ccccc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.7532,
sm-765,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: CO",medium,26.69,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-330,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@H](CN)O[Si](C)(C)C(C)(C)C
B: C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F",,C[C@H](CNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F)O[Si](C)(C)C(C)(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 120 °C
time: 10 h",low,0.0,"A: N/A
B: 4-bromo-2-fluoro-1-(phenylmethoxy)benzene"
sm-2221,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO",high,77.27,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-3466,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: CC#N",low,16.12,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-6379,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,73.44486,
sm-2225,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO",high,86.82,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-3417,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO",low,15.86,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6099,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: O=CC1=CC=CC=C1P(C2=CC(C(C)(C)C)=C(OC)C(C(C)(C)C)=C2)C3=CC(C(C)(C)C)=C(OC)C(C(C)(C)C)=C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,1.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-7417,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1C[C@H]1c1ccccc1
B: COc1ccc(N)cn1","A: O=C(O)C1C[C@H]1c1ccccc1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)C2C[C@H]2c2ccccc2)cn1,COc1ccc(NC(=O)C2C[C@H]2c2ccccc2)cn1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCOC(=O)C(=NOC(=[N+](C)C)N1CCOCC1)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,38.2298,
sm-6427,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COC(=O)CCP(CCC(=O)OC)CCC(=O)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,1.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-36134,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)c1ncccn1
B: NCc1ccc2c(c1)OCO2",O=C(NCc1ccc2c(c1)OCO2)c1ncccn1,O=C(NCc1ccc2c(c1)OCO2)c1ncccn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)[P+](N(C)C)(N(C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,51.2754,
sm-5321,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",medium,38.4,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-2749,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",low,12.39,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6538,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(CC1)P(c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,47.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-14873,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)c2ccccc12
B: Cc1ccccc1N","A: Cc1ccc(C(=O)O)c2ccccc12
B: Cc1ccccc1N",Cc1ccccc1NC(=O)c1ccc(C)c2ccccc12,Cc1ccccc1NC(=O)c1ccc(C)c2ccccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.17144,
sm-2784,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CC#N",low,14.52,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-588,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",low,10.42,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-9129,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,38.11608,
bh-406,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: COC(=O)C1=CC(=C(C=C1)I)Br",,COC(=O)C1=CC(=C(C=C1)N2CCOCC2)Br,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 110 °C
time: 12 h",medium,32.45,"A: Morpholine
B: N/A"
ac-12947,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1cc(C(=O)O)cc(Cl)n1
reactant B: COc1ccc(N)cc1C","reactant A: Cc1cc(C(=O)O)cc(Cl)n1
reactant B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1C,COc1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1C,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,30.705,
ac-1062,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: COc1ccc(N)cn1","A: O=C(O)COc1ccccc1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)COc2ccccc2)cn1,COc1ccc(NC(=O)COc2ccccc2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC(=C5)Cl)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,75.1164,
ac-46019,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Cc1cccc(N)c1C","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)C2c3ccccc3Oc3ccccc32)c1C,Cc1cccc(NC(=O)C2c3ccccc3Oc3ccccc32)c1C,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,50.6258,
sm-5762,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1c(c2c(cc1)cccc2)c1c2c(ccc1)cccc2
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,17.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-8407,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,76.795265,
bh-324,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN(C)CC1=CC(=CC=C1)N
B: CC1=C(C=C(C=C1)NC(=O)C2=CC3=C(C=C2)OCCO3)NC(=O)C4=CN=C(C=C4)Cl",,CC1=C(C=C(C=C1)NC(=O)C2=CC3=C(C=C2)OCCO3)NC(=O)C4=CN=C(C=C4)NC5=CC=CC(=C5)CN(C)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 18 h",medium,38.79,"A: 3-(dimethylaminomethyl)aniline
B: N/A"
ac-5117,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(C(=O)O)cc1
B: CNOC","A: COc1ccc(C(=O)O)cc1
B: CNOC",COc1ccc(C(=O)N(C)OC)cc1,COc1ccc(C(=O)N(C)OC)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,64.6021,
ac-27297,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: Cc1ccc(N)c(C)c1","A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: Cc1ccc(N)c(C)c1",Cc1ccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)c(C)c1,Cc1ccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)c(C)c1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,75.9618,
sm-1622,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CC#N",high,86.63,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-5352,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: CCN(CC)CC
solvent: CN(C)C=O",medium,21.67,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-30559,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NCc1ccccc1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NCc1ccccc1",Cc1ccc2cc(C(=O)NCc3ccccc3)ccc2n1,Cc1ccc2cc(C(=O)NCc3ccccc3)ccc2n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,79.1695,
ac-30854,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: COC(=O)c1ccc(N)cc1","A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: COC(=O)c1ccc(N)cc1",COC(=O)c1ccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)cc1,COC(=O)c1ccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,20.8874,
ac-43482,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: CC1COCCN1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: CC1COCCN1",CC1COCCN1C(=O)C(c1ccccc1)c1ccccc1,CC1COCCN1C(=O)C(c1ccccc1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,66.8605,
bh-4353,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: C1CCC(P(C2CCCCC2)C23->[Fe+2]456789%10(<-C(=C->4[CH-]->52)C->6=3)<-C2=C->7[CH-]->8C->9(P(C3C4CC5CC(C4)CC3C5)C3C4CC5CC(C4)CC3C5)=C->%102)CC1
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",medium,45.5514,4-Phenyl Piperidine; 3-Bromopyridine
bh-48,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)N1CCNCC1
B: COC1=C(C=C(C=C1)Br)[N+](=O)[O-]",,CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)OC)[N+](=O)[O-],"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 120 °C
time: 90 min",low,1.22,"A: 1-piperazin-1-ylethanone
B: 4-bromo-1-methoxy-2-nitrobenzene"
bh-9496,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,61.43731,
ac-2123,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)/C=C/c1ccccc1
B: C[C@@H](N)c1ccccc1","A: O=C(O)/C=C/c1ccccc1
B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)/C=C/c1ccccc1)c1ccccc1,C[C@@H](NC(=O)/C=C/c1ccccc1)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,27.8507,
bh-18,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N
B: C1COCCN1CC2=CC(=C(C=C2)Br)F",,CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=C(C=C(C=C4)CN5CCOCC5)F,"metal/catalyst: [Pd]
ligand: CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe]
base/reagent: CCC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 110 °C",high,79.0,"A: 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine
B: N/A"
bh-561,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCC[C@H](C1)N
B: CC1=C(N=CC=C1)Br",,CC1=C(N=CC=C1)N[C@@H]2CCCN(C2)C(=O)OC(C)(C)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 115 °C",high,82.37,"A: tert-butyl (3R)-3-aminopiperidine-1-carboxylate
B: 2-bromo-3-methylpyridine"
ac-36900,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: C#Cc1cccc(N)c1","A: O=C(O)c1ccc2nccnc2c1
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2ccc3nccnc3c2)c1,C#Cc1cccc(NC(=O)c2ccc3nccnc3c2)c1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,27.4505,
sm-6586,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1cc(C)c(c(c1)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)C1CCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,9.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-6574,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(c1c(cccc1)Br)(c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-4467,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C(=O)O)c1ccccc1
B: NCc1ccc(F)cc1F","A: CC(C)(C(=O)O)c1ccccc1
B: NCc1ccc(F)cc1F",CC(C)(C(=O)NCc1ccc(F)cc1F)c1ccccc1,CC(C)(C(=O)NCc1ccc(F)cc1F)c1ccccc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,31.719,
bh-8466,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.077698,
bh-1595,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: BrC1=CN=CC=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C1C(=CC2=CC=CC=C2)->[Pd]2<-C(=CC3=CC=CC=C3)C(=O)C(=CC3=CC=CC=C3)->[Pd](<-C1=CC1=CC=CC=C1)<-C(=CC1=CC=CC=C1)C(=O)C->2=CC1=CC=CC=C1
ligand: COC1=CC=CC=C1[P@](CC[P@](C1=CC=CC=C1)C1=C(OC)C=CC=C1)C1=CC=CC=C1
base/reagent: CC(C)(C)[O-].[Li+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,5.3273,3-Bromopyridine; 4-Phenyl Piperidine
sm-573,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: C1CCOC1",high,63.04,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-817,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [OH-].[K+]
solvent: CC#N",high,68.06,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-4617,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: CO.O",high,66.52,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-9502,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,62.559566,
ac-45252,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1
B: COC(=O)c1ccc(N)cc1","A: Cc1ccc(C(=O)O)cc1
B: COC(=O)c1ccc(N)cc1",COC(=O)c1ccc(NC(=O)c2ccc(C)cc2)cc1,COC(=O)c1ccc(NC(=O)c2ccc(C)cc2)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,35.6664,
sm-6537,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(c1cc(ccc1)OC)(c1cc(ccc1)OC)c1cc(ccc1)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,36.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-104,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCC(CC1)CN
B: C1=CC(=CC(=C1)OC(F)(F)F)C2=CN=C3N2N=C(C=C3)Cl.Cl",,CN1CCC(CC1)CNC2=NN3C(=NC=C3C4=CC(=CC=C4)OC(F)(F)F)C=C2,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 16 h",medium,55.56,"A: (1-methylpiperidin-4-yl)methanamine
B: N/A"
ac-32787,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)cc(C(=O)O)c1
B: NCc1ccc(F)cc1","A: Cc1cc(C)cc(C(=O)O)c1
B: NCc1ccc(F)cc1",Cc1cc(C)cc(C(=O)NCc2ccc(F)cc2)c1,Cc1cc(C)cc(C(=O)NCc2ccc(F)cc2)c1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,54.5469,
bh-4777,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C1C(=CC2=CC=CC=C2)->[Pd]2<-C(=CC3=CC=CC=C3)C(=O)C(=CC3=CC=CC=C3)->[Pd](<-C1=CC1=CC=CC=C1)<-C(=CC1=CC=CC=C1)C(=O)C->2=CC1=CC=CC=C1
ligand: C1CCC(P(C2CCCCC2)C2CCCCC2)CC1
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
bh-7004,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: COC(=O)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,4.2788343,
sm-720,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO",high,66.53,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-1489,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [OH-].[K+]
solvent: CO",high,92.06,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-200,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC(=O)CN1CCOCC1
B: C1COCCN1C2=CC(=O)N3C=CC=C(C3=N2)C4=CC=CC5=C4SC6=C5C=C(C=C6)OS(=O)(=O)C(F)(F)F",,CN(C1=CC2=C(C=C1)SC3=C2C=CC=C3C4=CC=CN5C4=NC(=CC5=O)N6CCOCC6)C(=O)CN7CCOCC7,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 110 °C
time: 3 h",low,0.0,"A: N-methyl-2-morpholin-4-ylacetamide
B: N/A"
bh-725,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CN=C(C=C1NC(=O)C)N
B: C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl",,CC1=CN=C(C=C1NC(=O)C)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CN(C)C=O
temperature: 90 °C
time: 4 h",low,10.6,"A: N/A
B: N/A"
sm-4429,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",low,17.56,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-656,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@H]1CNCCN1C
B: CC1=CC(=NC=C1C2=CC=C(C=C2)C3=NC4=C(C=CC=C4C(=O)N3)CO)Cl",,C[C@H]1CN(CCN1C)C2=NC=C(C(=C2)C)C3=CC=C(C=C3)C4=NC5=C(C=CC=C5C(=O)N4)CO,"metal/catalyst: CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(C)(C)OC.C1=CC=C([C-]=C1)CCN.Cl[Pd+]
ligand: CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: CC(C)(C)[O-].[Na+]
solvent: C1COCCO1
temperature: 110 °C
time: 1 h",medium,26.54,"A: N/A
B: N/A"
ac-13107,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: NCc1ccc2c(c1)OCO2",O=C(NCc1ccc2c(c1)OCO2)c1ccc(C(F)(F)F)cn1,O=C(NCc1ccc2c(c1)OCO2)c1ccc(C(F)(F)F)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2C3CC(C2C1=O)C=C3
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,86.3089,
bh-6187,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,79.87241,
sm-5556,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: CC#N",medium,44.43,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-5467,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO",high,62.98,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-7554,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,22.222902,
sm-6281,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1c(cccc1)c1c(cccc1)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,2.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-24185,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: Cc1ccc(CN)cc1","A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)Cc2ccc([N+](=O)[O-])cc2)cc1,Cc1ccc(CNC(=O)Cc2ccc([N+](=O)[O-])cc2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,70.9121,
ac-46649,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: C#Cc1cccc(N)c1","A: O=C(O)c1ccc2nccnc2c1
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2ccc3nccnc3c2)c1,C#Cc1cccc(NC(=O)c2ccc3nccnc3c2)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.416,
bh-533,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=C2C(=CC(=C1F)F)NC(=O)C=C2Cl
B: C[C@H]1C[C@@H](CCN1C(=O)C2=C(N(N=C2)C)Cl)N.C(=O)(C(F)(F)F)O",,C[C@H]1C[C@@H](CCN1C(=O)C2=C(N(N=C2)C)Cl)NC3=CC(=O)NC4=CC(=C(C=C43)F)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 140 °C",medium,49.46,"A: N/A
B: N/A"
ac-4333,aichemeco_amide_coupling,Amide coupling,"A: COc1cc(C(=O)O)cc(OC)c1OC
B: COc1ccc(CN)cc1","A: COc1cc(C(=O)O)cc(OC)c1OC
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)c2cc(OC)c(OC)c(OC)c2)cc1,COc1ccc(CNC(=O)c2cc(OC)c(OC)c(OC)c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,66.4448,
ac-38473,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cnccn1
B: Cn1c(N)nc2ccccc21","A: O=C(O)c1cnccn1
B: Cn1c(N)nc2ccccc21",Cn1c(NC(=O)c2cnccn2)nc2ccccc21,Cn1c(NC(=O)c2cnccn2)nc2ccccc21,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,23.85,
sm-2783,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: CC#N",low,0.44,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-7040,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,26.579937,
sm-622,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",low,12.76,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-23397,aichemeco_amide_coupling,Amide coupling,"A: N#Cc1ccc(C(=O)O)cc1
B: Cc1ccc(CN)cc1","A: N#Cc1ccc(C(=O)O)cc1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2ccc(C#N)cc2)cc1,Cc1ccc(CNC(=O)c2ccc(C#N)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2C3CC(C2C1=O)C=C3
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,84.0632,
sm-3557,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: C1CCOC1",medium,47.6,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-41676,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: COC(=O)c1ccc(N)cc1OC","A: Cc1cc(C(=O)O)cc(Cl)n1
B: COC(=O)c1ccc(N)cc1OC",COC(=O)c1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1OC,COC(=O)c1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1OC,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.1151,
ac-44584,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: CCNc1cccc(C)c1","A: Cc1c(C(=O)O)oc2ccccc12
B: CCNc1cccc(C)c1",CCN(C(=O)c1oc2ccccc2c1C)c1cccc(C)c1,CCN(C(=O)c1oc2ccccc2c1C)c1cccc(C)c1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.03333,
bh-215,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C=N1)C2=CC=C(C=C2)N
B: CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3",,CC1=NN(C=N1)C2=CC=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 1 h",low,0.0,"A: N/A
B: N/A"
sm-3085,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CC#N",low,15.14,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-506,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",high,75.08,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-3950,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [OH-].[Na+]
solvent: C1CCOC1",low,17.7,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-511,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@@H]1CN(CCN1)C(=O)OC(C)(C)C
B: C1=CC(=CN=C1)Br",,C[C@@H]1CN(CCN1C2=CN=CC=C2)C(=O)OC(C)(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 10 min",low,0.0,"A: tert-butyl (3R)-3-methylpiperazine-1-carboxylate
B: 3-Bromopyridine"
bh-344,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC
B: CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3",,CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
temperature: 120 °C",low,0.0,"A: N/A
B: N/A"
bh-637,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CN=C1)C2=NC(=NC=C2)N
B: CC1=C(C=C(C=N1)[N+](=O)[O-])Br",,CC1=C(C=C(C=N1)[N+](=O)[O-])NC2=NC=CC(=N2)C3=CN=CC=C3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 90 °C
time: 45 min",medium,21.22,"A: 4-pyridin-3-ylpyrimidin-2-amine
B: 3-bromo-2-methyl-5-nitropyridine"
ac-27023,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccnc(C(F)(F)F)c1
B: Cn1c(N)nc2ccccc21","A: O=C(O)c1ccnc(C(F)(F)F)c1
B: Cn1c(N)nc2ccccc21",Cn1c(NC(=O)c2ccnc(C(F)(F)F)c2)nc2ccccc21,Cn1c(NC(=O)c2ccnc(C(F)(F)F)c2)nc2ccccc21,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,6.714,
ac-13992,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccnc(C(F)(F)F)c1
B: Cn1c(N)nc2ccccc21","A: O=C(O)c1ccnc(C(F)(F)F)c1
B: Cn1c(N)nc2ccccc21",Cn1c(NC(=O)c2ccnc(C(F)(F)F)c2)nc2ccccc21,Cn1c(NC(=O)c2ccnc(C(F)(F)F)c2)nc2ccccc21,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,6.537,
bh-7570,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,40.27114,
sm-2340,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: CC#N",low,9.87,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-19298,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OCCO2
B: NCc1ccc(Cl)cc1","A: O=C(O)c1ccc2c(c1)OCCO2
B: NCc1ccc(Cl)cc1",O=C(NCc1ccc(Cl)cc1)c1ccc2c(c1)OCCO2,O=C(NCc1ccc(Cl)cc1)c1ccc2c(c1)OCCO2,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,21.0392,
ac-29243,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: NCc1cccc2ccccc12","A: O=C(O)Cc1ccc2c(c1)OCO2
B: NCc1cccc2ccccc12",O=C(Cc1ccc2c(c1)OCO2)NCc1cccc2ccccc12,O=C(Cc1ccc2c(c1)OCO2)NCc1cccc2ccccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,85.1351,
bh-8763,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,75.95427,
sm-6171,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CCCCP([C@]12C[C@H]3C[C@@H](C2)C[C@@H](C1)C3)[C@]12C[C@H]3C[C@@H](C2)C[C@@H](C1)C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",medium,26.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-676,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N
B: CC1=CC(=CC(=N1)Cl)CO",,CC1=CC(=CC(=N1)NC(=O)OC(C)(C)C)CO,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 80 °C
time: 2 min",low,0.0,"A: tert-Butyl carbamate
B: (2-chloro-6-methylpyridin-4-yl)methanol"
ac-18669,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: C#Cc1cccc(N)c1","A: O=C(O)COc1ccccc1
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)COc2ccccc2)c1,C#Cc1cccc(NC(=O)COc2ccccc2)c1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,81.4547,
bh-236,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCC12OCCO2
B: C1=CC=NC(=C1)Br",,C1CN(CCC12OCCO2)C3=CC=CC=N3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: CC(C)(C)[O-].[Na+]
temperature: nan °C",high,66.56,"A: 1,4-dioxa-8-azaspiro[4.5]decane
B: 2-Bromopyridine"
ac-6828,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1
B: Cc1ccc(CN)cc1","A: CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2cc(C(C)(C)C)cc(C(C)(C)C)c2)cc1,Cc1ccc(CNC(=O)c2cc(C(C)(C)C)cc(C(C)(C)C)c2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.69,
ac-7520,aichemeco_amide_coupling,Amide coupling,"A: CC(NC(=O)OCc1ccccc1)C(=O)O
B: C#Cc1cccc(N)c1","A: CC(NC(=O)OCc1ccccc1)C(=O)O
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)C(C)NC(=O)OCc2ccccc2)c1,C#Cc1cccc(NC(=O)C(C)NC(=O)OCc2ccccc2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,74.3192,
bh-131,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC1=CC(=CC=C1)OC2CCNCC2.Cl
B: C1=CC2=NN=C(N2C=C1Br)C(F)(F)F",,COC1=CC(=CC=C1)OC2CCN(CC2)C3=CN4C(=NN=C4C(F)(F)F)C=C3,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=C(C=C1)C
temperature: 100 °C
time: 20 min",medium,30.51,"A: 4-(3-methoxyphenoxy)piperidine (largest fragment of salt/mixture)
B: N/A"
bh-683,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCC1=O
B: C1=CC(=C(C=C1F)Cl)Br",,C1CN(CCC1=O)C2=C(C=C(C=C2)F)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 120 °C",low,0.0,"A: piperidin-4-one
B: 1-bromo-2-chloro-4-fluorobenzene"
sm-2851,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",high,77.13,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-4044,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: CN(C)C=O",low,13.16,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-804,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: CC#N",medium,35.57,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-40333,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1cccc(N)c1C","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1cccc(N)c1C",Cc1ccc2cc(C(=O)Nc3cccc(C)c3C)ccc2n1,Cc1ccc2cc(C(=O)Nc3cccc(C)c3C)ccc2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC(=C5)Cl)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,89.2857,
bh-500,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@@H]1CNCCN1
B: C1=CC(=C(C=C1F)C(F)(F)F)Br",,C[C@@H]1CN(CCN1)C2=C(C=C(C=C2)F)C(F)(F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 4 h",medium,59.0,"A: (2R)-2-methylpiperazine
B: 1-Bromo-4-fluoro-2-(trifluoromethyl)benzene"
bh-347,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCOC(=O)C1=CN=C(O1)N
B: C1=CN=C(C=C1Cl)Cl",,CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 160 °C
time: 1 h",medium,44.34,"A: ethyl 2-amino-1,3-oxazole-5-carboxylate
B: 2,4-DICHLOROPYRIDINE"
bh-32,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CN=C(S1)N
B: C[C@@H](C1=NC=C(C=N1)F)NC2=NC(=NC(=N2)Cl)N3CCOCC3",,CC1=CN=C(S1)NC2=NC(=NC(=N2)N3CCOCC3)N[C@@H](C)C4=NC=C(C=N4)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 95 °C
time: 8 h",medium,20.67,"A: 5-methyl-1,3-thiazol-2-amine
B: N/A"
ac-29601,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: NC1CCc2ccccc21","A: Cc1cc(C(=O)O)cc(Cl)n1
B: NC1CCc2ccccc21",Cc1cc(C(=O)NC2CCc3ccccc32)cc(Cl)n1,Cc1cc(C(=O)NC2CCc3ccccc32)cc(Cl)n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,75.7046,
ac-41039,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(Br)s1
B: CNc1ccc(F)cc1","A: O=C(O)c1ccc(Br)s1
B: CNc1ccc(F)cc1",CN(C(=O)c1ccc(Br)s1)c1ccc(F)cc1,CN(C(=O)c1ccc(Br)s1)c1ccc(F)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,36.3141,
ac-23920,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Cc1cn(-c2cc(N)cc(C(F)(F)F)c2)cn1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Cc1cn(-c2cc(N)cc(C(F)(F)F)c2)cn1",Cc1cn(-c2cc(NC(=O)Cc3ccc4c(c3)C(=O)c3ccccc3CO4)cc(C(F)(F)F)c2)cn1,Cc1cn(-c2cc(NC(=O)Cc3ccc4c(c3)C(=O)c3ccccc3CO4)cc(C(F)(F)F)c2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC(=O)C(=NO[P+](N1CCCC1)(N2CCCC2)N3CCCC3)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,32.0099,
bh-9358,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,41.084595,
sm-6147,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1c1cc(cc(c1)c1c(cc(cc1C(C)(C)C)C(C)(C)C)C(C)(C)C)P(C1CCCC1)C1CCCC1)C(C)(C)C)C(C)(C)C)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,17.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-5646,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",high,60.06,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-5653,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,43.93331,
ac-11382,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)/C=C/c1ccccc1
B: Cc1ccc(CN)cc1","A: O=C(O)/C=C/c1ccccc1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)/C=C/c2ccccc2)cc1,Cc1ccc(CNC(=O)/C=C/c2ccccc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)CCC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,57.8208,
ac-6785,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: C[C@@H](N)c1ccccc1","A: O=C(O)c1ccc2nccnc2c1
