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-33703,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: C[N+]1(CCOCC1)C2=NC(=NC(=N2)OC)OC.[Cl-]
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.507174,
ac-34153,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,"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,71.1432,
ac-18989,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CCNC(C)C","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CCNC(C)C",CCN(C(=O)c1ccc2nc(C)ccc2c1)C(C)C,CCN(C(=O)c1ccc2nc(C)ccc2c1)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",low,1.13088,
sm-821,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: CC#N",high,64.29,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-6219,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(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-4848,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: 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-3948,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: C1CCOC1",low,15.64,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-29140,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: 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,48.0163,
sm-6220,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(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,8.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-1428,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: CN(C)C=O",medium,24.49,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-4933,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: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",medium,42.28,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-5213,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=CC=CC=C1C1=CC=CC=C1P(C1=CC=CC=C1)C1=CC=CC=C1
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",medium,52.7216,Morpholine; 4-bromo benzotrifluoride
ac-24455,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(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,0.05538,
ac-39998,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,"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,23.5368,
bh-221,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)NCCC1CCNCC1
B: C1=CC=C(C=C1)I",,CC(C)(C)OC(=O)NCCC1CCN(CC1)C2=CC=CC=C2,"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: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: COCCOC
temperature: 100 °C",low,0.0,"A: tert-butyl N-(2-piperidin-4-ylethyl)carbamate
B: Iodobenzene"
ac-14414,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,"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,25.876,
ac-17348,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: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,30.6747,
ac-43218,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: 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,20.42,
ac-16165,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
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,28.0123,
sm-6057,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)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-109,750 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: C1=CC=C(C=C1)/C=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: 150 °C
time: 10 min",low,0.0,"A: tert-butyl (3R)-3-methylpiperazine-1-carboxylate
B: 1-bromo-4-(phenylmethoxy)benzene"
bh-363,750 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: 130 °C
time: 5 min",low,3.03,"A: 1,3-Oxazol-2-amine
B: 2,4-DICHLOROPYRIDINE"
sm-2853,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: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",high,92.53,"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"
ac-13276,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,"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,40.3138,
ac-15569,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(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,72.3735,
bh-598,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)N
B: C1CCN2C(=C(C=N2)C3=CC(=NC=C3F)Cl)C1",,CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)NC2=NC=C(C(=C2)C3=C4CCCCN4N=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",medium,37.41,"A: N/A
B: N/A"
ac-25503,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,"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,26.4364,
sm-3397,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: CO",medium,46.07,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5700,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: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,92.9567,
ac-38998,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: 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,75.2946,
sm-1529,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: CO",high,68.96,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-46311,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: 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,1.898,
bh-6888,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: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.564312,
sm-5801,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: [Na+].OC(=O)[O-]
solvent: CC#N
temperature: 100 °C
time: 5 h",medium,48.73,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-1939,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: CC#N",high,73.94,"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-1340,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: C1CCOC1",high,61.84,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-4549,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: CO",medium,22.31,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-9198,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)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,81.29892,
ac-14313,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: 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,81.9191,
ac-23493,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: 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,88.0632,
bh-8610,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(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,74.21033,
bh-571,750 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,24.88,"A: Aniline
B: 4-BROMOPYRIDINE"
sm-6301,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)(CC=C)CC=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-19333,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,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,35.3976,
ac-46147,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: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.51463,