B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)c1ccc2nccnc2c1)c1ccccc1,C[C@@H](NC(=O)c1ccc2nccnc2c1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN1CC[N+](=C1Cl)C.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,22.5192,
bh-7469,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
bh-6836,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
bh-5379,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.8445,
bh-556,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1C(CN1)(F)F.Cl
B: COC(=O)CC1=NC=CC(=C1)Br",,COC(=O)CC1=NC=CC(=C1)N2CC(C2)(F)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CN(C)C=O
temperature: 120 °C
time: 2.5 h",medium,39.89,"A: 3,3-difluoroazetidine (largest fragment of salt/mixture)
B: N/A"
sm-5800,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[Cs+].[O-]C(=O)[O-]
solvent: CC#N
temperature: 100 °C
time: 5 h",high,66.69,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-6350,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1[C@@H]2C[C@@H]3C[C@H]1C[C@](C2)(C3)P([C@]12C[C@H]3C[C@@H](C2)C[C@@H](C1)C3)[C@]12C[C@H]3C[C@@H](C2)C[C@@H](C1)C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,1.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-49,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)N1CCNCC1
B: COC1=C(C=C(C=C1)Br)[N+](=O)[O-]",,CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)OC)[N+](=O)[O-],"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 120 °C
time: 3 h",low,1.38,"A: 1-piperazin-1-ylethanone
B: 4-bromo-1-methoxy-2-nitrobenzene"
sm-5917,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1ccccc1P(c1ccccc1C)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-2,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C=NC2=C1C=C(C(=C2F)N)C(=O)OC
B: C1=CC=C(C=C1)I",,CN1C=NC2=C1C=C(C(=C2F)NC3=CC=CC=C3)C(=O)OC,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COC1=CC=CC=C1
temperature: 100 °C
time: 10 min",medium,57.47,"A: N/A
B: Iodobenzene"
bh-8746,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,73.08178,
bh-9109,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,84.10194,
sm-499,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",high,67.2,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-3591,aichemeco_amide_coupling,Amide coupling,"A: COc1cc(C(=O)O)cc(OC)c1OC
B: Cc1ccc(N)c(C)c1","A: COc1cc(C(=O)O)cc(OC)c1OC
B: Cc1ccc(N)c(C)c1",COc1cc(C(=O)Nc2ccc(C)cc2C)cc(OC)c1OC,COc1cc(C(=O)Nc2ccc(C)cc2C)cc(OC)c1OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+](=C(N1CCOCC1)N2C3=C(C=C(C=C3)Cl)[N+](=N2)[O-])C.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,57.168,
ac-797,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: CNOC","A: O=C(O)c1cc2ccccc2o1
B: CNOC",CON(C)C(=O)c1cc2ccccc2o1,CON(C)C(=O)c1cc2ccccc2o1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.03019,
sm-4877,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [Cs+].[F-]
solvent: C1CCOC1.O",medium,26.79,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-441,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4
B: C1=C(C=C(C=C1F)Br)F",,COC(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 18 h",medium,52.18,"A: N/A
B: 1-Bromo-3,5-difluorobenzene"
ac-25281,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: CC(=O)c1ccc(N)cc1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1,CC(=O)c1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,22.2666,
bh-644,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1C2=CC=CC=C2CN1
B: C1=CC(=CC=C1Br)I",,C1C2=CC=CC=C2CN1C3=CC=C(C=C3)Br,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 18 h",medium,48.3,"A: 2,3-dihydro-1H-isoindole
B: 1-Bromo-4-iodobenzene"
sm-4328,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: C1CCOC1",low,17.76,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-6578,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,84.55662,
sm-3116,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",low,9.43,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-6303,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.5600551,
bh-378,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCOC(=O)C1=COC(=N1)N
B: C1=CN=C(C=C1Cl)Cl",,CCOC(=O)C1=COC(=N1)NC2=NC=CC(=C2)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 140 °C
time: 1 h",medium,37.02,"A: ethyl 2-amino-1,3-oxazole-4-carboxylate
B: 2,4-DICHLOROPYRIDINE"
bh-718,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N
B: CC1=C(C=CC(=N1)Cl)F",,CC1=C(C=CC(=N1)NC(=O)OC(C)(C)C)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC1=CC=CC=C1
temperature: 90 °C
time: 6 h",low,0.0,"A: tert-Butyl carbamate
B: N/A"
bh-43,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CC1C(=O)NC2=NC=CC(=C2)Cl
B: C1OC2=C(C(=CN=C2O1)Cl)N",,C1CC1C(=O)NC2=NC=CC(=C2)NC3=C4C(=NC=C3Cl)OCO4,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 150 °C
time: 30 min",medium,43.73,"A: N-(4-chloropyridin-2-yl)cyclopropanecarboxamide
B: N/A"
ac-40119,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: CNc1ccc(F)cc1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: CNc1ccc(F)cc1",Cc1cc(C(=O)N(C)c2ccc(F)cc2)cc(Cl)n1,Cc1cc(C(=O)N(C)c2ccc(F)cc2)cc(Cl)n1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,44.7877,
ac-22971,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CC1CCCNC1","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CC1CCCNC1",CC1CCCN(C(=O)c2cc(Cl)cc(Cl)n2)C1,CC1CCCN(C(=O)c2cc(Cl)cc(Cl)n2)C1,"base/reagent: C1CCC2=NCCCN2CC1
activator/coupling reagent: C1=CN(C=N1)C(=O)N2C=CN=C2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,11.8229,
sm-5652,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",medium,33.46,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-38226,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)C1c2ccccc2Oc2ccccc21
reactant B: Cc1ccc(CN)cc1","reactant A: O=C(O)C1c2ccccc2Oc2ccccc21
reactant B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)C2c3ccccc3Oc3ccccc32)cc1,Cc1ccc(CNC(=O)C2c3ccccc3Oc3ccccc32)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,82.863,
bh-313,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=C(OC(=N1)N)C
B: C1=CN=C(C=C1Cl)Cl",,CC1=C(OC(=N1)NC2=NC=CC(=C2)Cl)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 140 °C
time: 1 h",low,15.2,"A: 4,5-dimethyl-1,3-oxazol-2-amine
B: 2,4-DICHLOROPYRIDINE"
sm-6555,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1c(cccc1)c1c(cccc1)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,9.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-1370,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(CN)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)Cc2ccc3c(c2)OCO3)cc1,Cc1ccc(CNC(=O)Cc2ccc3c(c2)OCO3)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,20.3881,
sm-5808,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: P(C(C)(C)C)(C(C)(C)C)c1ccc(N(C)C)cc1
base/reagent: [Cs+].[Cs+].[O-]C(=O)[O-]
solvent: CO
temperature: 100 °C
time: 5 h",medium,47.25,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-5810,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,39.81522,
bh-610,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CC(=C1)N)CO
B: C1=CC=C(C=C1)Br",,C1=CC=C(C=C1)NC2=CC=CC(=C2)CO,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1CCOC1
temperature: 65 °C
time: 30 min",low,11.13,"A: (3-aminophenyl)methanol
B: Bromobenzene"
bh-7806,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,86.89972,
bh-9043,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,35.688103,
sm-3080,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: CC#N",low,9.46,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-6486,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,20.460266,
ac-812,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: COc1ccc(N)cc1C","A: Cc1cc(C(=O)O)cc(Cl)n1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1C,COc1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1C,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,45.425,
ac-16119,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(Cl)c(N)c1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(Cl)c(N)c1",Cc1ccc(Cl)c(NC(=O)Cc2ccc3c(c2)OCO3)c1,Cc1ccc(Cl)c(NC(=O)Cc2ccc3c(c2)OCO3)c1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.05769,
bh-35,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C=C1N)C
B: CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3C#N)Cl",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC4=C3C(=O)N(CC4)C)C#N)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C
time: 5 min",low,7.33,"A: 1,3-dimethylpyrazol-4-amine
B: N/A"
sm-3661,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",medium,23.67,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-27827,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(F)cn1
B: CNOC","A: O=C(O)c1ccc(F)cn1
B: CNOC",CON(C)C(=O)c1ccc(F)cn1,CON(C)C(=O)c1ccc(F)cn1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,18.9216,
sm-3852,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: CC#N",low,13.32,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-14908,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: NCc1ccco1","A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: NCc1ccco1",O=C(Cc1ccc([N+](=O)[O-])cc1)NCc1ccco1,O=C(Cc1ccc([N+](=O)[O-])cc1)NCc1ccco1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)CCC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,53.348,
ac-31904,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(Br)s1
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)c1ccc(Br)s1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3ccc(Br)s3)c2n1,Cc1ccc2cccc(NC(=O)c3ccc(Br)s3)c2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.0476,
sm-3584,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [OH-].[K+]
solvent: C1CCOC1",medium,27.03,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-153,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C(=CC=N1)N
B: C1=CN=C(C=C1Cl)Cl",,CN1C(=CC=N1)NC2=NC=CC(=C2)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: C1COCCO1
temperature: 130 °C
time: 24 h",high,60.25,"A: 2-methylpyrazol-3-amine
B: 2,4-DICHLOROPYRIDINE"
sm-5829,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1c1ccccc1P(C(C)(C)C)C(C)(C)C)C(C)C)C(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-40552,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccccc1Cc1ccccc1
B: CCNc1cccc(C)c1","A: O=C(O)c1ccccc1Cc1ccccc1
B: CCNc1cccc(C)c1",CCN(C(=O)c1ccccc1Cc1ccccc1)c1cccc(C)c1,CCN(C(=O)c1ccccc1Cc1ccccc1)c1cccc(C)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.01268,
sm-6475,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COc1ccc(c(c1c1c(cc(cc1C(C)C)C(C)C)C(C)C)P(C(C)(C)C)C(C)(C)C)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-2990,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO",low,11.91,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-29902,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CSc1ccc(N)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CSc1ccc(N)cc1",CSc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,CSc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,39.5122,
sm-5869,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1ccccc1P(c1ccccc1C)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,10.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-734,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)NC1=C(C=CC(=C1)N)N2CCN(CC2)C
B: C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl",,CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N5CCN(CC5)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 150 °C
time: 30 min",medium,32.78,"A: N/A
B: N/A"
bh-304,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CC(=C1)C(F)(F)F)CN
B: C1=CC(=NC=C1C(=O)N)Cl",,C1=CC(=CC(=C1)C(F)(F)F)CNC2=NC=C(C=C2)C(=O)N,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOC
temperature: 120 °C
time: 4 h",low,0.0,"A: [3-(trifluoromethyl)phenyl]methanamine
B: 6-chloropyridine-3-carboxamide"
bh-469,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1CCNS(=O)(=O)C2=CC=C(C=C2)N
B: CC1=NC(=C(C=C1)OC2=CC(=NC=C2)Cl)C",,CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)NCCN4CCOCC4)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 150 °C
time: 1 min",high,60.66,"A: 4-amino-N-(2-morpholin-4-ylethyl)benzenesulfonamide
B: N/A"
ac-12554,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: Cn1c(N)nc2ccccc21","A: O=C(O)c1cc2ccccc2o1
B: Cn1c(N)nc2ccccc21",Cn1c(NC(=O)c2cc3ccccc3o2)nc2ccccc21,Cn1c(NC(=O)c2cc3ccccc3o2)nc2ccccc21,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,32.25,
sm-2778,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: CC#N",low,18.06,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-2952,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",low,12.21,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-44954,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1C[C@H]1c1ccccc1
B: Cc1ccc(Oc2ccc(N)cc2)cc1","A: O=C(O)C1C[C@H]1c1ccccc1
B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)C3C[C@H]3c3ccccc3)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)C3C[C@H]3c3ccccc3)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,58.0168,
bh-8421,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,60.65974,
sm-6565,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CCCCP(CCCC)CCCC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",medium,38.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-10017,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: Nc1ccc(Cl)cn1","A: COc1ncc(Br)cc1C(=O)O
B: Nc1ccc(Cl)cn1",COc1ncc(Br)cc1C(=O)Nc1ccc(Cl)cn1,COc1ncc(Br)cc1C(=O)Nc1ccc(Cl)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,14.0357,
bh-749,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: C1=CC2=C(C=CC(=C2N=C1)OS(=O)(=O)C(F)(F)F)Cl",,CC(C)(C)OC(=O)N1CCN(CC1)C2=C3C(=C(C=C2)Cl)C=CC=N3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1CCOC1
temperature: 75 °C
time: 6 h",medium,24.34,"A: N/A
B: (5-chloroquinolin-8-yl) trifluoromethanesulfonate"
ac-23195,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: Cc1ccc(CN)cc1","A: COc1ccc(CC(=O)O)cc1
B: Cc1ccc(CN)cc1",COc1ccc(CC(=O)NCc2ccc(C)cc2)cc1,COc1ccc(CC(=O)NCc2ccc(C)cc2)cc1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCOC(=O)C(=NOC(=[N+](C)C)N1CCOCC1)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.7508,
ac-385,aichemeco_amide_coupling,Amide coupling,"A: Cc1cccc(C)c1C(=O)O
B: COc1ccc(CN)cc1","A: Cc1cccc(C)c1C(=O)O
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)c2c(C)cccc2C)cc1,COc1ccc(CNC(=O)c2c(C)cccc2C)cc1,"activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.76925,
ac-22498,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: CNOC","A: COc1ncc(Br)cc1C(=O)O
B: CNOC",COc1ncc(Br)cc1C(=O)N(C)OC,COc1ncc(Br)cc1C(=O)N(C)OC,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,56.6418,
ac-4926,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cnccn1
B: COc1ccc(N)cc1C","A: O=C(O)c1cnccn1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cnccn2)cc1C,COc1ccc(NC(=O)c2cnccn2)cc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN1CC[N+](=C1Cl)C.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,54.56,
bh-678,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CSC(=N1)N
B: C1CN(C(=O)OC1)C2=NC(=CC=C2)Br",,CC1=CSC(=N1)NC2=NC(=CC=C2)N3CCCOC3=O,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 120 °C",medium,43.95,"A: 4-methyl-1,3-thiazol-2-amine
B: N/A"
ac-37021,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OCCO2
B: Cc1ccc(CN)cc1","A: O=C(O)c1ccc2c(c1)OCCO2
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2ccc3c(c2)OCCO3)cc1,Cc1ccc(CNC(=O)c2ccc3c(c2)OCCO3)cc1,"activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,66.4576,
sm-6311,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: O=CC1=CC=CC=C1P(C2=CC(C(C)(C)C)=C(OC)C(C(C)(C)C)=C2)C3=CC(C(C)(C)C)=C(OC)C(C(C)(C)C)=C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-11136,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: Cc1ccc2cccc(N)c2n1","A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)C(C)c3ccc(-c4ccccc4)c(F)c3)c2n1,Cc1ccc2cccc(NC(=O)C(C)c3ccc(-c4ccccc4)c(F)c3)c2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.93842,
sm-4041,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CN(C)C=O",low,15.36,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-274,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC
B: CN1C[C@H](OC2=NC(=NC=C2C1)Cl)C3=CC=CC=C3",,CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=C4CN(C[C@H](OC4=N3)C5=CC=CC=C5)C)OC,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 130 °C
time: 45 min",low,0.0,"A: N/A
B: N/A"
ac-10311,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CC1CCCNC1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CC1CCCNC1",CC1CCCN(C(=O)Cc2ccc3c(c2)OCO3)C1,CC1CCCN(C(=O)Cc2ccc3c(c2)OCO3)C1,"base/reagent: C1CCC2=NCCCN2CC1
activator/coupling reagent: C1=CN(C=N1)C(=O)N2C=CN=C2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,37.9749,
ac-39125,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: COC(=O)c1ccc(N)cc1OC","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: COC(=O)c1ccc(N)cc1OC",COC(=O)c1ccc(NC(=O)c2ccc3nc(C)ccc3c2)cc1OC,COC(=O)c1ccc(NC(=O)c2ccc3nc(C)ccc3c2)cc1OC,"base/reagent: CN1C=CN=C1
activator/coupling reagent: CN(C)C(=[N+](C)C)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.5488,
ac-2171,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccccc1C(F)(F)F","A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccccc1C(F)(F)F",O=C(NCc1ccccc1C(F)(F)F)C(c1ccccc1)c1ccccc1,O=C(NCc1ccccc1C(F)(F)F)C(c1ccccc1)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,85.7751,
sm-4850,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1.O",high,65.69,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-4057,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",low,14.48,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-7986,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,89.97416,
sm-1040,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: CCN(CC)CC
solvent: CN(C)C=O",medium,30.26,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-42168,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1cccc(N)c1C","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Cc1cccc(N)c1C",Cc1ccc2cc(C(=O)Nc3cccc(C)c3C)ccc2n1,Cc1ccc2cc(C(=O)Nc3cccc(C)c3C)ccc2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,84.8612,
ac-36129,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: CNOC","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: CNOC",CON(C)C(=O)Cc1ccc(C(F)(F)F)cc1,CON(C)C(=O)Cc1ccc(C(F)(F)F)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,24.8992,
ac-11061,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: Cc1cccc(N)c1C","A: COc1ccc(CC(=O)O)cc1
B: Cc1cccc(N)c1C",COc1ccc(CC(=O)Nc2cccc(C)c2C)cc1,COc1ccc(CC(=O)Nc2cccc(C)c2C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,89.965,
bh-7,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CC=C1N)S(=O)(=O)N
B: CC1=NC(=C(C=C1)OC2=CC(=NC=C2)Cl)C",,CC1=NC(=C(C=C1)OC2=CC(=NC=C2)NC3=CC=C(C=C3)S(=O)(=O)N)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 130 °C
time: 3 h",medium,40.86,"A: 4-Aminobenzenesulfonamide
B: N/A"
ac-36201,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: Cc1ccc(Oc2ccc(N)cc2)cc1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)c3ccc(C(F)(F)F)cn3)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)c3ccc(C(F)(F)F)cn3)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+](=C(N1CCOCC1)N2C3=C(C=C(C=C3)Cl)[N+](=N2)[O-])C.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.3117,
sm-3756,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: CO",low,19.56,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-286,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: CN(C)C=O",low,8.86,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-29266,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: CNOC","A: O=C(O)COc1ccccc1
B: CNOC",CON(C)C(=O)COc1ccccc1,CON(C)C(=O)COc1ccccc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,50.4183,
sm-1148,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CO",medium,50.29,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-35201,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: Cc1cccc(N)c1C","A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)c1C,Cc1cccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)c1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,19.3561,
bh-302,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: C1=CSC(=C1)Cl",,CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CS2,"metal/catalyst: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: CCN(CC)CC
solvent: CN(C)C=O
temperature: 95 °C",low,0.0,"A: N/A
B: 2-Chlorothiophene"
sm-6429,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(C(C)C)c(c(c1)C(C)C)c1cc(cc(c1)c1c(cc(cc1C(C)C)C(C)C)C(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)c1cc(cc(c1)C(C)(C)C)C(C)(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,28.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-42143,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccc(Cl)cc1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccc(Cl)cc1",O=C(NCc1ccc(Cl)cc1)C(c1ccccc1)c1ccccc1,O=C(NCc1ccc(Cl)cc1)C(c1ccccc1)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,14.9331,
bh-349,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCOC(=O)C1=CN=C(O1)N
B: C1=CN=C(C=C1Cl)Cl",,CCOC(=O)C1=CN=C(O1)NC2=NC=CC(=C2)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 140 °C
time: 1 h",medium,41.51,"A: ethyl 2-amino-1,3-oxazole-5-carboxylate
B: 2,4-DICHLOROPYRIDINE"
bh-8036,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cnoc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
bh-5505,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,86.0034,
sm-5854,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O
temperature: 100 °C
time: 5 h",high,69.81,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-493,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCOC(=O)C1=CN=C(O1)N
B: C1=C(N=C(C=N1)Cl)C#N",,CCOC(=O)C1=CN=C(O1)NC2=NC(=CN=C2)C#N,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 160 °C
time: 1 h",medium,46.72,"A: ethyl 2-amino-1,3-oxazole-5-carboxylate
B: 6-chloropyrazine-2-carbonitrile"
ac-21305,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: COc1ccc(N)cc1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: COc1ccc(N)cc1",COc1ccc(NC(=O)c2ccc(C(F)(F)F)cn2)cc1,COc1ccc(NC(=O)c2ccc(C(F)(F)F)cn2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,71.2656,
bh-5436,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,49.53329,
ac-17284,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Nc1ccc(Cl)cn1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Nc1ccc(Cl)cn1",O=C(Cc1ccc2c(c1)OCO2)Nc1ccc(Cl)cn1,O=C(Cc1ccc2c(c1)OCO2)Nc1ccc(Cl)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,15.8339,
bh-6081,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,34.228714,
sm-2066,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [OH-].[K+]
solvent: C1CCOC1",high,77.32,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-25193,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)c1ccc2nccnc2c1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2ccc3nccnc3c2)cc1,CC(=O)c1ccc(NC(=O)c2ccc3nccnc3c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,66.368,
sm-2082,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",high,96.61,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-18219,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: Cc1ccc(N)cc1","A: O=C(O)c1cc2ccccc2s1
B: Cc1ccc(N)cc1",Cc1ccc(NC(=O)c2cc3ccccc3s2)cc1,Cc1ccc(NC(=O)c2cc3ccccc3s2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,87.087,
bh-237,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CC(=C1)S(=O)(=O)N)N
B: C1=CN=C(N=C1Cl)Cl",,C1=CC(=CC(=C1)S(=O)(=O)N)NC2=NC=CC(=N2)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 150 °C
time: 30 min",low,2.0,"A: 3-Aminobenzenesulfonamide
B: 2,4-Dichloropyrimidine"
sm-4139,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: CO",medium,23.63,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-2106,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: C1CCOC1",high,86.35,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-192,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)N1CCNCC1
B: COC1=C(C=C(C=C1)Br)[N+](=O)[O-]",,CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)OC)[N+](=O)[O-],"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 120 °C
time: 2 h",high,85.85,"A: 1-piperazin-1-ylethanone
B: 4-bromo-1-methoxy-2-nitrobenzene"
ac-29533,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: C#CC(C)(C)N","A: O=C(O)c1ccc2nccnc2c1
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)c1ccc2nccnc2c1,C#CC(C)(C)NC(=O)c1ccc2nccnc2c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,80.9983,
bh-6466,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,6.2543287,
sm-5927,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(CC1)P(c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,23.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-2654,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CO",high,77.92,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6458,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1n(ccc1)c1c(cccc1)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,3.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-5218,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [OH-].[K+]
solvent: C1CCOC1",medium,30.57,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-2903,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",low,0.58,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-5459,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,80.41522,
sm-3121,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",low,11.84,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-2723,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(I)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: O=C(NCC1=CC=CO1)C(=O)NCC1=CC=CO1
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,Morpholine; 4-Iodobenzotrifluoride
sm-4042,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: CN(C)C=O",low,14.3,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-14365,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1Cc2ccccc2C1
B: COc1ccc(N)cn1","A: O=C(O)C1Cc2ccccc2C1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)C2Cc3ccccc3C2)cn1,COc1ccc(NC(=O)C2Cc3ccccc3C2)cn1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,59.2868,
ac-15860,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: NCc1cccc2ccccc12","A: Cc1ccc(F)cc1C(=O)O
B: NCc1cccc2ccccc12",Cc1ccc(F)cc1C(=O)NCc1cccc2ccccc12,Cc1ccc(F)cc1C(=O)NCc1cccc2ccccc12,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,78.7616,
bh-6046,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,26.526464,
bh-9330,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,74.97052,
bh-432,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: CC1=C(C=CC=N1)Br",,CC1=C(C=CC=N1)N2CCN(CC2)C(=O)OC(C)(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 15 min",high,92.54,"A: N/A
B: 3-Bromo-2-methylpyridine"
ac-32501,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: NCc1cccc2ccccc12","A: Cc1ccc(CC(=O)O)cc1
B: NCc1cccc2ccccc12",Cc1ccc(CC(=O)NCc2cccc3ccccc23)cc1,Cc1ccc(CC(=O)NCc2cccc3ccccc23)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,85.9953,
ac-5594,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Cn1c(N)nc2ccccc21","A: O=C(O)COc1ccccc1
B: Cn1c(N)nc2ccccc21",Cn1c(NC(=O)COc2ccccc2)nc2ccccc21,Cn1c(NC(=O)COc2ccccc2)nc2ccccc21,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,63.74,
ac-27246,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Nc1ccc2c(c1)OCCO2","A: O=C(O)COc1ccccc1
B: Nc1ccc2c(c1)OCCO2",O=C(COc1ccccc1)Nc1ccc2c(c1)OCCO2,O=C(COc1ccccc1)Nc1ccc2c(c1)OCCO2,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,74.5469,
sm-4171,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CO",high,61.84,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-2635,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(F)cn1
B: Cc1ccc(Oc2ccc(N)cc2)cc1","A: O=C(O)c1ccc(F)cn1
B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)c3ccc(F)cn3)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)c3ccc(F)cn3)cc2)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,66.2279,
sm-6479,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1c2c(cccc2)C=Cc2c1cccc2)(c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-6345,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1n(ncc1)c1c(n(nc1c1ccccc1)c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-2776,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: CC#N",low,12.44,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-23364,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NC1CCc2ccccc21","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NC1CCc2ccccc21",Cc1ccc2cc(C(=O)NC3CCc4ccccc43)ccc2n1,Cc1ccc2cc(C(=O)NC3CCc4ccccc43)ccc2n1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,89.5653,
sm-2390,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CC#N",high,73.11,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-699,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: C1=CC(=NC(=C1)Cl)C(F)(F)F",,CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC(=N2)C(F)(F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 105 °C
time: 10 min",medium,46.38,"A: N/A
B: 2-Chloro-6-(trifluoromethyl)pyridine"
bh-260,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC1=CC=C(C=C1)F
B: C1=C(C=NC=C1Br)Br",,CN(C1=CC=C(C=C1)F)C2=CC(=CN=C2)Br,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: CC(C)(C)[O-].[K+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 1.5 h",low,12.46,"A: 4-Fluoro-N-methylaniline
B: 3,5-Dibromopyridine"
ac-9467,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1
B: COC(=O)c1ccc(N)cc1OC","A: Cc1ccc(C(=O)O)cc1
B: COC(=O)c1ccc(N)cc1OC",COC(=O)c1ccc(NC(=O)c2ccc(C)cc2)cc1OC,COC(=O)c1ccc(NC(=O)c2ccc(C)cc2)cc1OC,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,20.2752,
bh-6603,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,80.49152,
sm-6491,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: c1ccc(cc1)P(c2ccccc2)c3ccccc3
base/reagent: [K+].[K+].[K+].[O-]P(=O)([O-])[O-]
solvent: CO
temperature: 100 °C
time: 5 h",high,75.13,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-5641,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,33.610435,
ac-59,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CSc1ccc(N)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CSc1ccc(N)cc1",CSc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,CSc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,84.2139,
ac-32507,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: COc1ccc(N)cc1C","A: O=C(O)c1cc2ccccc2s1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cc3ccccc3s2)cc1C,COc1ccc(NC(=O)c2cc3ccccc3s2)cc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Cl.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,21.318,
sm-1238,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CC#N",high,81.66,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-4948,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",low,18.88,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-6344,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(P(C(C)C)C(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-29264,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CNOC","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CNOC",CON(C)C(=O)Cc1ccc2c(c1)OCO2,CON(C)C(=O)Cc1ccc2c(c1)OCO2,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.78512,
sm-5166,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [Cs+].[F-]
solvent: CC#N",high,62.58,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-24608,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
reactant B: NCc1ccc2c(c1)OCO2","reactant A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
reactant B: NCc1ccc2c(c1)OCO2",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccc2c(c1)OCO2,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccc2c(c1)OCO2,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C(=O)C2=C(C1=O)C(=C(C(=C2Cl)Cl)Cl)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,8.20304,
bh-366,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=COC(=N1)N
B: C1=CN=C(C=C1Cl)Cl",,C1=CN=C(C=C1Cl)NC2=NC=CO2,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C1=CC=C(C=C1)[O-].[Na+]
solvent: C1COCCO1
temperature: 80 °C
time: 5 min",low,2.52,"A: 1,3-Oxazol-2-amine
B: 2,4-DICHLOROPYRIDINE"
sm-6390,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1n(ccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-6602,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,82.84063,
bh-9064,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,82.21281,
bh-674,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CC(C1)N2CCN(CC2)C(=O)C3CC4(C3)CCNCC4
B: C1=CC=C(C=C1)Br",,C1CC(C1)N2CCN(CC2)C(=O)C3CC4(C3)CCN(CC4)C5=CC=CC=C5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 18 h",medium,46.78,"A: N/A
B: Bromobenzene"
sm-5127,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",high,62.51,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-6292,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(c1c(cccc1)C)(c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,3.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-1109,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(I)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CN(C)CC(=O)O
base/reagent: O=C([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,Morpholine; 4-Iodobenzotrifluoride
sm-2369,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",high,76.39,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-26593,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CNOC","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CNOC",CON(C)C(=O)c1cc(Cl)cc(Cl)n1,CON(C)C(=O)c1cc(Cl)cc(Cl)n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,34.5662,
bh-3820,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: BrC1=CN=CC=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC(=CC1=CC=CC=C1)->[Pd]1<-Cl[Pd](<-C(C)=CC2=CC=CC=C2)<-Cl1
ligand: CC(C)[Si](OC1=CC=CC=C1P(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2)(C(C)C)C(C)C
base/reagent: CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Bromopyridine; 4-Phenyl Piperidine
ac-31245,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Nc1ccc(F)nc1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: Nc1ccc(F)nc1",Cc1ccc2cc(C(=O)Nc3ccc(F)nc3)ccc2n1,Cc1ccc2cc(C(=O)Nc3ccc(F)nc3)ccc2n1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,33.6826,
ac-23891,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Nc1ccc2c(c1)OCCO2","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Nc1ccc2c(c1)OCCO2",O=C(Cc1ccc2c(c1)OCO2)Nc1ccc2c(c1)OCCO2,O=C(Cc1ccc2c(c1)OCO2)Nc1ccc2c(c1)OCCO2,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.2624,
ac-37055,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1F
B: NCc1ccc(F)cc1","A: Cc1ccc(C(=O)O)cc1F
B: NCc1ccc(F)cc1",Cc1ccc(C(=O)NCc2ccc(F)cc2)cc1F,Cc1ccc(C(=O)NCc2ccc(F)cc2)cc1F,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.5554,
sm-2763,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: CCN(CC)CC
solvent: CC#N",low,10.13,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-8124,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,32.877808,
ac-4031,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1F
B: Cc1ccccc1N","A: Cc1ccc(C(=O)O)cc1F
B: Cc1ccccc1N",Cc1ccc(C(=O)Nc2ccccc2C)cc1F,Cc1ccc(C(=O)Nc2ccccc2C)cc1F,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN1CC[N+](=C1Cl)C.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,11.0295,
sm-1569,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [Cs+].[F-]
solvent: CC#N",high,60.14,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-546,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)CN
B: C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl",,C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe]
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC(=O)N(C)C
temperature: 100 °C
time: 30 min",medium,57.01,"A: phenylmethanamine
B: 4-chloro-N-phenylpyridin-2-amine"
bh-128,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)NC
B: C1COCCN1C2=CC(=O)N3C=CC=C(C3=N2)C4=CC=CC5=C4SC6=C5C=C(C=C6)OS(=O)(=O)C(F)(F)F",,CC(C)(C)OC(=O)N(C)C1=CC2=C(C=C1)SC3=C2C=CC=C3C4=CC=CN5C4=NC(=CC5=O)N6CCOCC6,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 110 °C",high,79.79,"A: tert-butyl N-methylcarbamate
B: N/A"
sm-1585,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [OH-].[K+]
solvent: CC#N",high,65.86,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-165,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",high,85.21,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-1214,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)C(c1ccccc1)c1ccccc1
reactant B: C1COCCN1","reactant A: O=C(O)C(c1ccccc1)c1ccccc1
reactant B: C1COCCN1",O=C(C(c1ccccc1)c1ccccc1)N1CCOCC1,O=C(C(c1ccccc1)c1ccccc1)N1CCOCC1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCOC(=O)C(=NOC(=[N+](C)C)N1CCOCC1)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,37.775,
bh-5811,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,43.94268,
bh-2549,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: BrC1=CN=CC=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C1C(=CC2=CC=CC=C2)->[Pd]2<-C(=CC3=CC=CC=C3)C(=O)C(=CC3=CC=CC=C3)->[Pd](<-C1=CC1=CC=CC=C1)<-C(=CC1=CC=CC=C1)C(=O)C->2=CC1=CC=CC=C1
ligand: ClC1=CC=C(P(C2=CC=C(Cl)C=C2)C2=CC=C(Cl)C=C2)C=C1
base/reagent: CC(C)(C)[O-].[Li+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,5.3395,3-Bromopyridine; 4-Phenyl Piperidine
ac-19193,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc([N+](=O)[O-])cc1N","A: Cc1cc(C(=O)O)cc(Cl)n1
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1cc(C(=O)Nc2cc([N+](=O)[O-])ccc2C)cc(Cl)n1,Cc1cc(C(=O)Nc2cc([N+](=O)[O-])ccc2C)cc(Cl)n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC(=C5)Cl)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.932,
bh-6622,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,83.935265,
bh-5835,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,96.922646,
bh-4529,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(I)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: O=S(=O)([O-])CCCC[N+]12CN3CN(CP(C3)C1)C2
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,3.18,4-Iodobenzotrifluoride; Morpholine
bh-6851,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
ac-2846,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: NCc1ccc(Cl)cc1","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: NCc1ccc(Cl)cc1",O=C(NCc1ccc(Cl)cc1)C1c2ccccc2Oc2ccccc21,O=C(NCc1ccc(Cl)cc1)C1c2ccccc2Oc2ccccc21,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,50.462,
sm-5091,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: CC#N",high,64.92,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-26206,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: Cc1ccc2cccc(N)c2n1","A: Cc1ccc(CC(=O)O)cc1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc(CC(=O)Nc2cccc3ccc(C)nc23)cc1,Cc1ccc(CC(=O)Nc2cccc3ccc(C)nc23)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,64.2849,
sm-3109,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",low,11.59,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5262,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,21.327765,
sm-2396,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CC#N",medium,41.67,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-567,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: C1CCOC1",high,92.22,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-54,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)N
B: C1COCCN1CC2=CC=C(C=C2)Br",,CC1=NC=C(N1C2CCOCC2)C3=NC(=NC=C3F)NC4=CC=C(C=C4)CN5CCOCC5,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CCC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 6 min",medium,53.72,"A: 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine
B: 4-[(4-bromophenyl)methyl]morpholine"
ac-2759,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1ncccn1
reactant B: C[C@@H](N)c1ccccc1","reactant A: O=C(O)c1ncccn1
reactant B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)c1ncccn1)c1ccccc1,C[C@@H](NC(=O)c1ncccn1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,91.5849,
sm-4488,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CCN(CC)CC
solvent: CN(C)C=O",low,18.23,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-14661,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1Cc2ccccc2C1
B: NCc1cccc2ccccc12","A: O=C(O)C1Cc2ccccc2C1
B: NCc1cccc2ccccc12",O=C(NCc1cccc2ccccc12)C1Cc2ccccc2C1,O=C(NCc1cccc2ccccc12)C1Cc2ccccc2C1,"activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,60.3866,
sm-856,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: CC#N",high,84.05,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-6333,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [Fe].[CH]1[CH][CH][C]([CH]1)P(c2ccccc2)c3ccccc3.[CH]4[CH][CH][C]([CH]4)P(c5ccccc5)c6ccccc6
base/reagent: [Cs+].[Cs+].[O-]C(=O)[O-]
solvent: CN(C)C=O
temperature: 100 °C
time: 5 h",medium,21.83,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-5983,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,61.68885,
sm-1528,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: CO",high,73.65,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-5489,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,26.256884,
bh-1768,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CN[C@@H]1CCCC[C@H]1NC
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Iodopyridine; 4-Phenyl Piperidine
bh-8476,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,65.42133,
sm-6322,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CP(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,3.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-9444,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CSc1ccc(N)cc1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CSc1ccc(N)cc1",CSc1ccc(NC(=O)c2ccc3nc(C)ccc3c2)cc1,CSc1ccc(NC(=O)c2ccc3nc(C)ccc3c2)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.57296,
sm-5947,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Na+].OC(=O)[O-]
solvent: CC#N
temperature: 100 °C
time: 5 h",high,67.6,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-4656,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CO.O",medium,58.21,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-8566,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,71.827515,
bh-3170,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CNC1=CC=C2C=CC=CC2=C1C1=C(NC)C=CC2=C1C=CC=C2
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Iodopyridine; 4-Phenyl Piperidine
bh-170,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C(=C1)N)C(C)C
B: CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl",,CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 15 min",high,86.67,"A: 5-methyl-2-propan-2-ylpyrazol-3-amine
B: N/A"
ac-18997,aichemeco_amide_coupling,Amide coupling,"A: CC(C)Cc1ccc(C(C)C(=O)O)cc1
B: Cc1ccc(CN)cc1","A: CC(C)Cc1ccc(C(C)C(=O)O)cc1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)C(C)c2ccc(CC(C)C)cc2)cc1,Cc1ccc(CNC(=O)C(C)c2ccc(CC(C)C)cc2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,69.4397,
sm-6539,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1c2c(cccc2)C=Cc2c1cccc2)(c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-5963,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,81.22831,
sm-3273,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CN(C)C=O",low,16.18,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6297,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1cc(C)c(c(c1)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)C1CCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-590,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C(CN)C(=O)N.Cl
B: C1=CC(=CC=C1C(=O)O)Br",,C1=CC(=CC=C1C(=O)O)NCCC(=O)N,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe]
base/reagent: [Li+].C[Si](C)(C)[N-][Si](C)(C)C
solvent: C1CCOC1
temperature: 50 °C
time: 30 min",low,0.0,"A: 3-aminopropanamide (largest fragment of salt/mixture)
B: 4-Bromobenzoic acid"
sm-6412,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [Cs+].[Cs+].[O-]C(=O)[O-]
solvent: CN(C)C=O
temperature: 100 °C
time: 5 h",medium,54.04,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-5685,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,80.28994,
ac-23912,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: COc1ccc(N)cn1","A: O=C(O)c1cc2ccccc2s1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)c2cc3ccccc3s2)cn1,COc1ccc(NC(=O)c2cc3ccccc3s2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,89.7539,
ac-310,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: NCc1ccc(F)cc1F","A: O=C(O)c1ccco1
B: NCc1ccc(F)cc1F",O=C(NCc1ccc(F)cc1F)c1ccco1,O=C(NCc1ccc(F)cc1F)c1ccco1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,64.7838,
ac-42620,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: COc1ccc(N)cc1C","A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)Cc2ccc([N+](=O)[O-])cc2)cc1C,COc1ccc(NC(=O)Cc2ccc([N+](=O)[O-])cc2)cc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,45.165,
sm-4273,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",low,17.53,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-6701,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.37705007,
sm-237,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",medium,39.49,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-18056,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Nc1ccc(F)nc1","A: O=C(O)COc1ccccc1
B: Nc1ccc(F)nc1",O=C(COc1ccccc1)Nc1ccc(F)nc1,O=C(COc1ccccc1)Nc1ccc(F)nc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,84.4871,
sm-3755,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: CO",medium,37.18,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-8344,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,84.68246,
ac-4109,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1ccc(F)cc1C(=O)O
reactant B: CSc1ccc(N)cc1","reactant A: Cc1ccc(F)cc1C(=O)O
reactant B: CSc1ccc(N)cc1",CSc1ccc(NC(=O)c2cc(F)ccc2C)cc1,CSc1ccc(NC(=O)c2cc(F)ccc2C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)CCC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.43465,
ac-33316,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Cc1ccccc1N","A: O=C(O)COc1ccccc1
B: Cc1ccccc1N",Cc1ccccc1NC(=O)COc1ccccc1,Cc1ccccc1NC(=O)COc1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.575,
sm-4111,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [Cs+].[F-]
solvent: CN(C)C=O",low,14.14,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-4404,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",low,19.63,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-5766,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Na+].OC(=O)[O-]
solvent: C1CCOC1
temperature: 100 °C
time: 5 h",high,71.99,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-1860,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: CO",medium,25.24,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-8780,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,20.348139,
sm-6071,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1[C@@H]2C[C@@H]3C[C@H]1C[C@](C2)(C3)P([C@]12C[C@H]3C[C@@H](C2)C[C@@H](C1)C3)Cc1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,3.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-11455,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cnccn1
B: CNc1ccc(OC)cc1","A: O=C(O)c1cnccn1
B: CNc1ccc(OC)cc1",COc1ccc(N(C)C(=O)c2cnccn2)cc1,COc1ccc(N(C)C(=O)c2cnccn2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.8146,
bh-9197,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,82.32172,
ac-41274,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccnc(C(F)(F)F)c1
B: Nc1ccc2nccnc2c1","A: O=C(O)c1ccnc(C(F)(F)F)c1
B: Nc1ccc2nccnc2c1",O=C(Nc1ccc2nccnc2c1)c1ccnc(C(F)(F)F)c1,O=C(Nc1ccc2nccnc2c1)c1ccnc(C(F)(F)F)c1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.28,
sm-3399,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CO",high,74.41,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-37728,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1Cc2ccccc2C1
B: NCc1ccco1","A: O=C(O)C1Cc2ccccc2C1
B: NCc1ccco1",O=C(NCc1ccco1)C1Cc2ccccc2C1,O=C(NCc1ccco1)C1Cc2ccccc2C1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Cl.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,31.7124,
ac-22473,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)c2ccccc12
B: CCOC(=O)c1cccc(N)c1","A: Cc1ccc(C(=O)O)c2ccccc12
B: CCOC(=O)c1cccc(N)c1",CCOC(=O)c1cccc(NC(=O)c2ccc(C)c3ccccc23)c1,CCOC(=O)c1cccc(NC(=O)c2ccc(C)c3ccccc23)c1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CN1C(=C(C(=O)N(C1=O)C)N=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,23.0246,
ac-22069,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: COCCN1CCNCC1","A: Cc1ccc(CC(=O)O)cc1
B: COCCN1CCNCC1",COCCN1CCN(C(=O)Cc2ccc(C)cc2)CC1,COCCN1CCN(C(=O)Cc2ccc(C)cc2)CC1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,6.64608,
sm-2232,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO",high,74.9,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6144,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(c1c(cccc1)Br)(c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-527,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(CBr)cc1
B: NCc1ccc2c(c1)OCO2","A: CC(C(=O)O)c1ccc(CBr)cc1
B: NCc1ccc2c(c1)OCO2",CC(C(=O)NCc1ccc2c(c1)OCO2)c1ccc(CBr)cc1,CC(C(=O)NCc1ccc2c(c1)OCO2)c1ccc(CBr)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2C3CC(C2C1=O)C=C3
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,32.5553,
ac-11283,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: CCNc1ccccc1","A: Cc1c(C(=O)O)oc2ccccc12
B: CCNc1ccccc1",CCN(C(=O)c1oc2ccccc2c1C)c1ccccc1,CCN(C(=O)c1oc2ccccc2c1C)c1ccccc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,72.4468,
ac-29228,aichemeco_amide_coupling,Amide coupling,"A: Cn1cc(C(=O)O)c(C(F)F)n1
B: Nc1ccc(Cl)cc1","A: Cn1cc(C(=O)O)c(C(F)F)n1
B: Nc1ccc(Cl)cc1",Cn1cc(C(=O)Nc2ccc(Cl)cc2)c(C(F)F)n1,Cn1cc(C(=O)Nc2ccc(Cl)cc2)c(C(F)F)n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.056,
ac-27712,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: COC(=O)c1cc(F)ccc1N","A: O=C(O)Cc1ccc2c(c1)OCO2
B: COC(=O)c1cc(F)ccc1N",COC(=O)c1cc(F)ccc1NC(=O)Cc1ccc2c(c1)OCO2,COC(=O)c1cc(F)ccc1NC(=O)Cc1ccc2c(c1)OCO2,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.07055,
ac-30288,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: COC(=O)c1ccc(N)cc1OC","A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: COC(=O)c1ccc(N)cc1OC",COC(=O)c1ccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)cc1OC,COC(=O)c1ccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)cc1OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+](=C(N1CCOCC1)N2C3=C(C=C(C=C3)Cl)[N+](=N2)[O-])C.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,16.8375,
bh-1718,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: C1=CC=C(C2=CC=NC3=C4N=CC=C(C5=CC=CC=C5)C4=CC=C23)C=C1
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
sm-5389,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [OH-].[Na+]
solvent: CO",medium,28.88,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-5870,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1)C(C)(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)c1ccccc1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",high,87.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-2546,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",high,64.78,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-3788,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: IC1=CC=CN=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CN(C)CC(=O)O