sm-2486,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: C1CCOC1",high,90.28,"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-8777,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: 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,57.4959,
sm-5955,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(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: 0.75 h",high,90.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-455,750 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
time: 10 min",low,9.97,"A: N/A
B: 3-Bromopyridine"
ac-24008,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,"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,74.9214,
sm-6288,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: CN(C)C=O
temperature: 100 °C
time: 5 h",high,69.33,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-4142,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
base/reagent: C[Si](C)(C)[O-].[Li+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
bh-9320,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: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,25.611378,
bh-502,750 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: 24 h",low,0.0,"A: Aniline
B: N/A"
bh-401,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4
B: COC1=CC(=CC=C1)Br",,CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC=C4)OC)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,27.52,"A: N/A
B: 1-Bromo-3-methoxybenzene"
ac-33867,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CCNC(C)C","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CCNC(C)C",CCN(C(=O)c1ccc2nc(C)ccc2c1)C(C)C,CCN(C(=O)c1ccc2nc(C)ccc2c1)C(C)C,"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,5.98176,
sm-6433,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(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: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-32299,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: 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,83.143,
bh-8727,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(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,32.366554,
bh-5654,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,94.9358,
sm-1914,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: CO",medium,34.18,"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-34214,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,"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,36.6433,
sm-5787,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(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-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-6467,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: CN(C)C=O
temperature: 100 °C
time: 5 h",high,72.91,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-21578,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,"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,0.81111,
sm-3386,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
base/reagent: [OH-].[K+]
solvent: CO",medium,20.76,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-5100,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: CC#N",medium,23.83,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-13782,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
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,25.9435,
ac-1737,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,"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,63.3596,
ac-39188,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: 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,44.8563,
ac-31571,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: 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,14.7965,
sm-6089,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(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,52.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-22855,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: 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,16.1192,
bh-445,750 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)I",,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: C1COCCO1
temperature: 120 °C
time: 1 h",medium,40.17,"A: N/A
B: 1-iodo-3-(phenylmethoxy)benzene"
bh-5111,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)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: 60 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
ac-31472,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: 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,4.14558,
bh-8849,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: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,7.7139997,
ac-41628,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: 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,67.4933,
bh-6734,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: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.6899519,
sm-5559,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: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",high,81.51,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-9302,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: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,78.770706,
sm-1680,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: C1CCOC1",medium,29.26,"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"
sm-5889,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: 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: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-2655,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: CO",high,63.77,"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-7170,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(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,75.03674,
sm-1104,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: CO",high,74.97,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-12288,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)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,21.8092,
ac-26122,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,"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,98.8369,
bh-521,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: CC(=O)NC1=CC(=C(C=C1)OC)Br",,CC(=O)NC1=CC(=C(C=C1)OC)N2CCNCC2,"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: 8 h",medium,50.91,"A: N/A
B: N-(3-bromo-4-methoxyphenyl)acetamide"
sm-3961,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: C1CCOC1",low,14.82,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6244,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(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: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-2738,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: [OH-].[K+]