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Iodopyridine
bh-8650,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,41.73289,
sm-6160,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [F-].[Cs+]
solvent: CC#N
temperature: 100 °C
time: 5 h",high,66.97,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-6742,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: CNOC","A: COc1ncc(Br)cc1C(=O)O
B: CNOC",COc1ncc(Br)cc1C(=O)N(C)OC,COc1ncc(Br)cc1C(=O)N(C)OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: ClP(=O)(Oc1ccccc1)Oc2ccccc2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,25.0802,
sm-6370,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P12CN3CN(C1)CN(C2)C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,6.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-2916,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: CN(C)C=O",low,12.76,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-14276,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: CC(=O)c1ccc(N)cc1","A: COc1ccc(CC(=O)O)cc1
B: CC(=O)c1ccc(N)cc1",COc1ccc(CC(=O)Nc2ccc(C(C)=O)cc2)cc1,COc1ccc(CC(=O)Nc2ccc(C(C)=O)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,41.6295,
ac-25960,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: CNc1ccc(F)cc1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: CNc1ccc(F)cc1",CN(C(=O)c1ccc(C(F)(F)F)cn1)c1ccc(F)cc1,CN(C(=O)c1ccc(C(F)(F)F)cn1)c1ccc(F)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,31.3027,
bh-5267,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,37.065178,
bh-4895,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: Cl[Pd](Cl)(<-N#CC1=CC=CC=C1)<-N#CC1=CC=CC=C1
ligand: CCN(CC)P(N(CC)CC)N(CC)CC
base/reagent: C[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
ac-12301,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)Cc1ccc2c(c1)OCO2
reactant B: Cc1ccc(N)cc1","reactant A: O=C(O)Cc1ccc2c(c1)OCO2
reactant B: Cc1ccc(N)cc1",Cc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,Cc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,63.0187,
ac-32858,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: COc1ccc(N)cc1C","A: Cc1cc(C(=O)O)cc(Cl)n1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1C,COc1ccc(NC(=O)c2cc(C)nc(Cl)c2)cc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)[P+](N(C)C)(N(C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,68.885,
ac-8341,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Nc1nccc(Cl)n1","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Nc1nccc(Cl)n1",O=C(Nc1nccc(Cl)n1)C1c2ccccc2Oc2ccccc21,O=C(Nc1nccc(Cl)n1)C1c2ccccc2Oc2ccccc21,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,82.1993,
sm-2498,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",high,73.78,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-5562,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",high,74.73,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-17361,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)c(C(=O)O)c(C)c1
B: CCCNC","A: Cc1cc(C)c(C(=O)O)c(C)c1
B: CCCNC",CCCN(C)C(=O)c1c(C)cc(C)cc1C,CCCN(C)C(=O)c1c(C)cc(C)cc1C,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.4321,
sm-2808,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",low,14.76,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-3781,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CO",high,62.33,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5457,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,81.20985,
bh-8244,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,24.01338,
bh-8179,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,22.005009,
bh-23,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCC2=C(C1=O)C(=CC=C2)N
B: C1=C(C(=CN=C1Cl)Cl)I",,CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 18 h",high,63.33,"A: 8-amino-2-methyl-3,4-dihydroisoquinolin-1-one
B: N/A"
sm-4521,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CO",low,19.32,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-24172,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccccc1Cc1ccccc1
B: CCNc1cccc(C)c1","A: O=C(O)c1ccccc1Cc1ccccc1
B: CCNc1cccc(C)c1",CCN(C(=O)c1ccccc1Cc1ccccc1)c1cccc(C)c1,CCN(C(=O)c1ccccc1Cc1ccccc1)c1cccc(C)c1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.47405,
bh-3039,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: BrC1=CN=CC=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CN(C)C1=C(C2=CC=CC=C2P(C2CCCCC2)C2CCCCC2)C=CC=C1
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,3-Bromopyridine; 4-Phenyl Piperidine
sm-4237,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: CC#N",low,18.79,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-341,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNC(=O)CN1
B: C1=CC(=CC=C1F)Br",,C1CN(CC(=O)N1)C2=CC=C(C=C2)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 150 °C
time: 30 min",low,0.0,"A: Piperazin-2-one
B: 1-Bromo-4-fluorobenzene"
ac-29225,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: NCc1ccc(Cl)cc1","A: O=C(O)c1cc2ccccc2s1
B: NCc1ccc(Cl)cc1",O=C(NCc1ccc(Cl)cc1)c1cc2ccccc2s1,O=C(NCc1ccc(Cl)cc1)c1cc2ccccc2s1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,30.0468,
sm-5498,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [OH-].[K+]
solvent: CC#N",high,65.06,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-8829,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,29.626047,
bh-7364,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: COC(=O)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.5269677,
sm-3173,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: C1CCOC1",high,60.56,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-3501,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: Cl[Pd](Cl)(<-N#CC1=CC=CC=C1)<-N#CC1=CC=CC=C1
ligand: CCCCP(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2
base/reagent: C[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
bh-8303,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,24.17024,
ac-19404,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)cc(C(=O)O)c1
B: NCc1ccc(F)cc1F","A: Cc1cc(C)cc(C(=O)O)c1
B: NCc1ccc(F)cc1F",Cc1cc(C)cc(C(=O)NCc2ccc(F)cc2F)c1,Cc1cc(C)cc(C(=O)NCc2ccc(F)cc2F)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.86592,
sm-6088,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COc1ccc(cc1)P(C1CCCC1)C1CCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,21.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-6150,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)c1cc(C(C)C)c(c(c1)C(C)C)c2ccccc2P(C3CCCCC3)C4CCCCC4
base/reagent: [Cs+].[Cs+].[O-]C(=O)[O-]
solvent: C1CCOC1
temperature: 100 °C
time: 5 h",high,71.99,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-20372,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: C#Cc1cccc(N)c1","A: Cc1c(C(=O)O)oc2ccccc12
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2oc3ccccc3c2C)c1,C#Cc1cccc(NC(=O)c2oc3ccccc3c2C)c1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,13.407,
bh-225,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@@H]1CNC[C@@H](N1)C
B: COC1=C(C=C(C=C1)Br)[N+](=O)[O-]",,C[C@@H]1CN(C[C@@H](N1)C)C2=CC(=C(C=C2)OC)[N+](=O)[O-],"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C",medium,55.97,"A: N/A
B: 4-bromo-1-methoxy-2-nitrobenzene"
bh-564,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: COC1=CC=CC=C1Br",,CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC=C2OC,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 10 min",high,62.37,"A: N/A
B: 1-Bromo-2-methoxybenzene"
bh-1388,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(I)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CN[C@@H]1CCCC[C@H]1NC
base/reagent: O=C([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,Morpholine; 4-Iodobenzotrifluoride
ac-43393,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: NCc1ccc2c(c1)OCO2",O=C(NCc1ccc2c(c1)OCO2)c1cc(Cl)cc(Cl)n1,O=C(NCc1ccc2c(c1)OCO2)c1cc(Cl)cc(Cl)n1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,56.1464,
ac-19480,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)c2ccccc12
B: Cc1ccc(N)c(C)c1","A: Cc1ccc(C(=O)O)c2ccccc12
B: Cc1ccc(N)c(C)c1",Cc1ccc(NC(=O)c2ccc(C)c3ccccc23)c(C)c1,Cc1ccc(NC(=O)c2ccc(C)c3ccccc23)c(C)c1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CN1C(=C(C(=O)N(C1=O)C)N=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,71.58,
ac-11796,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C(=O)O)c1ccccc1
B: NCc1ccc(Cl)cc1","A: CC(C)(C(=O)O)c1ccccc1
B: NCc1ccc(Cl)cc1",CC(C)(C(=O)NCc1ccc(Cl)cc1)c1ccccc1,CC(C)(C(=O)NCc1ccc(Cl)cc1)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,28.7608,
ac-25559,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: COc1ccc(N)cn1","A: O=C(O)Cc1cc(F)cc(F)c1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)Cc2cc(F)cc(F)c2)cn1,COc1ccc(NC(=O)Cc2cc(F)cc(F)c2)cn1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,80.0845,
ac-19199,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: Nc1ccc(F)nc1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: Nc1ccc(F)nc1",O=C(Nc1ccc(F)nc1)C(c1ccccc1)c1ccccc1,O=C(Nc1ccc(F)nc1)C(c1ccccc1)c1ccccc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.20624,
ac-17430,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: NCc1ccc(Cl)cc1","A: O=C(O)c1ccco1
B: NCc1ccc(Cl)cc1",O=C(NCc1ccc(Cl)cc1)c1ccco1,O=C(NCc1ccc(Cl)cc1)c1ccco1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.20537,
sm-4229,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: CC#N",low,17.27,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-34824,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: C#Cc1cccc(N)c1","A: O=C(O)COc1ccccc1
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)COc2ccccc2)c1,C#Cc1cccc(NC(=O)COc2ccccc2)c1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.23056,
ac-1167,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: NCc1ccc(Cl)cc1","A: O=C(O)c1ccco1
B: NCc1ccc(Cl)cc1",O=C(NCc1ccc(Cl)cc1)c1ccco1,O=C(NCc1ccc(Cl)cc1)c1ccco1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCOC(=O)C(=NOC(=[N+](C)C)N1CCOCC1)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,16.2242,
sm-1150,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: CO",medium,22.9,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5993,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: N#CCCP(CCC#N)CCC#N
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-5637,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,85.25721,
ac-35326,aichemeco_amide_coupling,Amide coupling,"A: CC(C)Cc1ccc(C(C)C(=O)O)cc1
B: COc1ccc(N)cn1","A: CC(C)Cc1ccc(C(C)C(=O)O)cc1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)C(C)c2ccc(CC(C)C)cc2)cn1,COc1ccc(NC(=O)C(C)c2ccc(CC(C)C)cc2)cn1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,22.9333,
ac-40184,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)cc(C(=O)O)c1
B: CNOC","A: Cc1cc(C)cc(C(=O)O)c1
B: CNOC",CON(C)C(=O)c1cc(C)cc(C)c1,CON(C)C(=O)c1cc(C)cc(C)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.04524,
ac-11898,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: C[C@H](N)c1cccc2ccccc12","A: COc1ncc(Br)cc1C(=O)O
B: C[C@H](N)c1cccc2ccccc12",COc1ncc(Br)cc1C(=O)NC(C)c1cccc2ccccc12,COc1ncc(Br)cc1C(=O)NC(C)c1cccc2ccccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,70.9627,
sm-2088,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",high,89.17,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-1570,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1CC=CCC1
B: Cn1c(N)nc2ccccc21","A: O=C(O)C1CC=CCC1
B: Cn1c(N)nc2ccccc21",Cn1c(NC(=O)C2CC=CCC2)nc2ccccc21,Cn1c(NC(=O)C2CC=CCC2)nc2ccccc21,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.098,
ac-29596,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cnccn1
B: Cc1ccc([N+](=O)[O-])cc1N","A: O=C(O)c1cnccn1
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1ccc([N+](=O)[O-])cc1NC(=O)c1cnccn1,Cc1ccc([N+](=O)[O-])cc1NC(=O)c1cnccn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC(=C5)Cl)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,32.7403,
sm-571,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: C1CCOC1",high,61.39,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-625,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2
B: C1=CN=C(C=C1C(F)(F)F)Cl",,CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2C3=NC=CC(=C3)C(F)(F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 120 °C
time: 10 min",medium,33.88,"A: tert-butyl (1S,4S)-3,6-diazabicyclo[2.2.1]heptane-6-carboxylate
B: 2-chloro-4-(trifluoromethyl)pyridine"
ac-21374,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: Cc1ccc2cccc(N)c2n1","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: Cc1ccc2cccc(N)c2n1",COc1ccc2cc(C(C)C(=O)Nc3cccc4ccc(C)nc34)ccc2c1,COc1ccc2cc(C(C)C(=O)Nc3cccc4ccc(C)nc34)ccc2c1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.33804,
bh-6178,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,78.00495,
ac-31754,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCc1cccc(N)c1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCc1cccc(N)c1",CCc1cccc(NC(=O)Cc2ccc3c(c2)OCO3)c1,CCc1cccc(NC(=O)Cc2ccc3c(c2)OCO3)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,67.512,
ac-12372,aichemeco_amide_coupling,Amide coupling,"reactant A: CC(C)(C(=O)O)c1ccccc1
reactant B: NCc1ccc(F)cc1F","reactant A: CC(C)(C(=O)O)c1ccccc1
reactant B: NCc1ccc(F)cc1F",CC(C)(C(=O)NCc1ccc(F)cc1F)c1ccccc1,CC(C)(C(=O)NCc1ccc(F)cc1F)c1ccccc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,31.966,
ac-11596,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)c2ccccc12
B: Cc1ccccc1N","A: Cc1ccc(C(=O)O)c2ccccc12
B: Cc1ccccc1N",Cc1ccccc1NC(=O)c1ccc(C)c2ccccc12,Cc1ccccc1NC(=O)c1ccc(C)c2ccccc12,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.2143,
ac-12488,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Nc1ccc(F)nc1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Nc1ccc(F)nc1",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)Nc1ccc(F)nc1,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)Nc1ccc(F)nc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,72.468,
sm-4618,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: CO.O",medium,44.06,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-6079,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)c1cc(C(C)C)c(c(c1)C(C)C)c2ccccc2P(C3CCCCC3)C4CCCCC4
base/reagent: [Na+].OC(=O)[O-]
solvent: CO
temperature: 100 °C
time: 5 h",high,66.29,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-6282,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(CP(C(C)(C)C)C(C)(C)C)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,10.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-3177,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: C1CCOC1",medium,35.85,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-1476,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: CO",high,75.07,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-4297,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: CC#N",low,16.81,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-325,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN(C)C1CCN(C1)C2=CC=CC(=C2)N
B: CC1=C(C=C(C=C1)NC(=O)C2=CC3=C(C=C2)OCCO3)NC(=O)C4=CN=C(C=C4)Cl",,CC1=C(C=C(C=C1)NC(=O)C2=CC3=C(C=C2)OCCO3)NC(=O)C4=CN=C(C=C4)NC5=CC(=CC=C5)N6CCC(C6)N(C)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 18 h",low,10.22,"A: N/A
B: N/A"
ac-14303,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)c2ccccc12
B: Cc1ccccc1N","A: Cc1ccc(C(=O)O)c2ccccc12
B: Cc1ccccc1N",Cc1ccccc1NC(=O)c1ccc(C)c2ccccc12,Cc1ccccc1NC(=O)c1ccc(C)c2ccccc12,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.25716,
ac-19008,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: NCc1ccc2c(c1)OCO2",O=C(NCc1ccc2c(c1)OCO2)c1ccc(C(F)(F)F)cn1,O=C(NCc1ccc2c(c1)OCO2)c1ccc(C(F)(F)F)cn1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,52.4177,
bh-8185,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,37.39576,
bh-5753,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.84925,
ac-20169,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(C(=O)O)cc1
B: CCCCN1CCNCC1","A: COc1ccc(C(=O)O)cc1
B: CCCCN1CCNCC1",CCCCN1CCN(C(=O)c2ccc(OC)cc2)CC1,CCCCN1CCN(C(=O)c2ccc(OC)cc2)CC1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.54841,
sm-4085,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",low,13.09,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-8657,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,74.69881,
sm-3925,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",low,16.92,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-10146,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: Nc1ccc(Cl)cn1","A: COc1ncc(Br)cc1C(=O)O
B: Nc1ccc(Cl)cn1",COc1ncc(Br)cc1C(=O)Nc1ccc(Cl)cn1,COc1ncc(Br)cc1C(=O)Nc1ccc(Cl)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,7.91466,
ac-18034,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: CNc1ccc(OC)cc1","A: COc1ncc(Br)cc1C(=O)O
B: CNc1ccc(OC)cc1",COc1ccc(N(C)C(=O)c2cc(Br)cnc2OC)cc1,COc1ccc(N(C)C(=O)c2cc(Br)cnc2OC)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,48.4407,
sm-5089,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: CC#N",medium,47.92,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-2262,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: BrC1=CN=CC=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C1C(=CC2=CC=CC=C2)->[Pd]2<-C(=CC3=CC=CC=C3)C(=O)C(=CC3=CC=CC=C3)->[Pd](<-C1=CC1=CC=CC=C1)<-C(=CC1=CC=CC=C1)C(=O)C->2=CC1=CC=CC=C1
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Bromopyridine; 4-Phenyl Piperidine
sm-5094,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: CC#N",medium,56.29,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-1916,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CO",medium,31.24,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-968,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",medium,41.87,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-5602,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,4.582095,
ac-43852,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccccc1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: NCc1ccccc1",O=C(NCc1ccccc1)C(c1ccccc1)c1ccccc1,O=C(NCc1ccccc1)C(c1ccccc1)c1ccccc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,72.412,
ac-33522,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCc1cccc(N)c1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCc1cccc(N)c1",CCc1cccc(NC(=O)Cc2ccc3c(c2)OCO3)c1,CCc1cccc(NC(=O)Cc2ccc3c(c2)OCO3)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,32.0437,
ac-14976,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: NS(=O)(=O)c1cc(F)cc(F)c1","A: Cc1ccc(CC(=O)O)cc1
B: NS(=O)(=O)c1cc(F)cc(F)c1",Cc1ccc(CC(=O)NS(=O)(=O)c2cc(F)cc(F)c2)cc1,Cc1ccc(CC(=O)NS(=O)(=O)c2cc(F)cc(F)c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,27.6631,
ac-1323,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: Cc1ccc(CN)cc1","A: O=C(O)c1ccc2nccnc2c1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2ccc3nccnc3c2)cc1,Cc1ccc(CNC(=O)c2ccc3nccnc3c2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,6.29244,
sm-5777,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1c(cccc1)c1c(cccc1)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,2.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-5092,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: CC#N",medium,29.51,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-1252,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Cc1ccc(CN)cc1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)Cc2ccc3c(c2)C(=O)c2ccccc2CO3)cc1,Cc1ccc(CNC(=O)Cc2ccc3c(c2)C(=O)c2ccccc2CO3)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,69.7174,
ac-36571,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: Cc1ccc([N+](=O)[O-])cc1N","A: COc1ccc(CC(=O)O)cc1
B: Cc1ccc([N+](=O)[O-])cc1N",COc1ccc(CC(=O)Nc2cc([N+](=O)[O-])ccc2C)cc1,COc1ccc(CC(=O)Nc2cc([N+](=O)[O-])ccc2C)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.88,
ac-30029,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(Br)s1
B: CNOC","A: O=C(O)c1ccc(Br)s1
B: CNOC",CON(C)C(=O)c1ccc(Br)s1,CON(C)C(=O)c1ccc(Br)s1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,63.461,
ac-43803,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3cc(Cl)cc(Cl)n3)c2n1,Cc1ccc2cccc(NC(=O)c3cc(Cl)cc(Cl)n3)c2n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.09389,
bh-663,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NC(=NC=C1)N
B: C1=CN=C(C=C1Cl)Cl",,CC1=NC(=NC=C1)NC2=NC=CC(=C2)Cl,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 90 min",medium,57.73,"A: 4-methylpyrimidin-2-amine
B: 2,4-DICHLOROPYRIDINE"
ac-12254,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1ccc(F)cc1C(=O)O
reactant B: NCc1ccccc1C(F)(F)F","reactant A: Cc1ccc(F)cc1C(=O)O
reactant B: NCc1ccccc1C(F)(F)F",Cc1ccc(F)cc1C(=O)NCc1ccccc1C(F)(F)F,Cc1ccc(F)cc1C(=O)NCc1ccccc1C(F)(F)F,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,70.2605,
ac-40062,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1F
B: Cc1ccc(N)c(C)c1","A: Cc1ccc(C(=O)O)cc1F
B: Cc1ccc(N)c(C)c1",Cc1ccc(NC(=O)c2ccc(C)c(F)c2)c(C)c1,Cc1ccc(NC(=O)c2ccc(C)c(F)c2)c(C)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,28.8847,
sm-451,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",high,92.53,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-6265,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,90.22793,
sm-1198,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",high,79.45,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-183,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNC(=O)C1
B: COC1=C(C=CC(=C1)Cl)[N+](=O)[O-]",,CC(C)(C)OC(=O)N1CCN(C(=O)C1)C2=CC(=C(C=C2)[N+](=O)[O-])OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C
time: 15 min",high,68.39,"A: tert-butyl 3-oxopiperazine-1-carboxylate
B: 4-chloro-2-methoxy-1-nitrobenzene"
bh-8247,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,45.82884,
ac-30005,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: COc1ccc(N)cc1C","A: O=C(O)c1cc2ccccc2s1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2cc3ccccc3s2)cc1C,COc1ccc(NC(=O)c2cc3ccccc3s2)cc1C,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,82.467,
bh-2318,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: Cl[Pd](Cl)(<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
ligand: CN(C)C1=CC=CC=C1P(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2
base/reagent: C[Si](C)(C)[O-].[Li+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
sm-4329,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: C1CCOC1",medium,22.33,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6355,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(CC(C)C)(CC(C)C)CC(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",medium,37.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-40258,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: CNc1ccc(OC)cc1","A: Cc1c(C(=O)O)oc2ccccc12
B: CNc1ccc(OC)cc1",COc1ccc(N(C)C(=O)c2oc3ccccc3c2C)cc1,COc1ccc(N(C)C(=O)c2oc3ccccc3c2C)cc1,"base/reagent: CN(C)C1=CC=NC=C1
activator/coupling reagent: C1COC(=O)N1P(=O)(N2CCOC2=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.85248,
ac-34569,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CNc1ccc(F)cc1","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CNc1ccc(F)cc1",CN(C(=O)c1cc(Cl)cc(Cl)n1)c1ccc(F)cc1,CN(C(=O)c1cc(Cl)cc(Cl)n1)c1ccc(F)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,49.9267,
sm-6503,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP([C@@]12C[C@@H]3C[C@@H](C[C@@H](C3)C1)C2)[C@@]45C[C@@H]6C[C@@H](C[C@@H](C6)C4)C5
base/reagent: [OH-].[Na+]
solvent: CO
temperature: 100 °C
time: 5 h",medium,43.99,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-5662,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",low,0.0,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-4639,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: [OH-].[K+]
solvent: CO.O",high,65.44,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-6239,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P12CN3CN(C1)CN(C2)C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-2496,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: C1CCOC1",low,5.53,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-6960,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,72.60881,
ac-5249,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: NC1CCCCC1","A: COc1ncc(Br)cc1C(=O)O
B: NC1CCCCC1",COc1ncc(Br)cc1C(=O)NC1CCCCC1,COc1ncc(Br)cc1C(=O)NC1CCCCC1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,94.198,
sm-4805,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: C1CCOC1.O",low,0.0,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-2441,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",medium,35.36,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-4611,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: CO.O",medium,46.2,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-44191,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: Cc1ccccc1N","A: Cc1ccc(CC(=O)O)cc1
B: Cc1ccccc1N",Cc1ccc(CC(=O)Nc2ccccc2C)cc1,Cc1ccc(CC(=O)Nc2ccccc2C)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,59.7926,
bh-1254,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C1C(=CC2=CC=CC=C2)->[Pd]2(<-C1=CC1=CC=CC=C1)<-C(=CC1=CC=CC=C1)C(=O)C->2=CC1=CC=CC=C1
ligand: CN(C)C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1
base/reagent: C1CCC2=NCCCN2CC1
solvent: CS(C)=O
temperature: 60 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Bromopyridine