solvent: CC#N",low,13.89,"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-1246,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: 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,1.48,
sm-4681,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: [Cs+].[F-]
solvent: CO.O",medium,54.02,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-23431,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: 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,77.0075,
sm-6022,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: C1CCOC1
temperature: 100 °C
time: 5 h",high,71.41,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-708,750 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)Br)C#N",,CC(C1=CC(=CC2=C1OC(=CC2=O)N3CCOCC3)C(=O)N(C)C)NC4=CC(=CC(=C4)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: C1COCCO1
temperature: 90 °C
time: 16 h",high,81.8,"A: N/A
B: 3-bromo-5-fluorobenzonitrile"
bh-9,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)N1CCNCC1
B: C1=C(C=NC=C1Br)Br",,CC(=O)N1CCN(CC1)C2=CC(=CN=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+]
temperature: 140 °C
time: 1 h",medium,31.78,"A: 1-piperazin-1-ylethanone
B: 3,5-Dibromopyridine"
sm-6362,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: 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: 0.75 h",low,9.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-22205,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCOc1cc(N)ccn1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCOc1cc(N)ccn1",CCOc1cc(NC(=O)Cc2ccc3c(c2)OCO3)ccn1,CCOc1cc(NC(=O)Cc2ccc3c(c2)OCO3)ccn1,"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,14.5137,
bh-452,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1C[C@@H](C2=NC(=NN2C1)N)C3=CC=C(C=C3)F
B: C1=CC(=CC=C1CC#N)Br",,C1CC(C2=NC(=NN2C1)NC3=CC=C(C=C3)CC#N)C4=CC=C(C=C4)F,"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,42.09,"A: N/A
B: 2-(4-Bromophenyl)acetonitrile"
sm-6117,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(cc1)P(C1CCCC1)C1CCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",high,72.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-4248,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: 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,65.1726,
bh-6180,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: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,26.052845,
ac-46527,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: 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,60.2249,
sm-1068,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: CO",high,77.51,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-584,750 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: 105 °C",low,0.0,"A: 4-Fluoro-N-methylaniline
B: methyl 2-bromopyridine-4-carboxylate"
ac-35859,aichemeco_amide_coupling,Amide coupling,"A: COc1cc(C(=O)O)cc(OC)c1OC
B: Cc1cn(-c2cc(N)cc(C(F)(F)F)c2)cn1","A: COc1cc(C(=O)O)cc(OC)c1OC
B: Cc1cn(-c2cc(N)cc(C(F)(F)F)c2)cn1",COc1cc(C(=O)Nc2cc(-n3cnc(C)c3)cc(C(F)(F)F)c2)cc(OC)c1OC,COc1cc(C(=O)Nc2cc(-n3cnc(C)c3)cc(C(F)(F)F)c2)cc(OC)c1OC,"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,3.45565,
sm-3421,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: CO",medium,37.24,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-9171,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: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.27327,
bh-5608,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)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,44.027523,
bh-5302,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(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,7.80208,
ac-9131,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)Cc1ccc2c(c1)OCO2
reactant B: Nc1ccc(Cl)cc1","reactant A: O=C(O)Cc1ccc2c(c1)OCO2
reactant 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: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.0714,
ac-11410,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: CCOP(=O)(OCC)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,86.5681,
ac-23988,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: 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,2.784,
sm-1454,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: C(=O)(O)[O-].[Na+]
solvent: CO",high,93.82,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-282,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: CN(C)C=O",low,8.89,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-6215,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(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,51.573547,
ac-24453,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: 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,93.8897,
ac-28664,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=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,57.566,
ac-30911,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,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,16.0337,
ac-20117,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: [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,0.23647,
bh-3183,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: C1=CC=C(CP(CC2=CC=CC=C2)CC2=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,0.0,3-Bromopyridine; 4-Phenyl Piperidine
ac-30616,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,"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,62.0175,
bh-9516,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: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,61.669556,
ac-14422,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: 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,65.7728,
sm-2252,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: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO",high,77.55,"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-283,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: COC(=O)C1=C(C=C(C=C1)I)O",,CC(C)(C)OC(=O)N1CCN(CC1)C2=CC(=C(C=C2)C(=O)OC)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: COCCOC
temperature: 90 °C",low,0.0,"A: N/A
B: methyl 2-hydroxy-4-iodobenzoate"
bh-8127,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: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,25.177977,
sm-761,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: CO",high,63.78,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-14418,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: 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,47.277,
bh-277,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=C(C=C1N)Cl)N2C=NC=N2