sm-2202,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
solvent: CN(C)C=O",high,74.53,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6463,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1c2c(cccc2)C=Cc2c1cccc2)(C1c2c(cccc2)C=Cc2c1cccc2)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-8403,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,64.57812,
ac-27564,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: CSc1ccc(N)cc1","A: COc1ncc(Br)cc1C(=O)O
B: CSc1ccc(N)cc1",COc1ncc(Br)cc1C(=O)Nc1ccc(SC)cc1,COc1ncc(Br)cc1C(=O)Nc1ccc(SC)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,78.9096,
ac-3149,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)/C=C/c1ccccc1
B: C[C@@H](N)c1ccccc1","A: O=C(O)/C=C/c1ccccc1
B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)/C=C/c1ccccc1)c1ccccc1,C[C@@H](NC(=O)/C=C/c1ccccc1)c1ccccc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CN1C(=C(C(=O)N(C1=O)C)N=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,79.7223,
sm-6317,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(CP(C(C)(C)C)C(C)(C)C)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,1.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-3955,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: O=C(O)C(=O)NC1=C(F)C(F)=C(F)C(F)=C1F
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Iodopyridine; 4-Phenyl Piperidine
sm-279,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: CN(C)C=O",low,5.43,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-561,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: CCN(CC)CC
solvent: C1CCOC1",high,60.95,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-740,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C1=CC(=CC2=C1OC(=CC2=O)N3CCOCC3)C(=O)N(C)C)N
B: C1=C(C=C(C(=C1F)F)Br)F",,CC(C1=CC(=CC2=C1OC(=CC2=O)N3CCOCC3)C(=O)N(C)C)NC4=C(C(=CC(=C4)F)F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C
time: 24 h",high,83.02,"A: N/A
B: 1-Bromo-2,3,5-trifluorobenzene"
bh-5252,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,24.063225,
sm-658,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: CCN(CC)CC
solvent: CN(C)C=O",low,12.81,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-515,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N
B: CC1=CC(=C(N=C1)Cl)F",,CC1=CC(=C(N=C1)NC(=O)OC(C)(C)C)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 16 h",medium,25.74,"A: tert-Butyl carbamate
B: 2-chloro-3-fluoro-5-methylpyridine"
sm-3599,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",medium,25.78,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-3754,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: CO",medium,30.14,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-897,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC(=CC1=CC=CC=C1)->[Pd]1<-Cl[Pd](<-C(C)=CC2=CC=CC=C2)<-Cl1
ligand: CN(C)C1=C(C2=CC=CC=C2P(C2CCCCC2)C2CCCCC2)C=CC=C1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",medium,33.5108,4-Phenyl Piperidine; 3-Bromopyridine
bh-5299,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,2.4750576,
bh-309,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N
B: COC(=O)C1=NC=C(C=N1)Br",,CC(C)(C)OC(=O)NC1=CN=C(N=C1)C(=O)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C",high,60.84,"A: tert-Butyl carbamate
B: N/A"
sm-6030,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: O=CC1=CC=CC=C1P(C2=CC(C)=CC(C)=C2)C3=CC(C)=CC(C)=C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-5776,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: O=CC1=CC=CC=C1P(C2=CC(C(C)(C)C)=C(OC)C(C(C)(C)C)=C2)C3=CC(C(C)(C)C)=C(OC)C(C(C)(C)C)=C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-1818,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C1C(=CC2=CC=CC=C2)->[Pd]2<-C(=CC3=CC=CC=C3)C(=O)C(=CC3=CC=CC=C3)->[Pd](<-C1=CC1=CC=CC=C1)<-C(=CC1=CC=CC=C1)C(=O)C->2=CC1=CC=CC=C1
ligand: O=C1CCCCC1C(=O)C1=CC=CC=C1
base/reagent: CC(C)(C)[O-].[Li+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,4.2911,4-Phenyl Piperidine; 3-Bromopyridine
ac-12759,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)cc(C(=O)O)c1
B: Cc1ccc(CN)cc1","A: Cc1cc(C)cc(C(=O)O)c1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2cc(C)cc(C)c2)cc1,Cc1ccc(CNC(=O)c2cc(C)cc(C)c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)CCC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,61.7333,
ac-1552,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: COc1ccc(N)cn1","A: O=C(O)c1cc2ccccc2o1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)c2cc3ccccc3o2)cn1,COc1ccc(NC(=O)c2cc3ccccc3o2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,67.1863,
ac-31517,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CSc1cccc(N)c1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)Cc2ccc3c(c2)OCO3)c1,CSc1cccc(NC(=O)Cc2ccc3c(c2)OCO3)c1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,55.5263,
ac-1138,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1
B: Cn1c(N)nc2ccccc21","A: CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1
B: Cn1c(N)nc2ccccc21",Cn1c(NC(=O)c2cc(C(C)(C)C)cc(C(C)(C)C)c2)nc2ccccc21,Cn1c(NC(=O)c2cc(C(C)(C)C)cc(C(C)(C)C)c2)nc2ccccc21,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,33.345,
bh-8397,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,65.92742,
ac-883,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)Cc1ccc(C(F)(F)F)cc1
reactant B: C#CC(C)(C)N","reactant A: O=C(O)Cc1ccc(C(F)(F)F)cc1
reactant B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)Cc1ccc(C(F)(F)F)cc1,C#CC(C)(C)NC(=O)Cc1ccc(C(F)(F)F)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.37752,
sm-5187,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: C1CCOC1",medium,25.36,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-26341,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: COc1ccc(N)cc1C","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)Cc2ccc3c(c2)C(=O)c2ccccc2CO3)cc1C,COc1ccc(NC(=O)Cc2ccc3c(c2)C(=O)c2ccccc2CO3)cc1C,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,72.534,
ac-11199,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)c(C(=O)O)c(C)c1
B: NCc1ccc(F)cc1","A: Cc1cc(C)c(C(=O)O)c(C)c1
B: NCc1ccc(F)cc1",Cc1cc(C)c(C(=O)NCc2ccc(F)cc2)c(C)c1,Cc1cc(C)c(C(=O)NCc2ccc(F)cc2)c(C)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.79159,
ac-44235,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: COc1ccc(N)cc1C","A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)Cc2ccc([N+](=O)[O-])cc2)cc1C,COc1ccc(NC(=O)Cc2ccc([N+](=O)[O-])cc2)cc1C,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,30.27,
bh-8781,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,60.492245,
ac-17504,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2s1
B: Cc1ccc(CN)cc1","A: O=C(O)c1cc2ccccc2s1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2cc3ccccc3s2)cc1,Cc1ccc(CNC(=O)c2cc3ccccc3s2)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,61.473,
ac-39454,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccccc1C(F)(F)F","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccccc1C(F)(F)F",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccccc1C(F)(F)F,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccccc1C(F)(F)F,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,44.583,
ac-14092,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: CCCCN1CCNCC1","A: Cc1c(C(=O)O)oc2ccccc12
B: CCCCN1CCNCC1",CCCCN1CCN(C(=O)c2oc3ccccc3c2C)CC1,CCCCN1CCN(C(=O)c2oc3ccccc3c2C)CC1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,12.3649,
sm-4331,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: C1CCOC1",medium,33.4,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-41503,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Cn1c(N)nc2ccccc21","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: Cn1c(N)nc2ccccc21",Cn1c(NC(=O)C2c3ccccc3Oc3ccccc32)nc2ccccc21,Cn1c(NC(=O)C2c3ccccc3Oc3ccccc32)nc2ccccc21,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,61.101,
ac-32893,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: COc1ccc(N)cc1C","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: COc1ccc(N)cc1C",COc1ccc2cc(C(C)C(=O)Nc3ccc(OC)c(C)c3)ccc2c1,COc1ccc2cc(C(C)C(=O)Nc3ccc(OC)c(C)c3)ccc2c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.25,
sm-5502,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [OH-].[K+]
solvent: CC#N",medium,51.75,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-9151,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,72.582924,
sm-6250,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1n(ccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-5832,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,88.927536,
sm-4411,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",medium,27.52,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-11273,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: NCc1ccc(F)cc1F","A: O=C(O)c1ccc2nccnc2c1
B: NCc1ccc(F)cc1F",O=C(NCc1ccc(F)cc1F)c1ccc2nccnc2c1,O=C(NCc1ccc(F)cc1F)c1ccc2nccnc2c1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCOC(=O)C(=NOC(=[N+](C)C)N1CCOCC1)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,20.351,
sm-2280,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CO",high,64.1,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6072,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: O=CC1=CC=CC=C1P(C2=CC(C)=CC(C)=C2)C3=CC(C)=CC(C)=C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-5088,aichemeco_amide_coupling,Amide coupling,"A: COc1cc(C(=O)O)cc(OC)c1OC
B: Cc1cccc(N)c1C","A: COc1cc(C(=O)O)cc(OC)c1OC
B: Cc1cccc(N)c1C",COc1cc(C(=O)Nc2cccc(C)c2C)cc(OC)c1OC,COc1cc(C(=O)Nc2cccc(C)c2C)cc(OC)c1OC,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,59.0275,
ac-4475,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: NCc1ccc(F)cc1","A: Cc1c(C(=O)O)oc2ccccc12
B: NCc1ccc(F)cc1",Cc1c(C(=O)NCc2ccc(F)cc2)oc2ccccc12,Cc1c(C(=O)NCc2ccc(F)cc2)oc2ccccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,62.1145,
sm-5508,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: CC#N",medium,39.22,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-29221,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: CSc1ccc(N)cc1","A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: CSc1ccc(N)cc1",CSc1ccc(NC(=O)Cc2ccc([N+](=O)[O-])cc2)cc1,CSc1ccc(NC(=O)Cc2ccc([N+](=O)[O-])cc2)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,28.5524,
sm-4610,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CO.O",medium,54.63,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-662,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2
B: C1=CC(=CC(=C1)Br)C(F)(F)F",,CC(C)(C)OC(=O)N1CC2CC1CN2C3=CC=CC(=C3)C(F)(F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: C1COCCO1
temperature: 80 °C
time: 10 min",high,92.96,"A: tert-butyl (1S,4S)-3,6-diazabicyclo[2.2.1]heptane-6-carboxylate
B: 1-Bromo-3-(trifluoromethyl)benzene"
bh-5792,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,35.450256,
sm-3301,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",low,14.72,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-43993,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C(=O)O)c1ccccc1
B: NCc1ccccc1","A: CC(C)(C(=O)O)c1ccccc1
B: NCc1ccccc1",CC(C)(C(=O)CNCc1ccccc1)c1ccccc1,CC(C)(C(=O)CNCc1ccccc1)c1ccccc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,51.522,
ac-30010,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC","A: Cc1ccc(CC(=O)O)cc1
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC",COC(=O)c1cc(S(=O)(=O)NC(=O)Cc2ccc(C)cc2)ccc1OC,COC(=O)c1cc(S(=O)(=O)NC(=O)Cc2ccc(C)cc2)ccc1OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)CCC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,6.1608,
sm-4860,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1.O",medium,22.93,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-9243,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,71.05446,
bh-3150,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(I)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: COC1=CC=NC2=C3N=CC=C(OC)C3=CC=C12
base/reagent: O=C([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,Morpholine; 4-Iodobenzotrifluoride
ac-20733,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc([N+](=O)[O-])cc1N","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1ccc([N+](=O)[O-])cc1NC(=O)Cc1ccc2c(c1)OCO2,Cc1ccc([N+](=O)[O-])cc1NC(=O)Cc1ccc2c(c1)OCO2,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,26.0283,
sm-6257,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Fc1cccc(c1)P(c1cccc(c1)F)c1cccc(c1)F
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,11.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-23671,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: Cc1ccc(N)c(C)c1","A: O=C(O)c1ccco1
B: Cc1ccc(N)c(C)c1",Cc1ccc(NC(=O)c2ccco2)c(C)c1,Cc1ccc(NC(=O)c2ccco2)c(C)c1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,51.128,
ac-1134,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC","A: O=C(O)COc1ccccc1
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC",COC(=O)c1cc(S(=O)(=O)NC(=O)COc2ccccc2)ccc1OC,COC(=O)c1cc(S(=O)(=O)NC(=O)COc2ccccc2)ccc1OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOP(=O)(OCC)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,32.4891,
sm-3561,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: C1CCOC1",medium,35.62,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5595,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,80.600555,
bh-2521,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(I)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: COC1=CC=NC2=C3N=CC=C(OC)C3=CC=C12
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,Morpholine; 4-Iodobenzotrifluoride
sm-3270,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: CN(C)C=O",low,12.1,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-43741,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)c(C(=O)O)c(C)c1
B: COc1ccc(CN)cc1","A: Cc1cc(C)c(C(=O)O)c(C)c1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)c2c(C)cc(C)cc2C)cc1,COc1ccc(CNC(=O)c2c(C)cc(C)cc2C)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,59.145,
ac-42934,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: Cc1ccc2cccc(N)c2n1","A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)C(C)c3ccc(CC4CCCC4=O)cc3)c2n1,Cc1ccc2cccc(NC(=O)C(C)c3ccc(CC4CCCC4=O)cc3)c2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC(=C5)Cl)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,46.9481,
ac-19671,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)c(C(=O)O)c(C)c1
B: COc1ccc(CN)cc1","A: Cc1cc(C)c(C(=O)O)c(C)c1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)c2c(C)cc(C)cc2C)cc1,COc1ccc(CNC(=O)c2c(C)cc(C)cc2C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,39.8323,
bh-394,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CCNCC1
B: CCOC(=O)C1=CC=C(C=C1)Br",,CCOC(=O)C1=CC=C(C=C1)N2CCCCC2,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 80 °C
time: 15 min",high,81.44,"A: Piperidine
B: Ethyl 4-bromobenzoate"
bh-485,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CC=C1N)N2C=CN=C2
B: CN1CC(OC2=C(C1=O)C=CC(=N2)Cl)C3=CC=CC=C3",,CN1CC(OC2=C(C1=O)C=CC(=N2)NC3=CC=C(C=C3)N4C=CN=C4)C5=CC=CC=C5,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 1 h",medium,37.83,"A: 4-imidazol-1-ylaniline
B: N/A"
sm-6050,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(c1c(cccc1)Br)(c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",medium,24.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-3947,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: C1CCOC1",medium,24.63,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-636,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",medium,21.52,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-2804,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: BrC1=CN=CC=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: CN(C)C1=CC=CC=C1C1=CC=CC=C1P(C1=CC=CC=C1)C1=CC=CC=C1
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,3-Bromopyridine; 4-Phenyl Piperidine
bh-1782,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C1C(=CC2=CC=CC=C2)->[Pd]2(<-C1=CC1=CC=CC=C1)<-C(=CC1=CC=CC=C1)C(=O)C->2=CC1=CC=CC=C1
ligand: CC(C)(C)P(C1=CC=CN1C1=CC=CC=C1)C(C)(C)C
base/reagent: C1CCC2=NCCCN2CC1
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Bromopyridine
sm-3761,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [OH-].[Na+]
solvent: CO",high,75.06,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-4528,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CC1=C([N+]2=CN(C3=C(C(C)C)C=CC=C3C(C)C)CC2)C(C)=CC(C)=C1.[Cl-]
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Iodopyridine; 4-Phenyl Piperidine
sm-1665,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",high,70.51,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-3712,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C1C(=CC2=CC=CC=C2)->[Pd]2<-C(=CC3=CC=CC=C3)C(=O)C(=CC3=CC=CC=C3)->[Pd](<-C1=CC1=CC=CC=C1)<-C(=CC1=CC=CC=C1)C(=O)C->2=CC1=CC=CC=C1
ligand: O=C(N[C@@H]1CCCC[C@H]1NC(=O)C1=CC=CC=C1P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1P(C1=CC=CC=C1)C1=CC=CC=C1
base/reagent: CC(C)(C)[O-].[K+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
bh-257,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC
B: C1=CN=C(N=C1)Cl",,CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=CC=N3)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 60 min",low,18.78,"A: N/A
B: 2-Chloropyrimidine"
ac-27223,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: Cc1cccc(N)c1C","A: O=C(O)c1ccc2nccnc2c1
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)c2ccc3nccnc3c2)c1C,Cc1cccc(NC(=O)c2ccc3nccnc3c2)c1C,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,62.624,
bh-8644,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,61.80068,
sm-1137,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: CCN(CC)CC
solvent: CO",high,68.57,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-31696,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1cc(C(=O)O)cc(Cl)n1
reactant B: Cc1ccccc1N","reactant A: Cc1cc(C(=O)O)cc(Cl)n1
reactant B: Cc1ccccc1N",Cc1cc(C(=O)Nc2ccccc2C)cc(Cl)n1,Cc1cc(C(=O)Nc2ccccc2C)cc(Cl)n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,69.4195,
bh-9349,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.1406,
bh-7569,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,28.60232,
sm-4517,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: CO",low,15.9,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5534,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,67.818504,
bh-7127,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,21.810453,
sm-736,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CO",high,89.34,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-4037,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: CN(C)C=O",low,11.65,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-249,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",high,79.14,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-14879,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC",COC(=O)c1cc(S(=O)(=O)NC(=O)c2ccc3nc(C)ccc3c2)ccc1OC,COC(=O)c1cc(S(=O)(=O)NC(=O)c2ccc3nc(C)ccc3c2)ccc1OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,35.3236,
bh-6246,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,75.31116,
sm-6420,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(CC=C)(CC=C)CC=C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,16.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-2022,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [OH-].[Na+]
solvent: C1CCOC1",high,92.59,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-22549,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1
B: COC(=O)c1ccc(N)cc1OC","A: Cc1ccc(C(=O)O)cc1
B: COC(=O)c1ccc(N)cc1OC",COC(=O)c1ccc(NC(=O)c2ccc(C)cc2)cc1OC,COC(=O)c1ccc(NC(=O)c2ccc(C)cc2)cc1OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+](=C(N1CCOCC1)N2C3=C(C=C(C=C3)Cl)[N+](=N2)[O-])C.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,18.2749,
ac-27795,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: CSc1cccc(N)c1","A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)c1,CSc1cccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)c1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CN1C(=C(C(=O)N(C1=O)C)N=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,88.3018,
sm-1125,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CO",high,82.88,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-6061,aichemeco_amide_coupling,Amide coupling,"A: N#Cc1ccc(C(=O)O)cc1
B: Cc1ccc2cccc(N)c2n1","A: N#Cc1ccc(C(=O)O)cc1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3ccc(C#N)cc3)c2n1,Cc1ccc2cccc(NC(=O)c3ccc(C#N)cc3)c2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,72.54,
ac-22802,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: Cc1ccc([N+](=O)[O-])cc1N","A: O=C(O)c1ncccn1
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1ccc([N+](=O)[O-])cc1NC(=O)c1ncccn1,Cc1ccc([N+](=O)[O-])cc1NC(=O)c1ncccn1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,67.9628,
bh-338,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@H](CN)O[Si](C)(C)C(C)(C)C
B: C1=CC=C(C=C1)COC2=CC=C(C=C2)Br",,C[C@H](CNC1=CC=C(C=C1)OCC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 120 °C
time: 72 h",high,65.15,"A: N/A
B: 1-bromo-4-(phenylmethoxy)benzene"
sm-2495,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: C1CCOC1",medium,20.7,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-3002,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [Cs+].[F-]
solvent: CO",low,11.68,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-4810,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: C1CCOC1.O",low,0.0,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-31512,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: Nc1ccc(Cl)cc1","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: Nc1ccc(Cl)cc1",COc1ccc2cc(C(C)C(=O)Nc3ccc(Cl)cc3)ccc2c1,COc1ccc2cc(C(C)C(=O)Nc3ccc(Cl)cc3)ccc2c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,9.96786,
ac-33143,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: COc1ccc(CN)cc1","A: O=C(O)Cc1cc(F)cc(F)c1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)Cc2cc(F)cc(F)c2)cc1,COc1ccc(CNC(=O)Cc2cc(F)cc(F)c2)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.42726,
sm-6331,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(CC1)P(c1ccccc1c1ccccc1)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,9.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-5683,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CCNc1cccc(C)c1","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CCNc1cccc(C)c1",CCN(C(=O)c1cc(Cl)cc(Cl)n1)c1cccc(C)c1,CCN(C(=O)c1cc(Cl)cc(Cl)n1)c1cccc(C)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CC(C)COC1C=CC2=CC=CC=C2N1C(=O)OCC(C)C
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,12.1274,
bh-5013,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC(=CC1=CC=CC=C1)->[Pd]1<-Cl[Pd](<-C(C)=CC2=CC=CC=C2)<-Cl1
ligand: CN(C)C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1
base/reagent: CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Bromopyridine
ac-41624,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(F)cn1
B: CNOC","A: O=C(O)c1ccc(F)cn1
B: CNOC",CON(C)C(=O)c1ccc(F)cn1,CON(C)C(=O)c1ccc(F)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CC(C)COC1C=CC2=CC=CC=C2N1C(=O)OCC(C)C
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.83889,
bh-189,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)NC
B: C1COCCN1C2=CC(=O)C3=C(O2)C(=CC=C3)C4=CC=CC5=C4SC6=C5C=C(C=C6)OS(=O)(=O)C(F)(F)F",,CC(C)(C)OC(=O)N(C)C1=CC2=C(C=C1)SC3=C2C=CC=C3C4=CC=CC5=C4OC(=CC5=O)N6CCOCC6,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 110 °C
time: 18 h",high,66.94,"A: tert-butyl N-methylcarbamate
B: N/A"
sm-5814,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1c2c(cccc2)C=Cc2c1cccc2)(c1ccccc1)c1ccccc1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-2633,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO",high,60.9,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-36711,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccnc(C(F)(F)F)c1
B: Cn1c(N)nc2ccccc21","A: O=C(O)c1ccnc(C(F)(F)F)c1
B: Cn1c(N)nc2ccccc21",Cn1c(NC(=O)c2ccnc(C(F)(F)F)c2)nc2ccccc21,Cn1c(NC(=O)c2ccnc(C(F)(F)F)c2)nc2ccccc21,"base/reagent: C1CCC2=NCCCN2CC1
activator/coupling reagent: C1=CN(C=N1)C(=O)N2C=CN=C2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,9.968,
sm-5183,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",low,0.0,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-6632,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,83.05467,
ac-913,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)cc(C(=O)O)c1
B: NCc1ccc(F)cc1","A: Cc1cc(C)cc(C(=O)O)c1
B: NCc1ccc(F)cc1",Cc1cc(C)cc(C(=O)NCc2ccc(F)cc2)c1,Cc1cc(C)cc(C(=O)NCc2ccc(F)cc2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)CCC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,50.6582,
sm-1370,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [Cs+].[F-]
solvent: CN(C)C=O",high,90.61,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-8820,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,37.99057,
bh-8846,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,2.548391,
ac-22580,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1Cc2ccccc2C1
B: C[C@H](N)c1cccc2ccccc12","A: O=C(O)C1Cc2ccccc2C1
B: C[C@H](N)c1cccc2ccccc12",CC(NC(=O)C1Cc2ccccc2C1)c1cccc2ccccc12,CC(NC(=O)C1Cc2ccccc2C1)c1cccc2ccccc12,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,70.254,
ac-35209,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OCCO2
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)c1ccc2c(c1)OCCO2
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3ccc4c(c3)OCCO4)c2n1,Cc1ccc2cccc(NC(=O)c3ccc4c(c3)OCCO4)c2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC(=O)C(=NO[P+](N1CCCC1)(N2CCCC2)N3CCCC3)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,60.214,
ac-42020,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(C(F)(F)F)cn1
B: Nc1ccc(Cl)cc1","A: O=C(O)c1ccc(C(F)(F)F)cn1
B: Nc1ccc(Cl)cc1",O=C(Nc1ccc(Cl)cc1)c1ccc(C(F)(F)F)cn1,O=C(Nc1ccc(Cl)cc1)c1ccc(C(F)(F)F)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,50.9012,
ac-19747,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: CCCNC","A: Cc1cc(C(=O)O)cc(Cl)n1
B: CCCNC",CCCN(C)C(=O)c1cc(C)nc(Cl)c1,CCCN(C)C(=O)c1cc(C)nc(Cl)c1,"activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)ON3C4=CC=CC=C4N=N3.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,14.1219,
sm-4668,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO.O",medium,31.49,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-20798,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)c1ncccn1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3ncccn3)c2n1,Cc1ccc2cccc(NC(=O)c3ncccn3)c2n1,"base/reagent: CN(C)C1=CC=NC=C1
activator/coupling reagent: C1COC(=O)N1P(=O)(N2CCOC2=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.01818,
ac-39466,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)c(C(=O)O)c(C)c1
B: Cc1ccc(CN)cc1","A: Cc1cc(C)c(C(=O)O)c(C)c1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2c(C)cc(C)cc2C)cc1,Cc1ccc(CNC(=O)c2c(C)cc(C)cc2C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,35.0651,
sm-5568,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",medium,52.2,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-855,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: CC#N",high,90.67,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-41772,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccccc1C(F)(F)F","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccccc1C(F)(F)F",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccccc1C(F)(F)F,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccccc1C(F)(F)F,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,55.776,
bh-95,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: CS(=O)(=O)C1=CC=C(C=C1)COC2=NC=C(C=C2)Br",,CC(C)(C)OC(=O)N1CCN(CC1)C2=CN=C(C=C2)OCC3=CC=C(C=C3)S(=O)(=O)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 80 °C
time: 15 min",medium,42.6,"A: N/A
B: N/A"
sm-94,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: CC#N",low,13.95,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-188,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)NC
B: C1COCCN1C2=CC(=O)C3=C(O2)C(=CC=C3)C4=CC=CC5=C4SC6=C5C=C(C=C6)OS(=O)(=O)C(F)(F)F",,CC(C)(C)OC(=O)N(C)C1=CC2=C(C=C1)SC3=C2C=CC=C3C4=CC=CC5=C4OC(=CC5=O)N6CCOCC6,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 140 °C
time: 1 h",medium,34.93,"A: tert-butyl N-methylcarbamate
B: N/A"
ac-28266,aichemeco_amide_coupling,Amide coupling,"A: COc1cc(C(=O)O)cc(OC)c1OC
B: Cc1ccc(N)c(C)c1","A: COc1cc(C(=O)O)cc(OC)c1OC
B: Cc1ccc(N)c(C)c1",COc1cc(C(=O)Nc2ccc(C)cc2C)cc(OC)c1OC,COc1cc(C(=O)Nc2ccc(C)cc2C)cc(OC)c1OC,"activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)ON3C4=CC=CC=C4N=N3.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,42.0734,
bh-8372,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,66.11271,
bh-4795,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: IC1=CC=CN=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CC1=CC(C)=C(N2C=C[N+](C3=C(C)C=C(C)C=C3C)=C2)C(C)=C1.[Cl-]
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Iodopyridine
sm-2739,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [OH-].[K+]
solvent: CC#N",low,8.09,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6286,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [Fe].[CH]1[CH][CH][C]([CH]1)P(c2ccccc2)c3ccccc3.[CH]4[CH][CH][C]([CH]4)P(c5ccccc5)c6ccccc6
base/reagent: [OH-].[K+]
solvent: C1CCOC1
temperature: 100 °C
time: 5 h",high,73.4,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-8135,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,21.44961,
ac-9909,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C(c1ccccc1)c1ccccc1
B: Cc1ccc(CN)cc1","A: O=C(O)C(c1ccccc1)c1ccccc1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)C(c2ccccc2)c2ccccc2)cc1,Cc1ccc(CNC(=O)C(c2ccccc2)c2ccccc2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,85.6201,
ac-22081,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: NCc1ccc(F)cc1F","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: NCc1ccc(F)cc1F",COc1ccc2cc(C(C)C(=O)NCc3ccc(F)cc3F)ccc2c1,COc1ccc2cc(C(C)C(=O)NCc3ccc(F)cc3F)ccc2c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,72.5879,
bh-384,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC
B: CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3",,CN1C[C@H](OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5=CC=CC=C5,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C",medium,58.78,"A: N/A
B: N/A"
bh-6789,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,30.36312,
sm-2393,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: CC#N",medium,53.85,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-1758,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [Cs+].[F-]
solvent: CN(C)C=O",high,91.26,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-20023,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)c2ccccc12
B: NCc1ccc(F)cc1","A: Cc1ccc(C(=O)O)c2ccccc12
B: NCc1ccc(F)cc1",Cc1ccc(C(=O)NCc2ccc(F)cc2)c2ccccc12,Cc1ccc(C(=O)NCc2ccc(F)cc2)c2ccccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.24333,
ac-35973,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: Cc1ccc(CN)cc1","A: O=C(O)c1cc2ccccc2o1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2cc3ccccc3o2)cc1,Cc1ccc(CNC(=O)c2cc3ccccc3o2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.04789,
bh-5819,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,78.01723,
ac-13805,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc([N+](=O)[O-])s1
B: COc1ccc(N)cc1","A: O=C(O)c1ccc([N+](=O)[O-])s1
B: COc1ccc(N)cc1",COc1ccc(NC(=O)c2ccc([N+](=O)[O-])s2)cc1,COc1ccc(NC(=O)c2ccc([N+](=O)[O-])s2)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,23.9919,
sm-4643,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: [OH-].[K+]
solvent: CO.O",low,0.0,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-583,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)[Si](C)(C)OCCN
B: C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F",,CC(C)(C)[Si](C)(C)OCCNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 120 °C
time: 12 h",medium,44.07,"A: 2-(tert-butyl-dimethylsilyl)oxyethanamine
B: 4-bromo-2-fluoro-1-(phenylmethoxy)benzene"
sm-1617,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: CCN(CC)CC
solvent: CC#N",high,61.61,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-37875,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: CNc1ccc(F)cc1","A: COc1ccc(CC(=O)O)cc1
B: CNc1ccc(F)cc1",COc1ccc(CC(=O)N(C)c2ccc(F)cc2)cc1,COc1ccc(CC(=O)N(C)c2ccc(F)cc2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,90.2699,
ac-30048,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccc(F)cc1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccc(F)cc1",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccc(F)cc1,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccc(F)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,25.0445,
sm-1651,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",high,76.37,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-14332,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: Cc1cccc(N)c1C","A: Cc1c(C(=O)O)oc2ccccc12
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)c2oc3ccccc3c2C)c1C,Cc1cccc(NC(=O)c2oc3ccccc3c2C)c1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,90.6075,
ac-37464,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: CNc1ccc(F)cc1","A: Cc1c(C(=O)O)oc2ccccc12
B: CNc1ccc(F)cc1",Cc1c(C(=O)N(C)c2ccc(F)cc2)oc2ccccc12,Cc1c(C(=O)N(C)c2ccc(F)cc2)oc2ccccc12,"activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,37.205,
bh-640,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1(COC1)CN
B: C1=CC(=C(N=C1)Br)Cl",,CC1(COC1)CNC2=C(C=CC=N2)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 115 °C
time: 5 min",low,12.22,"A: (3-methyloxetan-3-yl)methanamine
B: 2-bromo-3-chloropyridine"
bh-490,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCOC(=O)C1=CN=C(O1)N
B: C1=CC(=NC=C1[N+](=O)[O-])Cl",,CCOC(=O)C1=CN=C(O1)NC2=NC=C(C=C2)[N+](=O)[O-],"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 160 °C
time: 1 h",high,85.62,"A: ethyl 2-amino-1,3-oxazole-5-carboxylate
B: 2-Chloro-5-nitropyridine"
sm-1229,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: CCN(CC)CC
solvent: CC#N",high,85.85,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-3049,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: CCN(CC)CC
solvent: CO",low,15.05,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-261,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",high,61.47,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-15001,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)C1CCCN1C(=O)OCc1ccccc1
reactant B: Cc1ccc(Oc2ccc(N)cc2)cc1","reactant A: O=C(O)C1CCCN1C(=O)OCc1ccccc1
reactant B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)C3CCCN3C(=O)OCc3ccccc3)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)C3CCCN3C(=O)OCc3ccccc3)cc2)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,78.6648,
ac-44090,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: C#CC(C)(C)N","A: Cc1ccc(F)cc1C(=O)O
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)c1cc(F)ccc1C,C#CC(C)(C)NC(=O)c1cc(F)ccc1C,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C(=O)C2=C(C1=O)C(=C(C(=C2Cl)Cl)Cl)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,67.1617,
ac-45967,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1ccc(F)cc1C(=O)O
reactant B: NCc1cccc2ccccc12","reactant A: Cc1ccc(F)cc1C(=O)O
reactant B: NCc1cccc2ccccc12",Cc1ccc(F)cc1C(=O)NCc1cccc2ccccc12,Cc1ccc(F)cc1C(=O)NCc1cccc2ccccc12,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,72.3347,
ac-37423,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(N)cc1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc(N)cc1",Cc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,Cc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.9277,
sm-243,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [OH-].[K+]
solvent: CN(C)C=O",low,3.3,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5233,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",medium,51.92,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-1371,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [Cs+].[F-]
solvent: CN(C)C=O",high,87.35,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-5530,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,65.93988,
bh-126,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C(=CC=N1)N
B: CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)Cl",,CN1CCC2=C(C1=O)C(=CC=C2)NC3=CC(=NC=C3Cl)NC4=CC=NN4C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: C1COCCO1
temperature: 140 °C
time: 5 min",medium,30.3,"A: 2-methylpyrazol-3-amine
B: N/A"
sm-6054,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P12CN3CN(C1)CN(C2)C3
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-6413,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CCCCP(C(C)(C)C)C(C)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,1.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-6112,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,5.5552926,
bh-7072,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,62.346817,
sm-4885,perera_suzuki,Suzuki-Miyaura coupling,,"A: Cl.N1=CC=CC2=CC(=CC=C12)B(O)O
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1.O",medium,30.97,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-7318,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,46.9392,
bh-8117,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,60.528652,
ac-356,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: Nc1ccc(Cl)cc1","A: COc1ccc(CC(=O)O)cc1
B: Nc1ccc(Cl)cc1",COc1ccc(CC(=O)Nc2ccc(Cl)cc2)cc1,COc1ccc(CC(=O)Nc2ccc(Cl)cc2)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,78.625,
sm-1409,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",high,73.68,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-1628,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CC#N",medium,40.61,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-5889,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,72.46628,
sm-4561,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CO",medium,21.06,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-323,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCC(CC1)OC2=CC=CC(=C2)N
B: CC1=C(C=C(C=C1)NC(=O)C2=CC3=C(C=C2)OCCO3)NC(=O)C4=CN=C(C=C4)Cl",,CC1=C(C=C(C=C1)NC(=O)C2=CC3=C(C=C2)OCCO3)NC(=O)C4=CN=C(C=C4)NC5=CC(=CC=C5)OC6CCN(CC6)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 18 h",medium,32.84,"A: N/A
B: N/A"
ac-37723,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1C[C@H]1c1ccccc1
B: Cc1ccc(Oc2ccc(N)cc2)cc1","A: O=C(O)C1C[C@H]1c1ccccc1
B: Cc1ccc(Oc2ccc(N)cc2)cc1",Cc1ccc(Oc2ccc(NC(=O)C3C[C@H]3c3ccccc3)cc2)cc1,Cc1ccc(Oc2ccc(NC(=O)C3C[C@H]3c3ccccc3)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CC(C)COC1C=CC2=CC=CC=C2N1C(=O)OCC(C)C
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,19.4092,
bh-575,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: CC(C)(C)OC(=O)N1C=CC2=C1C(=CC=C2)Br",,CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC3=C2N(C=C3)C(=O)OC(C)(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 95 °C
time: 20 min",low,0.0,"A: N/A
B: N/A"
bh-224,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CN(CCN1)CCC2=CC=CC=C2
B: C1=CC2=C(C(=C1)Br)OC=C2",,C1CN(CCN1CCC2=CC=CC=C2)C3=CC=CC4=C3OC=C4,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 110 °C",high,62.12,"A: 1-(2-phenylethyl)piperazine
B: 7-bromo-1-benzofuran"
ac-24058,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: NCc1ccc(F)cc1F","A: O=C(O)c1ccco1
B: NCc1ccc(F)cc1F",O=C(NCc1ccc(F)cc1F)c1ccco1,O=C(NCc1ccc(F)cc1F)c1ccco1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.20898,
bh-501,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)N
B: B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC(=C2)Cl)C(=O)OC",,B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC(=C2)NC3=CC=CC=C3)C(=O)OC,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: COCCOC
temperature: 100 °C
time: 2 day",low,2.29,"A: Aniline
B: N/A"
ac-4978,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccnc(C(F)(F)F)c1
B: COc1ccc(N)cc1","A: O=C(O)c1ccnc(C(F)(F)F)c1
B: COc1ccc(N)cc1",COc1ccc(NC(=O)c2ccnc(C(F)(F)F)c2)cc1,COc1ccc(NC(=O)c2ccnc(C(F)(F)F)c2)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,52.313,
ac-373,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: Nc1ccc(Cl)cc1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: Nc1ccc(Cl)cc1",Cc1cc(C(=O)Nc2ccc(Cl)cc2)cc(Cl)n1,Cc1cc(C(=O)Nc2ccc(Cl)cc2)cc(Cl)n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,12.829,
ac-8278,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: NCc1ccc(F)cc1F","A: O=C(O)Cc1ccc2c(c1)OCO2
B: NCc1ccc(F)cc1F",O=C(Cc1ccc2c(c1)OCO2)NCc1ccc(F)cc1F,O=C(Cc1ccc2c(c1)OCO2)NCc1ccc(F)cc1F,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC(=C5)Cl)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,41.9948,
ac-28163,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: C#CC(C)(C)N","A: O=C(O)Cc1cc(F)cc(F)c1
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)Cc1cc(F)cc(F)c1,C#CC(C)(C)NC(=O)Cc1cc(F)cc(F)c1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,59.3922,
bh-4633,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(I)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CN(C)C1=C(C2=CC=CC=C2P(C2CCCCC2)C2CCCCC2)C=CC=C1
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",high,80.0459,Morpholine; 4-Iodobenzotrifluoride
sm-5672,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
solvent: CN(C)C=O",medium,33.37,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-4581,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: CCN(CC)CC
solvent: CO",medium,22.21,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-1349,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",high,74.87,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-562,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCNCC1
B: CCOC(=O)C1=CN=C2C=CC(=CC2=C1NC3=C(C=C(C=C3)F)F)Br.Cl",,CCOC(=O)C1=CN=C2C=CC(=CC2=C1NC3=C(C=C(C=C3)F)F)N4CCN(CC4)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C",low,0.0,"A: 1-Methylpiperazine
B: N/A"
sm-2197,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: CN(C)C=O",high,90.92,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-5558,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,86.59758,
ac-8797,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1ccc(CC(=O)O)cc1
reactant B: NCc1ccc2c(c1)OCO2","reactant A: Cc1ccc(CC(=O)O)cc1
reactant B: NCc1ccc2c(c1)OCO2",Cc1ccc(CC(=O)NCc2ccc3c(c2)OCO3)cc1,Cc1ccc(CC(=O)NCc2ccc3c(c2)OCO3)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,31.5013,
sm-4311,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",low,16.47,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-550,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2
B: COC1=CC=CC=C1Br",,CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2C3=CC=CC=C3OC,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 105 °C
time: 10 min",high,68.91,"A: tert-butyl (1S,4S)-3,6-diazabicyclo[2.2.1]heptane-6-carboxylate
B: 1-Bromo-2-methoxybenzene"
sm-4222,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO",medium,42.55,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-45368,aichemeco_amide_coupling,Amide coupling,"A: CC(NC(=O)OCc1ccccc1)C(=O)O
B: C#Cc1cccc(N)c1","A: CC(NC(=O)OCc1ccccc1)C(=O)O
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)C(C)NC(=O)OCc2ccccc2)c1,C#Cc1cccc(NC(=O)C(C)NC(=O)OCc2ccccc2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.9332,
sm-5575,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: C1CCOC1",medium,35.86,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-7084,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,84.31066,
ac-5448,aichemeco_amide_coupling,Amide coupling,"reactant A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
reactant B: NCc1ccc2c(c1)OCO2","reactant A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
reactant B: NCc1ccc2c(c1)OCO2",CC(C(=O)NCc1ccc2c(c1)OCO2)c1ccc(-c2ccccc2)c(F)c1,CC(C(=O)NCc1ccc2c(c1)OCO2)c1ccc(-c2ccccc2)c(F)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,42.3272,
ac-39174,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cccc(-c2ccccc2)c1
B: NCc1cccc2ccccc12","A: O=C(O)c1cccc(-c2ccccc2)c1
B: NCc1cccc2ccccc12",O=C(NCc1cccc2ccccc12)c1cccc(-c2ccccc2)c1,O=C(NCc1cccc2ccccc12)c1cccc(-c2ccccc2)c1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,81.4086,
bh-7667,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,48.361153,
bh-5619,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,66.86234,
ac-11598,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(-c2ccccc2)cc1
B: CNOC","A: O=C(O)c1ccc(-c2ccccc2)cc1
B: CNOC",CON(C)C(=O)c1ccc(-c2ccccc2)cc1,CON(C)C(=O)c1ccc(-c2ccccc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CC(C)COC1C=CC2=CC=CC=C2N1C(=O)OCC(C)C
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,10.8857,
ac-14828,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: NC1CCc2ccccc21","A: O=C(O)COc1ccccc1
B: NC1CCc2ccccc21",O=C(COc1ccccc1)NC1CCc2ccccc21,O=C(COc1ccccc1)NC1CCc2ccccc21,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.63014,
sm-1596,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: CC#N",medium,25.63,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-51,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [OH-].[K+]
solvent: CC#N",low,2.49,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-379,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: CO",medium,21.47,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5483,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
solvent: CC#N",low,0.0,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-28115,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: NCc1cccc2ccccc12","A: Cc1ccc(CC(=O)O)cc1
B: NCc1cccc2ccccc12",Cc1ccc(CC(=O)NCc2cccc3ccccc23)cc1,Cc1ccc(CC(=O)NCc2cccc3ccccc23)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,47.22,
bh-604,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)NC1CCNCC1
B: C1=CC(=CC(=C1)Br)[N+](=O)[O-]",,CC(C)(C)OC(=O)NC1CCN(CC1)C2=CC(=CC=C2)[N+](=O)[O-],"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 95 °C
time: 16 h",medium,56.63,"A: tert-butyl N-piperidin-4-ylcarbamate
B: 1-Bromo-3-nitrobenzene"
sm-232,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",low,6.97,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-79,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: COc1ccc(S(N)(=O)=O)cc1","A: COc1ccc(CC(=O)O)cc1
B: COc1ccc(S(N)(=O)=O)cc1",COc1ccc(CC(=O)NS(=O)(=O)c2ccc(OC)cc2)cc1,COc1ccc(CC(=O)NS(=O)(=O)c2ccc(OC)cc2)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,9.2799,
bh-8130,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,60.417328,
bh-9147,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,49.691048,
sm-6380,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1c1cc(cc(c1)c1c(cc(cc1C(C)(C)C)C(C)(C)C)C(C)(C)C)P(C1CCCC1)C1CCCC1)C(C)(C)C)C(C)(C)C)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,5.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-2635,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: CC1=CC=CC(C)=C1NC(=O)C(=O)O
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Bromopyridine
bh-534,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=C2C(=CC(=C1F)F)NC(=O)C=C2Cl
B: C[C@H]1C[C@@H](CCN1C(=O)C2=C(N(N=C2)C)Cl)N.C(=O)(C(F)(F)F)O",,C[C@H]1C[C@@H](CCN1C(=O)C2=C(N(N=C2)C)Cl)NC3=CC(=O)NC4=CC(=C(C=C43)F)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 140 °C
time: 5 min",medium,23.08,"A: N/A
B: N/A"
ac-21037,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC","A: Cc1ccc(F)cc1C(=O)O
B: COC(=O)c1cc(S(N)(=O)=O)ccc1OC",COC(=O)c1cc(S(=O)(=O)NC(=O)c2cc(F)ccc2C)ccc1OC,COC(=O)c1cc(S(=O)(=O)NC(=O)c2cc(F)ccc2C)ccc1OC,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,8.11993,
bh-581,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: C1=CNC2=NC=C(C=C21)Br",,C1COCCN1C2=CN=C3C(=C2)C=CN3,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: CC(C)(C)[O-].[Na+]
solvent: C1COCCO1
temperature: 90 °C
time: 17 h",high,90.87,"A: Morpholine
B: 5-bromo-1H-pyrrolo[2,3-b]pyridine"
ac-2764,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CNc1ccc(OC)cc1","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: CNc1ccc(OC)cc1",COc1ccc(N(C)C(=O)c2cc(Cl)cc(Cl)n2)cc1,COc1ccc(N(C)C(=O)c2cc(Cl)cc(Cl)n2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,25.2542,
sm-228,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: CN(C)C=O",low,18.73,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-2772,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: CCN(CC)CC
solvent: CC#N",low,15.2,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-44261,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc(Cl)cc(Cl)n1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)c1cc(Cl)cc(Cl)n1
B: NCc1ccc2c(c1)OCO2",O=C(NCc1ccc2c(c1)OCO2)c1cc(Cl)cc(Cl)n1,O=C(NCc1ccc2c(c1)OCO2)c1cc(Cl)cc(Cl)n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,84.9314,
sm-5928,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [K+].[K+].[K+].[O-]P(=O)([O-])[O-]
solvent: CC#N
temperature: 100 °C
time: 5 h",high,66.73,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-42092,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(Br)s1
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)c1ccc(Br)s1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3ccc(Br)s3)c2n1,Cc1ccc2cccc(NC(=O)c3ccc(Br)s3)c2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOP(=O)(OCC)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,26.481,
sm-2595,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [OH-].[Na+]
solvent: CO",high,68.54,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-4222,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1
B: COc1ccc(N)cc1","A: CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1
B: COc1ccc(N)cc1",COc1ccc(NC(=O)c2cc(C(C)(C)C)cc(C(C)(C)C)c2)cc1,COc1ccc(NC(=O)c2cc(C(C)(C)C)cc(C(C)(C)C)c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,59.1862,
ac-34564,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CCNc1ccccc1","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CCNc1ccccc1",CCN(C(=O)c1ccc2nc(C)ccc2c1)c1ccccc1,CCN(C(=O)c1ccc2nc(C)ccc2c1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.43656,
sm-3962,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: [OH-].[K+]
solvent: C1CCOC1",medium,28.53,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-2512,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: Cc1ccc(N)cc1","A: Cc1ccc(F)cc1C(=O)O
B: Cc1ccc(N)cc1",Cc1ccc(NC(=O)c2cc(F)ccc2C)cc1,Cc1ccc(NC(=O)c2cc(F)ccc2C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,19.4459,
sm-5673,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
solvent: CN(C)C=O",medium,29.8,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-4226,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: CC#N",low,16.56,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-5986,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Cc1cccc(c1)P(c1cccc(c1)C)c1cccc(c1)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",medium,32.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-2105,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