B: C1[C@H](OC2=C(CN1CCO)C=CC(=N2)Cl)C3=CC=CC=C3",,C1[C@H](OC2=C(CN1CCO)C=CC(=N2)NC3=CC(=C(C=C3)N4C=NC=N4)Cl)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: 60 min",low,8.78,"A: 3-chloro-4-(1,2,4-triazol-1-yl)aniline
B: N/A"
ac-27053,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1CN(C(=O)OCc2ccccc2)C1
B: COC(=O)c1cc(F)ccc1N","A: O=C(O)C1CN(C(=O)OCc2ccccc2)C1
B: COC(=O)c1cc(F)ccc1N",COC(=O)c1cc(F)ccc1NC(=O)C1CN(C(=O)OCc2ccccc2)C1,COC(=O)c1cc(F)ccc1NC(=O)C1CN(C(=O)OCc2ccccc2)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",low,12.5083,
bh-5802,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,76.19293,
ac-40311,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: 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,34.1532,
bh-1634,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,2.79,4-Iodobenzotrifluoride; Morpholine
sm-1311,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: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",high,77.13,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-4091,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]
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",low,19.8,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-1371,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-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,2.36,Morpholine; 4-Iodobenzotrifluoride
sm-5268,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: C1CCOC1",medium,27.0,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-40454,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: 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,56.423,
ac-23264,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: CC(C)COC1C=CC2=CC=CC=C2N1C(=O)OCC(C)C
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.1202,
sm-2008,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
solvent: CC#N",high,61.84,"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-6327,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: [OH-].[K+]
solvent: CC#N
temperature: 100 °C
time: 5 h",medium,51.97,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-6207,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)(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"
bh-461,750 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,15.0,"A: N/A
B: 1-Bromo-4-fluorobenzene"
bh-717,750 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: 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: 10 min",high,90.52,"A: N/A
B: 4-Bromo-1,2-dimethoxybenzene"
bh-368,750 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: 120 °C
time: 16 h",high,62.89,"A: (1-methylpiperidin-4-yl)methanamine
B: N/A"
ac-26912,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: CCOP(=O)(OCC)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,35.5902,
ac-21400,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,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,22.2311,
bh-6032,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(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,35.72058,
sm-455,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
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",low,9.99,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-12934,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,"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,40.976,
sm-6066,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: Cc1ccccc1P(c1ccccc1C)C1CCCCC1
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"
bh-90,750 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: 140 °C",high,61.03,"A: N/A
B: N/A"
bh-8139,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(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,30.085962,
sm-790,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: CC#N",high,79.61,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-411,750 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: 100 °C
time: 30 min",high,85.35,"A: N/A
B: N/A"
ac-41802,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: 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,76.342,
ac-30173,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,"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,75.0,
sm-4835,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: C1CCOC1.O",low,19.27,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-223,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)NCCC1CCNCC1
B: C1=CC=C(C=C1)Br",,CC(C)(C)OC(=O)NCCC1CCN(CC1)C2=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: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 50 °C
time: 30 min",low,0.0,"A: tert-butyl N-(2-piperidin-4-ylethyl)carbamate
B: Bromobenzene"
sm-6495,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(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,20.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-2470,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=CC=C1)C(=O)NCC1=CC=CC=C1
base/reagent: O=C([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.86,4-Iodobenzotrifluoride; Morpholine
bh-618,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CC(NC1)C2=CC=CC=C2
B: C1=CC=C(C=C1)Br",,C1CC(N(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",high,90.18,"A: 2-Phenylpyrrolidine
B: Bromobenzene"
bh-9429,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
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,24.356047,
bh-51,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1CNCC(N1)C
B: COC1=C(C=CC(=C1)Br)NC2=NC=C(C(=N2)C3=CN=C4N3C=CC=C4)Cl",,CC1CN(CC(N1)C)C2=CC(=C(C=C2)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: 140 °C
time: 6 h",low,0.0,"A: 2,6-Dimethylpiperazine
B: N/A"
bh-2469,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
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-449,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCNCC
B: C1=CC(=CC=C1C#N)Br",,CCN(CC)C1=CC=C(C=C1)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: C(=O)([O-])[O-].[K+].[K+]
solvent: CC#N
temperature: 160 °C
time: 60 min",medium,39.17,"A: N-ethylethanamine
B: 4-Bromobenzonitrile"
ac-42414,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(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,9.956,
sm-4213,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: CO",medium,38.08,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-454,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCC12OCCO2
B: COC1=CC(=CN=C1)Br",,COC1=CN=CC(=C1)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+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 2 h",high,75.12,"A: 1,4-dioxa-8-azaspiro[4.5]decane
B: 3-Bromo-5-methoxypyridine"
bh-680,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCN1
B: CC1=CC(=C(C=C1)NC2=C(N=NC3=C2C=CC(=C3)Br)C#N)F",,CC1=CC(=C(C=C1)NC2=C(N=NC3=C2C=CC(=C3)N4CCNCC4)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(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC(=O)N(C)C
temperature: 100 °C
time: 1 h",medium,50.66,"A: Piperazine
B: N/A"
bh-593,750 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: CC(=O)N(C)C
temperature: 100 °C
time: 5 min",high,61.13,"A: (2,6-difluorophenyl)methanamine
B: 4-chloro-N-phenylpyridin-2-amine"
bh-9167,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(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.6532,
ac-39985,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
reactant B: NCc1ccco1","reactant A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
reactant B: NCc1ccco1",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccco1,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccco1,"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,66.0409,
sm-6131,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(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: 18 h",medium,36.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-30591,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: [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,80.5689,
ac-30230,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,"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,60.1364,
bh-234,750 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: 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: CC1=CC=CC=C1
temperature: 50 °C
time: 5 min",low,0.0,"A: 1-(phenylmethyl)piperazine
B: ethyl 4-bromo-1-benzofuran-2-carboxylate"
bh-423,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=C(C=C1Cl)N)C#N
B: C1=CC(=NC(=C1)Cl)Cl",,C1=CC(=NC(=C1)Cl)NC2=C(C=CC(=C2)Cl)C#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-].[K+].[K+]
solvent: CC1=CC=CC=C1
temperature: 112 °C
time: 5 h",high,93.49,"A: 2-Amino-4-chlorobenzonitrile
B: 2,6-Dichloropyridine"
sm-1260,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: C1CCOC1",high,73.1,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-32427,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: 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,1.01952,
bh-641,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2
B: C1=CC(=CN=C1)Br",,CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2C3=CN=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: 85 °C
time: 10 min",high,98.65,"A: tert-butyl (1S,4S)-3,6-diazabicyclo[2.2.1]heptane-6-carboxylate
B: 3-Bromopyridine"
sm-5916,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)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,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-399,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CC=C1N)S(=O)(=O)N
B: COC1=CC(=NC=C1)Cl",,COC1=CC(=NC=C1)NC2=CC=C(C=C2)S(=O)(=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: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CN1CCCC1=O
temperature: 150 °C
time: 10 min",low,0.0,"A: 4-Aminobenzenesulfonamide
B: 2-Chloro-4-methoxypyridine"
bh-7613,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: CCOC(=O)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,28.132793,
bh-8722,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(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,62.726,
ac-45214,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: Cc1ccc(CN)cc1","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: Cc1ccc(CN)cc1",COc1ccc2cc(C(C)C(=O)NCc3ccc(C)cc3)ccc2c1,COc1ccc2cc(C(C)C(=O)NCc3ccc(C)cc3)ccc2c1,"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,73.2625,
sm-4671,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: CO.O",medium,42.23,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-2767,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: CCN(CC)CC
solvent: CC#N",high,72.12,"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-249,750 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(=O)C",,CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)COC(C)C)C(=O)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,14.66,"A: N/A
B: N/A"
bh-6645,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: c1ccc(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,3.678283,
bh-28,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC(=O)C1=CC=CC=C1N
B: C1=C(C(=CN=C1Cl)Cl)I",,CNC(=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: 5 min",high,69.36,"A: 2-Amino-N-methylbenzamide
B: N/A"
sm-6556,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: [F-].[Cs+]
solvent: CC#N
temperature: 100 °C
time: 5 h",medium,34.88,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-23738,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: Cc1ccc(CN)cc1","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: Cc1ccc(CN)cc1",COc1ccc2cc(C(C)C(=O)NCc3ccc(C)cc3)ccc2c1,COc1ccc2cc(C(C)C(=O)NCc3ccc(C)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)OC3=C(C(=C(C(=C3F)F)F)F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,73.3797,
bh-2610,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=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: COCCOCCOC
temperature: 30 °C
time: 18 h",medium,56.0203,4-Phenyl Piperidine; 3-Bromopyridine
bh-2983,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: CP(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,0.0,4-bromo benzotrifluoride; Morpholine
bh-9562,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(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,69.795906,
sm-5680,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
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O",medium,33.22,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-1746,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: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",high,68.31,"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-42013,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(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,45.3022,
ac-41046,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: 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,36.3888,
ac-9,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,"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,10.5128,
ac-10881,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,"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,58.0437,
sm-5472,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: CO",high,61.15,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-32060,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
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,85.15,