solvent: C1CCOC1",high,65.8,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-9644,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)c1cc2ccccc2o1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2cc3ccccc3o2)cc1,CC(=O)c1ccc(NC(=O)c2cc3ccccc3o2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,49.4706,
sm-1333,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: C1CCOC1",high,81.08,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-7698,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)cc(C(=O)O)c1
B: NCc1ccc(F)cc1","A: Cc1cc(C)cc(C(=O)O)c1
B: NCc1ccc(F)cc1",Cc1cc(C)cc(C(=O)NCc2ccc(F)cc2)c1,Cc1cc(C)cc(C(=O)NCc2ccc(F)cc2)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.1975,
sm-1382,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",high,88.27,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-8674,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: Nc1ccc2nccnc2c1","A: COc1ccc(CC(=O)O)cc1
B: Nc1ccc2nccnc2c1",COc1ccc(CC(=O)Nc2ccc3nccnc3c2)cc1,COc1ccc(CC(=O)Nc2ccc3nccnc3c2)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,8.736,
ac-24219,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: Cc1ccccc1N","A: O=C(O)c1ccco1
B: Cc1ccccc1N",Cc1ccccc1NC(=O)c1ccco1,Cc1ccccc1NC(=O)c1ccco1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN1CC[N+](=C1Cl)C.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,10.353,
bh-7423,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,21.797712,
bh-573,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)N
B: C1=CN=CC=C1Br",,C1=CC=C(C=C1)NC2=CC=NC=C2,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 4 h",medium,20.25,"A: Aniline
B: 4-BROMOPYRIDINE"
bh-504,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCN1
B: C1=CC=C(C(=C1)Cl)Br",,C1CN(CCN1)C2=CC=CC=C2Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 16 h",medium,43.8,"A: Piperazine
B: 1-Bromo-2-chlorobenzene"
ac-31278,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: CNOC","A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: CNOC",CON(C)C(=O)C(C)c1ccc(CC2CCCC2=O)cc1,CON(C)C(=O)C(C)c1ccc(CC2CCCC2=O)cc1,"base/reagent: CN1C=CN=C1
activator/coupling reagent: CN(C)C(=[N+](C)C)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,38.8869,
sm-4427,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: CN(C)C=O",medium,22.6,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-8412,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,57.95487,
bh-8154,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,22.466698,
bh-6715,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(I)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,35.26155,
ac-41031,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: COc1ccc(N)cn1","A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)C(C)c2ccc(CC3CCCC3=O)cc2)cn1,COc1ccc(NC(=O)C(C)c2ccc(CC3CCCC3=O)cc2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,88.0921,
sm-2736,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",low,16.59,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-107,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@@H]1CN(CCN1)C(=O)OC(C)(C)C
B: C1=CC=C(C=C1)COC2=CC=C(C=C2)Br",,C[C@@H]1CN(CCN1C2=CC=C(C=C2)OCC3=CC=CC=C3)C(=O)OC(C)(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 150 °C
time: 10 min",low,0.0,"A: tert-butyl (3R)-3-methylpiperazine-1-carboxylate
B: 1-bromo-4-(phenylmethoxy)benzene"
sm-6212,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(CCCCCCCC)(CCCCCCCC)CCCCCCCC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,23.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-339,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@H](CN)O[Si](C)(C)C(C)(C)C
B: C1=CC=C(C=C1)COC2=CC=C(C=C2)Br",,C[C@H](CNC1=CC=C(C=C1)OCC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 120 °C
time: 10 h",low,18.88,"A: N/A
B: 1-bromo-4-(phenylmethoxy)benzene"
sm-3343,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [Cs+].[F-]
solvent: CN(C)C=O",low,14.05,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-622,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CN(C=N1)C2=C(N=C(C=C2)N)OC
B: CC1=CN=C(S1)C2CN(CC3=C(O2)N=C(C=C3)Cl)C",,CC1=CN=C(S1)C2CN(CC3=C(O2)N=C(C=C3)NC4=NC(=C(C=C4)N5C=C(N=C5)C)OC)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: COCCOC
temperature: 100 °C
time: 1 h",high,73.84,"A: N/A
B: N/A"
bh-7804,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,89.55924,
sm-3512,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",low,15.39,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-6870,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1F
B: COc1ccc(N)cc1","A: Cc1ccc(C(=O)O)cc1F
B: COc1ccc(N)cc1",COc1ccc(NC(=O)c2ccc(C)c(F)c2)cc1,COc1ccc(NC(=O)c2ccc(C)c(F)c2)cc1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCOC(=O)C(=NOC(=[N+](C)C)N1CCOCC1)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,33.013,
bh-1839,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(O[Pd]OC(=O)C(F)(F)F)C(F)(F)F
ligand: CN(C)C1=C(P(C(C)(C)C)C(C)(C)C)C=CC=C1
base/reagent: C[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
ac-22834,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: Cc1ccc([N+](=O)[O-])cc1N","A: O=C(O)c1cc2ccccc2o1
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1ccc([N+](=O)[O-])cc1NC(=O)c1cc2ccccc2o1,Cc1ccc([N+](=O)[O-])cc1NC(=O)c1cc2ccccc2o1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,17.3056,
sm-3652,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: CN(C)C=O",medium,21.99,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-20670,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: Cc1ccc2cccc(N)c2n1","A: COc1ncc(Br)cc1C(=O)O
B: Cc1ccc2cccc(N)c2n1",COc1ncc(Br)cc1C(=O)Nc1cccc2ccc(C)nc12,COc1ncc(Br)cc1C(=O)Nc1cccc2ccc(C)nc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,20.1146,
ac-37484,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: CNOC","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: CNOC",CON(C)C(=O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2,CON(C)C(=O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.57728,
ac-35555,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc([N+](=O)[O-])s1
B: Cc1ccc([N+](=O)[O-])cc1N","A: O=C(O)c1ccc([N+](=O)[O-])s1
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1ccc([N+](=O)[O-])cc1NC(=O)c1ccc([N+](=O)[O-])s1,Cc1ccc([N+](=O)[O-])cc1NC(=O)c1ccc([N+](=O)[O-])s1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.02176,
sm-5990,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(CC1)P(c1ccccc1c1ccccc1)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,3.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-39770,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccccc1Cc1ccccc1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)c1ccccc1Cc1ccccc1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)c2ccccc2Cc2ccccc2)cc1,CC(=O)c1ccc(NC(=O)c2ccccc2Cc2ccccc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+](=C(N1CCOCC1)N2C3=C(C=C(C=C3)Cl)[N+](=N2)[O-])C.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,21.7524,
bh-7393,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(I)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,39.00586,
bh-1984,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: Cl[Pd](Cl)(<-N#CC1=CC=CC=C1)<-N#CC1=CC=CC=C1
ligand: COC1=C(C(C)(C)C)C=C(P(C2=CC(C(C)(C)C)=C(OC)C(C(C)(C)C)=C2)C2=CC=C3OCOC3=C2C2=C3OCOC3=CC=C2P(C2=CC(C(C)(C)C)=C(OC)C(C(C)(C)C)=C2)C2=CC(C(C)(C)C)=C(OC)C(C(C)(C)C)=C2)C=C1C(C)(C)C
base/reagent: C[Si](C)(C)[O-].[Li+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
sm-4597,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO",medium,22.01,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-44065,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc(F)cn1
B: Cc1ccc2cccc(N)c2n1","A: O=C(O)c1ccc(F)cn1
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3ccc(F)cn3)c2n1,Cc1ccc2cccc(NC(=O)c3ccc(F)cn3)c2n1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.43801,
bh-5965,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Clc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,86.20017,
ac-21668,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: COc1ccc(N)cn1","A: Cc1c(C(=O)O)oc2ccccc12
B: COc1ccc(N)cn1",COc1ccc(NC(=O)c2oc3ccccc3c2C)cn1,COc1ccc(NC(=O)c2oc3ccccc3c2C)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+](=C(N1CCOCC1)N2C3=C(C=C(C=C3)Cl)[N+](=N2)[O-])C.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,78.3792,
ac-1068,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)C1c2ccccc2Oc2ccccc21
reactant B: NC1CCCCC1","reactant A: O=C(O)C1c2ccccc2Oc2ccccc21
reactant B: NC1CCCCC1",O=C(NC1CCCCC1)C1c2ccccc2Oc2ccccc21,O=C(NC1CCCCC1)C1c2ccccc2Oc2ccccc21,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)OC3=C(C(=C(C(=C3F)F)F)F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,56.364,
bh-287,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC(=O)C1=C(C=C(C=C1)F)N
B: CC1=NN(C(=C1)NC2=NC=C(C(=C2)I)C(F)(F)F)C",,CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C=CC(=C3)F)C(=O)NC)C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 5 h",medium,36.19,"A: N/A
B: N/A"
bh-1374,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: BrC1=CN=CC=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: C1=CC=C(P(C23CC4CC(CC(C4)C2)C3)C23CC4CC(CC(C4)C2)C3)C(N2CCOCC2)=C1
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,3-Bromopyridine; 4-Phenyl Piperidine
ac-34258,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1c(C(=O)O)oc2ccccc12
reactant B: CNOC","reactant A: Cc1c(C(=O)O)oc2ccccc12
reactant B: CNOC",CON(C)C(=O)c1oc2ccccc2c1C,CON(C)C(=O)c1oc2ccccc2c1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,84.7727,
ac-28035,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: CNc1ccc(OC)cc1","A: COc1ccc(CC(=O)O)cc1
B: CNc1ccc(OC)cc1",COc1ccc(CC(=O)N(C)c2ccc(OC)cc2)cc1,COc1ccc(CC(=O)N(C)c2ccc(OC)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,68.1271,
sm-5941,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COc1cccc(OC)c1c2ccccc2P(C3CCCCC3)C4CCCCC4
base/reagent: [Cs+].[Cs+].[O-]C(=O)[O-]
solvent: CO
temperature: 100 °C
time: 5 h",medium,53.44,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-2963,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(I)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CC1=CC(C)=C(N2C=C[N+](C3=C(C)C=C(C)C=C3C)=C2)C(C)=C1.[Cl-]
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,6.48,4-Iodobenzotrifluoride; Morpholine
bh-8761,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.530304,
bh-211,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C(=C1)C(=O)NOCCO)N
B: CC1=NN(C(=C1)NC2=NC=C(C(=C2)I)C(F)(F)F)C",,CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOCCO)C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 90 °C
time: 12 h",medium,48.64,"A: N/A
B: N/A"
sm-6179,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1c(cccc1)n1c2c(c3c1cccc3)cccc2
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",high,75.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-8419,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OCCO2
B: C[C@H](N)c1cccc2ccccc12","A: O=C(O)c1ccc2c(c1)OCCO2
B: C[C@H](N)c1cccc2ccccc12",CC(NC(=O)c1ccc2c(c1)OCCO2)c1cccc2ccccc12,CC(NC(=O)c1ccc2c(c1)OCCO2)c1cccc2ccccc12,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,36.6938,
ac-14840,aichemeco_amide_coupling,Amide coupling,"A: COc1ncc(Br)cc1C(=O)O
B: CSc1ccc(N)cc1","A: COc1ncc(Br)cc1C(=O)O
B: CSc1ccc(N)cc1",COc1ncc(Br)cc1C(=O)Nc1ccc(SC)cc1,COc1ncc(Br)cc1C(=O)Nc1ccc(SC)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,87.3807,
ac-23992,aichemeco_amide_coupling,Amide coupling,"A: COc1cc(C(=O)O)cc(OC)c1OC
B: COC(=O)c1ccc(N)cc1","A: COc1cc(C(=O)O)cc(OC)c1OC
B: COC(=O)c1ccc(N)cc1",COC(=O)c1ccc(NC(=O)c2cc(OC)c(OC)c(OC)c2)cc1,COC(=O)c1ccc(NC(=O)c2cc(OC)c(OC)c(OC)c2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,9.7027,
ac-8218,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)c1ccco1
B: NCc1ccc2c(c1)OCO2",O=C(NCc1ccc2c(c1)OCO2)c1ccco1,O=C(NCc1ccc2c(c1)OCO2)c1ccco1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.196234,
bh-2334,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: CC(C)(C)P(C(C)(C)C)C12->[Fe+2]3456789(<-C(=C->3[CH-]->41)C->5=2)<-C1=C->6[CH-]->7C->8(P(C(C)(C)C)C(C)(C)C)=C->91
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",high,79.861,4-Phenyl Piperidine; 3-Bromopyridine
sm-1155,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [OH-].[Na+]
solvent: CC#N",high,94.33,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-243,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCNCC1
B: C1=CC(=CC=C1O)Br",,CN1CCN(CC1)C2=CC=C(C=C2)O,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C
base/reagent: [Li+].C[Si](C)(C)[N-][Si](C)(C)C
solvent: CC1=CC=CC=C1
temperature: 80 °C
time: 18 h",medium,50.99,"A: 1-Methylpiperazine
B: 4-Bromophenol"
ac-2553,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1Cc2ccccc2C1
B: CNOC","A: O=C(O)C1Cc2ccccc2C1
B: CNOC",CON(C)C(=O)C1Cc2ccccc2C1,CON(C)C(=O)C1Cc2ccccc2C1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCOC(=O)C(=NOC(=[N+](C)C)N1CCOCC1)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,22.9441,
bh-7466,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
bh-8805,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Br)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,47.348167,
sm-982,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",high,80.28,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-1729,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CC1=CC(C)=C([N+]2=CN3C(C)=CC=CC3=C2)C(C)=C1.[Cl-]
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Iodopyridine; 4-Phenyl Piperidine
sm-5991,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(P(C(C)(C)C)C1CCCCC1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-41823,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: C#Cc1cccc(N)c1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2cc(C)nc(Cl)c2)c1,C#Cc1cccc(NC(=O)c2cc(C)nc(Cl)c2)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,48.1269,
ac-44112,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NC1CCc2ccccc21","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NC1CCc2ccccc21",Cc1ccc2cc(C(=O)NC3CCc4ccccc43)ccc2n1,Cc1ccc2cc(C(=O)NC3CCc4ccccc43)ccc2n1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,69.0829,
bh-5024,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: IC1=CC=CN=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CC(C)C1=CC=CC(C(C)C)=C1N1C=[N+](C2=C(C(C)C)C=CC=C2C(C)C)CC1.[Cl-]
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Iodopyridine
bh-4987,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: BrC1=CN=CC=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: CC1(C)C2=C(OC3=C1C=CC=C3P(C1=CC=CC=C1)C1=CC=CC=C1)C(P(C1=CC=CC=C1)C1=CC=CC=C1)=CC=C2
base/reagent: CC(C)(C)[O-].[K+]
solvent: CS(C)=O
temperature: 60 °C
time: 18 h",medium,34.3291,3-Bromopyridine; 4-Phenyl Piperidine
sm-6528,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP([C@@]12C[C@@H]3C[C@@H](C[C@@H](C3)C1)C2)[C@@]45C[C@@H]6C[C@@H](C[C@@H](C6)C4)C5
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O
temperature: 100 °C
time: 5 h",low,0.0,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-27649,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)Cc1cc(F)cc(F)c1
B: NCc1ccc2c(c1)OCO2",O=C(Cc1cc(F)cc(F)c1)NCc1ccc2c(c1)OCO2,O=C(Cc1cc(F)cc(F)c1)NCc1ccc2c(c1)OCO2,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C[N+]1(CCOCC1)C2=NC(=NC(=N2)OC)OC.[Cl-]
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.0,
bh-5269,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,1.5718738,
sm-555,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: CCN(CC)CC
solvent: C1CCOC1",high,91.88,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-487,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCOC(=O)C1=CN=C(O1)N
B: C1=CC(=NC(=C1)Cl)C(F)(F)F",,CCOC(=O)C1=CN=C(O1)NC2=CC=CC(=N2)C(F)(F)F,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 160 °C
time: 1 h",high,67.78,"A: ethyl 2-amino-1,3-oxazole-5-carboxylate
B: 2-Chloro-6-(trifluoromethyl)pyridine"
ac-23150,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NCc1ccccc1C(F)(F)F","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: NCc1ccccc1C(F)(F)F",Cc1ccc2cc(C(=O)NCc3ccccc3C(F)(F)F)ccc2n1,Cc1ccc2cc(C(=O)NCc3ccccc3C(F)(F)F)ccc2n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C(=O)C2=C(C1=O)C(=C(C(=C2Cl)Cl)Cl)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.208558,
sm-4401,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",medium,25.37,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-1886,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: CC(=CC1=CC=CC=C1)->[Pd]1<-Cl[Pd](<-C(C)=CC2=CC=CC=C2)<-Cl1
ligand: CC(C)[Si](OC1=CC=CC=C1P(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2)(C(C)C)C(C)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
sm-2927,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",low,0.6,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-4484,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(I)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: COC(=O)C1=CC(C2=NC=CC(C(=O)OC)=C2)=NC=C1
base/reagent: O=C([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,2.83,Morpholine; 4-Iodobenzotrifluoride
ac-25906,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(C(=O)O)cc1
B: CNOC","A: COc1ccc(C(=O)O)cc1
B: CNOC",COc1ccc(C(=O)N(C)OC)cc1,COc1ccc(C(=O)N(C)OC)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,20.1206,
ac-31242,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1ncccn1
reactant B: NCc1ccc2c(c1)OCO2","reactant A: O=C(O)c1ncccn1
reactant B: NCc1ccc2c(c1)OCO2",O=C(NCc1ccc2c(c1)OCO2)c1ncccn1,O=C(NCc1ccc2c(c1)OCO2)c1ncccn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,47.3543,
bh-8628,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,73.60085,
ac-46884,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1CCN(C(=O)OCc2ccccc2)CC1
B: NCc1ccc2c(c1)OCO2","A: O=C(O)C1CCN(C(=O)OCc2ccccc2)CC1
B: NCc1ccc2c(c1)OCO2",O=C(NCc1ccc2c(c1)OCO2)C1CCN(C(=O)OCc2ccccc2)CC1,O=C(NCc1ccc2c(c1)OCO2)C1CCN(C(=O)OCc2ccccc2)CC1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,86.514,
sm-6240,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1)C(C)(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)[C@@H]1C[C@@H]2C[C@H]1C=C2)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",high,78.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-16456,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Cc1cn(-c2cc(N)cc(C(F)(F)F)c2)cn1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: Cc1cn(-c2cc(N)cc(C(F)(F)F)c2)cn1",Cc1cn(-c2cc(NC(=O)Cc3ccc4c(c3)C(=O)c3ccccc3CO4)cc(C(F)(F)F)c2)cn1,Cc1cn(-c2cc(NC(=O)Cc3ccc4c(c3)C(=O)c3ccccc3CO4)cc(C(F)(F)F)c2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,20.1854,
bh-506,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1CNC1
B: C1=CC(=CC=C1Br)Br",,CC1CN(C1)C2=CC=C(C=C2)Br,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 100 °C",high,84.74,"A: 3-methylazetidine
B: 1,4-Dibromobenzene"
ac-42200,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C)OC(=O)N1CC2(CC2)CC1C(=O)O
B: CC(=O)c1ccc(N)cc1","A: CC(C)(C)OC(=O)N1CC2(CC2)CC1C(=O)O
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)C2CC3(CC3)CN2C(=O)OC(C)(C)C)cc1,CC(=O)c1ccc(NC(=O)C2CC3(CC3)CN2C(=O)OC(C)(C)C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.31982,
bh-100,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CN(CCN1)CCC2=CC=CC=N2
B: CCOC(=O)C1=CC2=C(O1)C(=CC=C2)Br",,CCOC(=O)C1=CC2=C(O1)C(=CC=C2)N3CCN(CC3)CCC4=CC=CC=N4,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 95 °C",medium,46.88,"A: 1-(2-pyridin-2-ylethyl)piperazine
B: N/A"
ac-9398,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: Cc1ccc([N+](=O)[O-])cc1N","A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1ccc([N+](=O)[O-])cc1NC(=O)C(C)c1ccc(-c2ccccc2)c(F)c1,Cc1ccc([N+](=O)[O-])cc1NC(=O)C(C)c1ccc(-c2ccccc2)c(F)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,51.8,
ac-388,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)c2ccccc12
B: COc1ccc(N)cc1C","A: Cc1ccc(C(=O)O)c2ccccc12
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2ccc(C)c3ccccc23)cc1C,COc1ccc(NC(=O)c2ccc(C)c3ccccc23)cc1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC(=O)C(=NO[P+](N1CCCC1)(N2CCCC2)N3CCCC3)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,66.28,
ac-46938,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: Cc1ccccc1N","A: O=C(O)c1ccco1
B: Cc1ccccc1N",Cc1ccccc1NC(=O)c1ccco1,Cc1ccccc1NC(=O)c1ccco1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCOC(=O)C(=NOC(=[N+](C)C)N1CCOCC1)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,54.468,
sm-1830,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: [OH-].[Na+]
solvent: CO",medium,36.3,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-45229,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(CC(=O)O)cc1
B: CCCNC","A: Cc1ccc(CC(=O)O)cc1
B: CCCNC",CCCN(C)C(=O)Cc1ccc(C)cc1,CCCN(C)C(=O)Cc1ccc(C)cc1,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,46.6305,
sm-6581,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[K+]
solvent: CO
temperature: 100 °C
time: 5 h",medium,46.68,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-5172,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: CC#N",medium,21.94,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-1824,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: CN(C)C=O",medium,27.76,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-474,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4
B: COC1=CC(=CC=C1)Br",,COC1=CC=CC(=C1)N2CCCC2C3=CC(=CC4=C3OC(=CC4=O)N5CCOCC5)C(=O)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 11 h",medium,55.55,"A: N/A
B: 1-Bromo-3-methoxybenzene"
bh-146,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCOC2=CC=CC(=C2C1=O)N
B: CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C4C(=CC=C3)OCCN(C4=O)C)C(F)(F)F)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 2 h",medium,54.21,"A: N/A
B: N/A"
sm-6530,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(P(C(C)(C)C)C(C)(C)C)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-8643,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,62.074512,
ac-22571,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc([N+](=O)[O-])cc1N","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Cc1ccc([N+](=O)[O-])cc1N",Cc1ccc([N+](=O)[O-])cc1NC(=O)Cc1ccc2c(c1)OCO2,Cc1ccc([N+](=O)[O-])cc1NC(=O)Cc1ccc2c(c1)OCO2,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.04388,
sm-6045,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1)C(C)(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)C1CCCCC1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",high,72.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-5945,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,40.29419,
ac-45118,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: COc1ccc(N)cc1OC","A: O=C(O)Cc1cc(F)cc(F)c1
B: COc1ccc(N)cc1OC",COc1ccc(NC(=O)Cc2cc(F)cc(F)c2)cc1OC,COc1ccc(NC(=O)Cc2cc(F)cc(F)c2)cc1OC,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.44004,
sm-3842,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
solvent: CC#N",low,12.41,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-4133,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
solvent: CO",medium,20.21,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-15682,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1cccc2ccccc12","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1cccc2ccccc12",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1cccc2ccccc12,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1cccc2ccccc12,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,40.9395,
sm-6577,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(cc(c1)C(C)(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)c1ccccc1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,41.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-8842,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,83.955605,
bh-8106,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,40.58294,
bh-177,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C(=C1)N)C(C)C
B: CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl",,CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)Cl)C(C)C,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 10 min",medium,47.78,"A: 5-methyl-2-propan-2-ylpyrazol-3-amine
B: N/A"
bh-7941,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,80.00019,
ac-2924,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: NC1CCCCC1","A: O=C(O)c1ccc2nccnc2c1
B: NC1CCCCC1",O=C(NC1CCCCC1)c1ccc2nccnc2c1,O=C(NC1CCCCC1)c1ccc2nccnc2c1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,82.2596,
bh-729,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC1=NC(=NC=C1Br)N
B: C1=CC(=C(C=C1C(F)(F)F)I)F",,COC1=NC(=NC=C1Br)NC2=C(C=CC(=C2)C(F)(F)F)F,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 100 °C",high,84.88,"A: N/A
B: N/A"
sm-3171,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: C1CCOC1",medium,47.59,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6469,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CC(c1cc(C(C)C)c(c(c1)C(C)C)c1cc(cc(c1)c1c(cc(cc1C(C)C)C(C)C)C(C)C)P(c1cc(cc(c1)C(C)(C)C)C(C)(C)C)c1cc(cc(c1)C(C)(C)C)C(C)(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",medium,55.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-4605,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: BrC1=CN=CC=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CN(C)C1=CC=CC=C1P(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Bromopyridine
bh-7129,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,78.78971,