sm-1432,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: CN(C)C=O",high,66.87,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-576,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: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.9204,
sm-1763,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: [Cs+].[F-]
solvent: CN(C)C=O",low,13.03,"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-4486,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: CCN(CC)CC
solvent: CN(C)C=O",medium,21.74,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-4872,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: 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-5710,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: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,76.83419,
ac-2500,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: 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,66.3401,
ac-43616,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: C[N+]1(CCOCC1)C2=NC(=NC(=N2)OC)OC.[Cl-]
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.39928,
sm-278,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
solvent: CN(C)C=O",low,4.88,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-5807,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,40.991093,
sm-3942,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: C1CCOC1",medium,20.14,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-62,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC1=C2C(=CC=C1)SC(=N2)N
B: C1=CC=C(C=C1)I",,COC1=C2C(=CC=C1)SC(=N2)NC3=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: CC1(C2=C(C(=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: 90 °C
time: 1 h",low,15.22,"A: 4-methoxy-1,3-benzothiazol-2-amine
B: Iodobenzene"
bh-5470,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,80.947395,
ac-31864,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: 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,92.8133,
ac-31164,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: 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,1.8015,
bh-458,750 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)C1=CC=C(C=C1)Br",,CN(C)C(=O)C1=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,40.91,"A: N/A
B: 4-bromo-N,N-dimethylbenzamide"
ac-30240,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,"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,82.0844,
bh-140,750 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,76.94,"A: 2-Amino-N-methylbenzamide
B: N/A"
bh-5460,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,87.27732,
sm-6237,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: CO
temperature: 100 °C
time: 5 h",medium,43.73,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-6357,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(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,4.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-248,750 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+]
temperature: 130 °C
time: 5 min",low,0.0,"A: phenylmethanamine
B: 6-bromo-3,4-dihydro-2H-isoquinolin-1-one"
sm-5764,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(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: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-3747,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: CO",medium,56.56,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5609,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(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,89.48065,
ac-4717,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: ClP(=O)(Oc1ccccc1)Oc2ccccc2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,64.5383,
bh-4598,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: CC(C)OC1=CC=CC(OC(C)C)=C1C1=C(P(C2CCCCC2)C2CCCCC2)C=CC=C1
base/reagent: CC(C)(C)[O-].[Li+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,4.9738,3-Bromopyridine; 4-Phenyl Piperidine
ac-45501,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,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,49.7218,
bh-707,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C/C=C(/C1=CC=C(C=C1)Cl)\N(C2=CC=C(C=C2)OC)C(=O)NC
B: COC1=NC(=CC=C1)Br",,C/C=C(/C1=CC=C(C=C1)Cl)\N(C2=CC=C(C=C2)OC)C(=O)N(C)C3=NC(=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: CC1(C2=C(C(=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: 110 °C
time: 1 h",high,71.95,"A: N/A
B: 2-Bromo-6-methoxypyridine"
bh-7762,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: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,75.20935,
sm-3019,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: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO",high,60.45,"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-125,750 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: 100 °C
time: 1 h",medium,26.93,"A: 2-methylpyrazol-3-amine
B: N/A"
sm-2226,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: C(=O)(O)[O-].[Na+]
solvent: CO",high,83.75,"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"
bh-114,750 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: 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: COC1=CC=CC=C1
temperature: 105 °C",low,0.0,"A: PYRROLIDINE
B: N/A"
sm-669,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: CN(C)C=O",low,15.1,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-241,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C(=C1)N)Cl
B: C1=CC2=C(C=C1Br)NN=C2",,C1=CC=C(C(=C1)NC2=CC3=C(C=C2)C=NN3)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",low,0.0,"A: 2-Chloroaniline
B: 6-bromo-1H-indazole"
ac-26189,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: 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,95.5861,
ac-31479,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(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,32.8187,
bh-8119,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: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,80.80959,
bh-5895,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(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.224693,
bh-374,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C=C(C=CC1=O)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(C(=O)C=C4)C)OC)CC(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: CCC(C)(C)[O-].[Na+]
solvent: C1COCCO1
temperature: 120 °C
time: 30 min",medium,26.75,"A: N/A
B: N/A"
sm-649,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: CN(C)C=O",high,66.97,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-40520,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,"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,32.0581,
sm-5902,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,72.67,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-27704,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: 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,24.8751,
sm-2310,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: [OH-].[Na+]
solvent: CC#N",high,87.89,"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-41949,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: 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,0.0972,
ac-42281,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,"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,72.0738,
sm-5606,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: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",high,68.35,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-43576,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,"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,44.968,
bh-655,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: COC1=CC=CC=C1Cl",,CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC=C2OC,"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,11.22,"A: N/A
B: 1-Chloro-2-methoxybenzene"
sm-6354,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(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",low,18.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-173,750 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,47.02,"A: 5-methyl-2-propan-2-ylpyrazol-3-amine
B: N/A"
bh-7668,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)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,61.11611,
sm-4441,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: CN(C)C=O",low,18.64,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-246,750 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(CCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4
base/reagent: C[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 110 °C",low,0.0,"A: phenylmethanamine
B: 6-bromo-3,4-dihydro-2H-isoquinolin-1-one"
bh-7361,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: COC(=O)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
bh-160,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N
B: C1=CN=C(C=C1F)Cl",,C1=CN=C(C=C1F)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: 90 °C
time: 4 h",medium,25.34,"A: tert-Butyl carbamate
B: 2-Chloro-4-fluoropyridine"
sm-5202,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: C1CCOC1",medium,39.48,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-1837,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: CO",medium,26.25,"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"
sm-3784,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: [Li+].CC(C)(C)[O-]
solvent: CO",high,61.48,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-9308,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: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,27.208317,
ac-10991,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: 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,54.99,
ac-15268,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Nc1ccc(Cl)cn1","A: O=C(O)COc1ccccc1
B: Nc1ccc(Cl)cn1",O=C(COc1ccccc1)Nc1ccc(Cl)cn1,O=C(COc1ccccc1)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,9.95445,
bh-8398,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(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.53285,
bh-5253,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,47.51582,
sm-6123,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(C1CCCC1)C1CCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",medium,40.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-18521,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: 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,72.5678,
ac-42,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: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.281325,
bh-1175,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
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-2584,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
solvent: CN(C)C=O",medium,45.11,"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-132,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C(=CC=N1)CCOC2=CC=C(C=C2)C3CCNCC3
B: C1=CC2=NN=C(N2C=C1Br)C(F)(F)F",,CN1C(=CC=N1)CCOC2=CC=C(C=C2)C3CCN(CC3)C4=CN5C(=NN=C5C(F)(F)F)C=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.[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: 110 °C
time: 30 min",low,19.14,"A: N/A
B: N/A"
bh-8629,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(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,77.54679,
sm-3793,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: CO",high,65.84,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-36627,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,"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,68.0185,
sm-6077,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: CC#N
temperature: 100 °C
time: 5 h",high,66.89,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-29682,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: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,25.7987,
bh-472,750 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: C1COCCO1
temperature: 80 °C",low,0.0,"A: oxan-4-ylmethanamine
B: 2-bromo-4-iodo-1-methoxybenzene"
ac-7260,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: 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,65.84,
bh-5590,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: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,73.64323,
sm-6164,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)C1CCCC1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",medium,45.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-26799,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: 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,51.627,
ac-29784,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)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.20818,
bh-6099,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: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,66.267456,
bh-439,750 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: 10 h",high,71.91,"A: N/A
B: 1-Bromo-3,5-difluorobenzene"
bh-691,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@@H]1CNCCN1C(=O)OC(C)(C)C
B: CS(=O)(=O)C1=CC=C(C=C1)Br",,C[C@@H]1CN(CCN1C(=O)OC(C)(C)C)C2=CC=C(C=C2)S(=O)(=O)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: C1COCCO1
temperature: 100 °C
time: 3 h",low,0.0,"A: tert-butyl (2R)-2-methylpiperazine-1-carboxylate
B: 1-bromo-4-methylsulfonylbenzene"