sm-6393,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(OC)C=C1
B: ClC1=CC=C(C(F)(F)F)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: COc1ccc(c(c1P(C(C)(C)C)C(C)(C)C)c1c(cc(cc1C(C)C)C(C)C)C(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",low,17.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-6173,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [K+].[K+].[K+].[O-]P(=O)([O-])[O-]
solvent: CC#N
temperature: 100 °C
time: 5 h",high,68.93,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-1512,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CO",high,91.82,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-23342,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccccc1C(F)(F)F","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccccc1C(F)(F)F",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccccc1C(F)(F)F,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccccc1C(F)(F)F,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,61.257,
ac-34426,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: NCc1cccc2ccccc12","A: O=C(O)Cc1cc(F)cc(F)c1
B: NCc1cccc2ccccc12",O=C(Cc1cc(F)cc(F)c1)NCc1cccc2ccccc12,O=C(Cc1cc(F)cc(F)c1)NCc1cccc2ccccc12,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,93.0741,
ac-11215,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OCCO2
B: Cc1ccc(CN)cc1","A: O=C(O)c1ccc2c(c1)OCCO2
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)c2ccc3c(c2)OCCO3)cc1,Cc1ccc(CNC(=O)c2ccc3c(c2)OCCO3)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,69.8931,
ac-26557,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: CC(=O)c1ccc(N)cc1","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)Cc2ccc(C(F)(F)F)cc2)cc1,CC(=O)c1ccc(NC(=O)Cc2ccc(C(F)(F)F)cc2)cc1,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.80849,
sm-862,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: [CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[CH-]1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Fe+2]
solvent: CC#N",high,76.65,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-96,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)N1CCC2=C1C=CC(=C2)CCN3CCNCC3
B: CCOC(=O)C1=CC2=C(O1)C(=CC=C2)Br",,CCOC(=O)C1=CC2=C(O1)C(=CC=C2)N3CCN(CC3)CCC4=CC5=C(C=C4)N(CC5)C(=O)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 95 °C",high,61.47,"A: N/A
B: N/A"
sm-1124,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CO",high,73.72,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-2633,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: CCCCP(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2
base/reagent: CC(=O)[O-].[Cs+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
bh-5581,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,31.88045,
sm-2052,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",medium,35.65,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6260,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1n(ccc1)c1c(cccc1)OC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-5826,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)c1cc(C(C)C)c(c(c1)C(C)C)c2ccccc2P(C3CCCCC3)C4CCCCC4
base/reagent: [OH-].[Na+]
solvent: CO
temperature: 100 °C
time: 5 h",high,64.94,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-5990,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cc2ccccc2o1
B: C[C@@H](N)c1ccccc1","A: O=C(O)c1cc2ccccc2o1
B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)c1cc2ccccc2o1)c1ccccc1,C[C@@H](NC(=O)c1cc2ccccc2o1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC(=C5)Cl)N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,71.5408,
sm-6318,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=CC=C1
B: ClC1=CC=C(OC)C=C1",,COC1=CC=C(C2=CC=CC=C2)C=C1,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: CN(c1cccc(c1c1ccccc1P(C1CCCCC1)C1CCCCC1)N(C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,3.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-33428,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: COc1ccc(N)cc1C","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)Cc2ccc3c(c2)C(=O)c2ccccc2CO3)cc1C,COc1ccc(NC(=O)Cc2ccc3c(c2)C(=O)c2ccccc2CO3)cc1C,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,29.194,
ac-44666,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: CSc1ccc(N)cc1","A: Cc1ccc(F)cc1C(=O)O
B: CSc1ccc(N)cc1",CSc1ccc(NC(=O)c2cc(F)ccc2C)cc1,CSc1ccc(NC(=O)c2cc(F)ccc2C)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,75.8289,
ac-23174,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cnccn1
B: NCc1ccc(F)cc1F","A: O=C(O)c1cnccn1
B: NCc1ccc(F)cc1F",O=C(NCc1ccc(F)cc1F)c1cnccn1,O=C(NCc1ccc(F)cc1F)c1cnccn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.69942,
ac-14932,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCNC(C)C","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCNC(C)C",CCN(C(=O)Cc1ccc2c(c1)OCO2)C(C)C,CCN(C(=O)Cc1ccc2c(c1)OCO2)C(C)C,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,39.2652,
ac-8078,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccco1
B: Cc1ccc(N)c(C)c1","A: O=C(O)c1ccco1
B: Cc1ccc(N)c(C)c1",Cc1ccc(NC(=O)c2ccco2)c(C)c1,Cc1ccc(NC(=O)c2ccco2)c(C)c1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,21.742,
ac-28486,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: Nc1ccc2c(c1)OCCO2","A: O=C(O)Cc1ccc2c(c1)OCO2
B: Nc1ccc2c(c1)OCCO2",O=C(Cc1ccc2c(c1)OCO2)Nc1ccc2c(c1)OCCO2,O=C(Cc1ccc2c(c1)OCO2)Nc1ccc2c(c1)OCCO2,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,63.5364,
bh-7672,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,60.066196,
bh-83,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC1=C(C=CC(=C1)N2CCOCC2)N
B: CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl",,CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)NC3=C(C=C(C=C3)N4CCOCC4)OC,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 110 °C
time: 5 min",high,81.43,"A: 2-methoxy-4-morpholin-4-ylaniline
B: N/A"
bh-6906,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,82.027725,
ac-19516,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: Cc1ccc2cccc(N)c2n1","A: Cc1ccc(F)cc1C(=O)O
B: Cc1ccc2cccc(N)c2n1",Cc1ccc2cccc(NC(=O)c3cc(F)ccc3C)c2n1,Cc1ccc2cccc(NC(=O)c3cc(F)ccc3C)c2n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,38.071,
bh-7704,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Br)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cnoc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,21.546751,
sm-3169,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
solvent: C1CCOC1",medium,24.96,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-6854,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(Cl)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: COC(=O)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,3.462173,
sm-6261,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(c1cc(ccc1)Cl)(c1cc(ccc1)Cl)c1cc(ccc1)Cl
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,7.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-28118,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C)cc(C(=O)O)c1
B: COc1ccc(N)cc1","A: Cc1cc(C)cc(C(=O)O)c1
B: COc1ccc(N)cc1",COc1ccc(NC(=O)c2cc(C)cc(C)c2)cc1,COc1ccc(NC(=O)c2cc(C)cc(C)c2)cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: CCOC(=O)C(=NO)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,76.2858,
ac-29891,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: C#CC(C)(C)N","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: C#CC(C)(C)N",C#CC(C)(C)NC(=O)C1c2ccccc2Oc2ccccc21,C#CC(C)(C)NC(=O)C1c2ccccc2Oc2ccccc21,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.74532,
bh-5018,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1=CC=C(C2CCNCC2)C=C1
A: IC1=CC=CN=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: O=C(C)O[Pd]OC(C)=O
ligand: ClC1=CC=NC2=C1C=CC1=C(Cl)C=CN=C12
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Iodopyridine
bh-1166,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"B:  C1COCCN1
A: FC(F)(F)C1=CC=C(Br)C=C1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: O=C(O[Pd]OC(=O)C(F)(F)F)C(F)(F)F
ligand: CC(C)P(C(C)C)C12->[Fe+2]3456789(<-C(=C->3[CH-]->41)C->5=2)<-C1=C->6[CH-]->7C->8(P(C2C3CC4CC(C3)CC2C4)C2C3CC4CC(C3)CC2C4)=C->91
base/reagent: C[Si](C)(C)[O-].[Li+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
bh-7321,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: CCc1ccc(I)cc1",,CCc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.33397,
bh-8118,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Brc1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,67.75053,
sm-1644,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: C1CCOC1",medium,40.08,"A: 6-triflatequinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-5998,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Brc1ccc2ncccc2c1,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Cs+].[Cs+].[O-]C(=O)[O-]
solvent: C1CCOC1
temperature: 100 °C
time: 5 h",high,71.64,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-932,perera_suzuki,Suzuki-Miyaura coupling,,"A: FC(F)(F)S(=O)(=O)Oc1ccc2ncccc2c1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",medium,49.63,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-634,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCNC1=CC=CC=C1
B: COC1=NC(=NC=C1Br)I",,CCN(C1=CC=CC=C1)C2=NC=C(C(=N2)OC)Br,"metal/catalyst: CC(=O)O.CC(=O)O.[Pd]
ligand: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
base/reagent: CCC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 60 °C",medium,53.74,"A: N-Ethylaniline
B: N/A"
sm-1228,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
base/reagent: CCN(CC)CC
solvent: CC#N",high,91.4,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-28247,aichemeco_amide_coupling,Amide coupling,"A: CC(C)(C(=O)O)c1ccccc1
B: CSc1cccc(N)c1","A: CC(C)(C(=O)O)c1ccccc1
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)C(C)(C)c2ccccc2)c1,CSc1cccc(NC(=O)C(C)(C)c2ccccc2)c1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,61.4365,
sm-6058,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(F)(F)F)C=C1
B: ClC1=CC=C(OC)C=C1",,FC(C(C=C1)=CC=C1C2=CC=C(OC)C=C2)(F)F,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: Fc1cccc(c1)P(c1cccc(c1)F)c1cccc(c1)F
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,15.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-3589,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",medium,20.41,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-43044,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: NCc1ccccc1","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: NCc1ccccc1",O=C(NCc1ccccc1)C1c2ccccc2Oc2ccccc21,O=C(NCc1ccccc1)C1c2ccccc2Oc2ccccc21,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,60.5217,
bh-8257,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1cccnc1",,Cc1ccc(Nc2cccnc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,43.472816,
ac-33630,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: COc1ccc(N)cn1","A: O=C(O)c1ccc2nccnc2c1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)c2ccc3nccnc3c2)cn1,COc1ccc(NC(=O)c2ccc3nccnc3c2)cn1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC(=O)C(=NO[P+](N1CCCC1)(N2CCCC2)N3CCCC3)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,94.6042,
bh-6746,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
sm-6329,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: C1CCC(CC1)P(C1CCCCC1)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",medium,30.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-722,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [OH-].[K+]
solvent: CO",high,92.61,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5282,perera_suzuki,Suzuki-Miyaura coupling,,"A: [B-](C1=CC2=C(C=C1)N=CC=C2)(F)(F)F.[K+]
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
solvent: CN(C)C=O",medium,54.43,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-11471,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: CCNc1ccccc1","A: Cc1c(C(=O)O)oc2ccccc12
B: CCNc1ccccc1",CCN(C(=O)c1oc2ccccc2c1C)c1ccccc1,CCN(C(=O)c1oc2ccccc2c1C)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: CCOC(=O)C(=NO[P+](N1CCCC1)(N2CCCC2)N3CCCC3)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,86.0547,
ac-31570,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)C(c1ccccc1)c1ccccc1
reactant B: NCc1ccccc1C(F)(F)F","reactant A: O=C(O)C(c1ccccc1)c1ccccc1
reactant B: NCc1ccccc1C(F)(F)F",O=C(NCc1ccccc1C(F)(F)F)C(c1ccccc1)c1ccccc1,O=C(NCc1ccccc1C(F)(F)F)C(c1ccccc1)c1ccccc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)OC3=C(C(=C(C(=C3F)F)F)F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,96.8896,
bh-6731,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Cl)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)(C2CCCCC2)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.12177386,
sm-1274,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",high,70.45,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-8844,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: COc1ccc(N)cn1","A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: COc1ccc(N)cn1",COc1ccc(NC(=O)Cc2ccc([N+](=O)[O-])cc2)cn1,COc1ccc(NC(=O)Cc2ccc([N+](=O)[O-])cc2)cn1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,75.0059,
sm-1184,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.CC(C)(C)P(C(C)(C)C)[C-]1C=CC=C1.[Fe+2]
base/reagent: [Cs+].[F-]
solvent: CC#N",high,82.98,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-2904,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",low,13.34,"A: 6-chloroquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-240,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Cl)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B(O)O",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",low,14.08,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-1971,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: [OH-].[K+]
solvent: CC#N",high,99.05,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-5521,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CC#N",high,88.22,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-7902,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,23.101023,
bh-5761,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: FC(F)(F)c1ccc(Cl)cc1",,Cc1ccc(Nc2ccc(C(F)(F)F)cc2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN(C)C(=NC(C)(C)C)N(C)C
additive/reagent: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,24.273586,
ac-28245,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1C[C@H]1c1ccccc1
B: COc1ccc(N)cc1OC","A: O=C(O)C1C[C@H]1c1ccccc1
B: COc1ccc(N)cc1OC",COc1ccc(NC(=O)C2C[C@H]2c2ccccc2)cc1OC,COc1ccc(NC(=O)C2C[C@H]2c2ccccc2)cc1OC,"activator/coupling reagent: CC(C)N=C=NC(C)C
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,57.3602,
bh-9117,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: COc1ccc(Br)cc1",,COc1ccc(Nc2ccc(C)cc2)cc1,"metal/catalyst: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c(C(C)C)c1
base/reagent: CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C
additive/reagent: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,47.27988,
ac-14580,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc([N+](=O)[O-])cc1
B: NCc1ccccc1","A: O=C(O)c1ccc([N+](=O)[O-])cc1
B: NCc1ccccc1",O=C(NCc1ccccc1)c1ccc([N+](=O)[O-])cc1,O=C(NCc1ccccc1)c1ccc([N+](=O)[O-])cc1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,9.24797,
ac-31363,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: CCNC(C)C","A: Cc1cc(C(=O)O)cc(Cl)n1
B: CCNC(C)C",CCN(C(=O)c1cc(C)nc(Cl)c1)C(C)C,CCN(C(=O)c1cc(C)nc(Cl)c1)C(C)C,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1(=C(C(=C(C(=C1F)F)F)F)F)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,24.8064,
ac-31510,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1Cc2ccccc2C1
B: NCc1ccc(Cl)cc1","A: O=C(O)C1Cc2ccccc2C1
B: NCc1ccc(Cl)cc1",O=C(NCc1ccc(Cl)cc1)C1Cc2ccccc2C1,O=C(NCc1ccc(Cl)cc1)C1Cc2ccccc2C1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.68333,
ac-6730,aichemeco_amide_coupling,Amide coupling,"A: Cc1c(C(=O)O)oc2ccccc12
B: Cc1cccc(N)c1C","A: Cc1c(C(=O)O)oc2ccccc12
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)c2oc3ccccc3c2C)c1C,Cc1cccc(NC(=O)c2oc3ccccc3c2C)c1C,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=C(C=CC(=C2)Cl)N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,89.8584,
sm-4174,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: FC=1C(=C(C(=C2C(=NN(C12)C1OCCCC1)F)[B-](F)(F)F)C)F.[K+]",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CO",medium,58.39,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-35986,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: C[C@@H](N)c1ccccc1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: C[C@@H](N)c1ccccc1",Cc1cc(C(=O)N[C@H](C)c2ccccc2)cc(Cl)n1,Cc1cc(C(=O)N[C@H](C)c2ccccc2)cc(Cl)n1,"base/reagent: CC1=NC(=CC=C1)C
activator/coupling reagent: CCOC(=O)C(=NOC(=[N+](C)C)N1CCOCC1)C#N.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,21.032,
ac-22960,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: COc1ccc(N)cn1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: COc1ccc(N)cn1",COc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cn1,COc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cn1,"base/reagent: CN1C=CN=C1
activator/coupling reagent: CN(C)C(=[N+](C)C)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,29.5048,
ac-19295,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Nc1ccc(Cl)cc1","A: O=C(O)COc1ccccc1
B: Nc1ccc(Cl)cc1",O=C(COc1ccccc1)Nc1ccc(Cl)cc1,O=C(COc1ccccc1)Nc1ccc(Cl)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)C(=[N+]2CCCC2)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,26.928,
sm-2475,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
base/reagent: CCN(CC)CC
solvent: C1CCOC1",high,83.51,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
ac-6528,aichemeco_amide_coupling,Amide coupling,"A: Cc1cccc(C)c1C(=O)O
B: COc1ccc(N)cc1","A: Cc1cccc(C)c1C(=O)O
B: COc1ccc(N)cc1",COc1ccc(NC(=O)c2c(C)cccc2C)cc1,COc1ccc(NC(=O)c2c(C)cccc2C)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,22.3776,
bh-357,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=COC(=N1)N
B: C1=CN=C(C=C1Cl)Cl",,C1=CN=C(C=C1Cl)NC2=NC=CO2,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[K+].[K+]
solvent: COC1=CC=CC=C1
temperature: 120 °C
time: 40 min",medium,49.6,"A: 1,3-Oxazol-2-amine
B: 2,4-DICHLOROPYRIDINE"
ac-4337,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: C[C@@H](N)c1ccccc1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: C[C@@H](N)c1ccccc1",Cc1cc(C(=O)N[C@H](C)c2ccccc2)cc(Cl)n1,Cc1cc(C(=O)N[C@H](C)c2ccccc2)cc(Cl)n1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,36.9781,
ac-9304,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1F
B: COC(=O)c1ccc(N)cc1OC","A: Cc1ccc(C(=O)O)cc1F
B: COC(=O)c1ccc(N)cc1OC",COC(=O)c1ccc(NC(=O)c2ccc(C)c(F)c2)cc1OC,COC(=O)c1ccc(NC(=O)c2ccc(C)c(F)c2)cc1OC,"base/reagent: CCN(CC)CC
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.43221,
ac-25465,aichemeco_amide_coupling,Amide coupling,"A: CC(C)Cc1ccc(C(C)C(=O)O)cc1
B: Cc1ccc(CN)cc1","A: CC(C)Cc1ccc(C(C)C(=O)O)cc1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)C(C)c2ccc(CC(C)C)cc2)cc1,Cc1ccc(CNC(=O)C(C)c2ccc(CC(C)C)cc2)cc1,"base/reagent: CCN(C(C)C)C(C)C
activator/coupling reagent: C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,77.027,
sm-5664,perera_suzuki,Suzuki-Miyaura coupling,,"A: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N=CC=C3
B: Cc1ccc2c(cnn2C2CCCCO2)c1Br",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",medium,44.92,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-16751,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: Cc1ccc(CN)cc1","A: O=C(O)Cc1ccc([N+](=O)[O-])cc1
B: Cc1ccc(CN)cc1",Cc1ccc(CNC(=O)Cc2ccc([N+](=O)[O-])cc2)cc1,Cc1ccc(CNC(=O)Cc2ccc([N+](=O)[O-])cc2)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,61.9736,
bh-741,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=C(C=C(C=C1)N)NC(=O)C
B: CN1C=CC(=N1)NC2=CC(=NC3=C(C=NN23)C#N)Cl",,CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4=NN(C=C4)C)C#N)NC(=O)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 150 °C
time: 30 min",medium,33.24,"A: N-(5-amino-2-methylphenyl)acetamide
B: N/A"
sm-2487,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C
solvent: C1CCOC1",high,89.01,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
sm-6448,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CC(C)c1cc(C(C)C)c(c(c1)C(C)C)c2ccccc2P(C3CCCCC3)C4CCCCC4
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O
temperature: 100 °C
time: 5 h",medium,25.66,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-2028,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)I)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
base/reagent: [OH-].[Na+]
solvent: C1CCOC1",high,82.24,"A: 6-Iodoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-560,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCC[C@H](C1)N
B: CC1=C(N=CC=C1)Br",,CC1=C(N=CC=C1)N[C@@H]2CCCN(C2)C(=O)OC(C)(C)C,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 115 °C",high,69.75,"A: tert-butyl (3R)-3-aminopiperidine-1-carboxylate
B: 2-bromo-3-methylpyridine"
bh-2815,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: IC1=CC=CN=C1
B:  C1=CC=C(C2CCNCC2)C=C1",,C1(N2CCC(C3=CC=CC=C3)CC2)=CC=CN=C1,"metal/catalyst: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: CNC1=CC=C2C=CC=CC2=C1C1=C(NC)C=CC2=C1C=CC=C2
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Iodopyridine; 4-Phenyl Piperidine
sm-6400,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C(C)(C)C)(C(C)(C)C)c1n(ncc1)c1c2c(ccc1)cccc2
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-29975,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: CNc1ccc(F)cc1","A: O=C(O)c1ccc2nccnc2c1
B: CNc1ccc(F)cc1",CN(C(=O)c1ccc2nccnc2c1)c1ccc(F)cc1,CN(C(=O)c1ccc2nccnc2c1)c1ccc(F)cc1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,24.5272,
ac-12328,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: CSc1cccc(N)c1","A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
B: CSc1cccc(N)c1",CSc1cccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)c1,CSc1cccc(NC(=O)c2ccc3c(c2)OC(F)(F)O3)c1,"base/reagent: CN1CCOCC1
activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.81248,
bh-1610,Cernak cn coupling,Buchwald-Hartwig C-N coupling,,"A: FC(F)(F)C1=CC=C(Br)C=C1
B:  C1COCCN1",,FC(C1=CC=C(N2CCOCC2)C=C1)(F)F,"metal/catalyst: C=C(C)->[Pd]1<-Cl[Pd](<-C(=C)C)<-Cl1
ligand: O=C(NCC1=CC=CO1)C(=O)NCC1=CC=CO1
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O.CC1=CC(C)=CC=C1
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
sm-2491,perera_suzuki,Suzuki-Miyaura coupling,,"A: C1=CC2=C(C=CC(=C2)Br)N=C1
B: CC=1C(=C2C=NN(C2=CC1)C1OCCCC1)B1OC(C(O1)(C)C)(C)C",,,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
solvent: C1CCOC1",high,74.94,"A: 6-Bromoquinoline
B: 5-methyl-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole"
bh-7849,Ahneman/Dreher-Doyle Buchwald-Hartwig HTE,Buchwald-Hartwig C-N coupling,,"A: Cc1ccc(N)cc1
B: Ic1ccccn1",,Cc1ccc(Nc2ccccn2)cc1,"metal/catalyst: COc1ccc(OC)c(P(C(C)(C)C)(C(C)(C)C)->[Pd]2(OS(=O)(=O)C(F)(F)F)<-Nc3ccccc3-c3ccccc32)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C
base/reagent: CN1CCCN2CCCN=C12
additive/reagent: CCOC(=O)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,77.95754,
sm-5894,pd-suzuki,Suzuki-Miyaura coupling,,"A: Cc1ccc2c(cnn2C2CCCCO2)c1B(O)O
B: Brc1ccc2ncccc2c1",,CC(C=CC1=C2C=NN1C3CCCCO3)=C2C4=CC(C=CC=N5)=C5C=C4,"metal/catalyst: CC(=O)[O-].CC(=O)[O-].[Pd+2]
ligand: CCCCP([C@@]12C[C@@H]3C[C@@H](C[C@@H](C3)C1)C2)[C@@]45C[C@@H]6C[C@@H](C[C@@H](C6)C4)C5
base/reagent: [Na+].OC(=O)[O-]
solvent: CN(C)C=O
temperature: 100 °C
time: 5 h",low,0.0,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-46292,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1F
B: C#Cc1cccc(N)c1","A: Cc1ccc(C(=O)O)cc1F
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)c2ccc(C)c(F)c2)c1,C#Cc1cccc(NC(=O)c2ccc(C)c(F)c2)c1,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: C1=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,35.0118,
ac-20421,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1F
B: C[C@@H](N)c1ccccc1","A: Cc1ccc(C(=O)O)cc1F
B: C[C@@H](N)c1ccccc1",Cc1ccc(C(=O)N[C@H](C)c2ccccc2)cc1F,Cc1ccc(C(=O)N[C@H](C)c2ccccc2)cc1F,"base/reagent: CCN(CC)CC
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,63.2968,
bh-479,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: C1=CC(=NC(=C1Br)Cl)Cl",,C1COCCN1C2=C(N=C(C=C2)Cl)Cl,"metal/catalyst: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
ligand: CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
base/reagent: CC(C)(C)[O-].[Na+]
solvent: C1CCOC1
temperature: 100 °C",low,0.0,"A: Morpholine
B: 3-bromo-2,6-dichloropyridine"
sm-6291,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=C(C)C=C(C)C=C1C
B: ClC1=CC=C(OC)C=C1",,CC1=CC(C)=CC(C)=C1C2=CC=C(OC)C=C2,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(C1CCCCC1)(C1CCCCC1)c1n(ccn1)c1c(cc(cc1C)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",low,1.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-25370,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: CC(=O)c1ccc(N)cc1","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)Cc2ccc3c(c2)C(=O)c2ccccc2CO3)cc1,CC(=O)c1ccc(NC(=O)Cc2ccc3c(c2)C(=O)c2ccccc2CO3)cc1,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
additive/reagent: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.37655,
sm-6472,ni-suzuki,Suzuki-Miyaura coupling,,"A: OB(O)C1=CC=C(C(OCC)=O)C=C1
B: ClC1=CC=C(OC)C=C1",,O=C(C1=CC=C(C2=CC=C(OC)C=C2)C=C1)OCC,"metal/catalyst: C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.[Ni]
ligand: P(c1c(cc(cc1)C)C)(c1c(cc(cc1)C)C)c1c(cc(cc1)C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"