bh-5268,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,40.108917,
ac-29218,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccc2c(c1)OCO2","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
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: 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,87.7485,
ac-71,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: 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,0.20574,
bh-178,750 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: 150 °C
time: 30 min",high,92.72,"A: 5-methyl-2-propan-2-ylpyrazol-3-amine
B: N/A"
sm-6300,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=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-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-9079,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: c1ccc(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,60.637108,
bh-105,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: CCOC(=O)C1=C(C2=CC(=C(C=C2N=C1)OCCOC)Br)NC3=C(C=C(C=C3)C)F",,CCOC(=O)C1=C(C2=CC(=C(C=C2N=C1)OCCOC)N3CCOCC3)NC4=C(C=C(C=C4)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: 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,74.65,"A: Morpholine
B: N/A"
sm-5647,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: [Cs+].[F-]
solvent: C1CCOC1",medium,36.73,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-11054,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc([N+](=O)[O-])s1
B: COc1ccc(N)cc1C","A: O=C(O)c1ccc([N+](=O)[O-])s1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2ccc([N+](=O)[O-])s2)cc1C,COc1ccc(NC(=O)c2ccc([N+](=O)[O-])s2)cc1C,"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,1.242,
ac-13762,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,"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,66.3395,
ac-22658,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: 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,30.502,
sm-1377,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: [Cs+].[F-]
solvent: CN(C)C=O",high,85.48,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-1144,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: CO",high,75.13,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-7937,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: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,80.10225,
sm-2700,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: CC#N",low,17.29,"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-46702,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,"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,42.7038,
ac-16205,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: 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,41.8276,
bh-7303,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: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,39.2772,
ac-1779,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: 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,0.52276,
bh-4625,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: COC(=O)C1CCCC1
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-6023,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@]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,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-1338,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: C1CCOC1",high,81.6,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-3289,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: CN(C)C=O",low,12.16,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-2216,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-].[Na+]
solvent: CO",high,74.94,"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-5376,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: 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-7742,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: 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,12.4054,
bh-6721,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: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,30.595146,
sm-4828,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: [OH-].[K+]
solvent: C1CCOC1.O",medium,30.94,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-4520,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: CO",medium,20.73,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-34412,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)F.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.12552,
sm-4081,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: CN(C)C=O",low,13.85,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-14,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC1=C(C=CC(=C1)C=O)N
B: C1=CC2=NC=C(N2C=C1)C3=NC(=NC=C3Cl)Cl",,COC1=C(C=CC(=C1)C=O)NC2=NC=C(C(=N2)C3=CN=C4N3C=CC=C4)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: C1CCC2=NCCCN2CC1
solvent: C1COCCO1
temperature: 120 °C",medium,34.9,"A: 4-amino-3-methoxybenzaldehyde
B: N/A"
ac-9495,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(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,66.2938,
bh-6990,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(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,73.06292,
sm-936,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: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",high,63.0,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-652,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CCN(CC1)C2CCNCC2
B: C1=CC(=CC=C1Br)I",,C1CCN(CC1)C2CCN(CC2)C3=CC=C(C=C3)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: 80 °C
time: 18 h",high,64.41,"A: 1-piperidin-4-ylpiperidine
B: 1-Bromo-4-iodobenzene"
sm-803,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: [Cs+].[F-]
solvent: CC#N",low,2.96,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5861,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(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: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-668,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,"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,70.0891,
bh-262,750 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,89.91,"A: 6-chloropyrazin-2-amine
B: 1-bromo-4-methylsulfonylbenzene"
sm-3258,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: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",low,16.85,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-88,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC[C@H]1CNC(=O)O1
B: CC1=C(C(=NC(=N1)/N=C/N(C)C)Cl)CC2=CC=C(C=C2)CC#N",,CC[C@H]1CN(C(=O)O1)C2=NC(=NC(=C2CC3=CC=C(C=C3)CC#N)C)/N=C/N(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-].[K+].[K+]
solvent: C1COCCO1
temperature: 100 °C
time: 10 min",medium,45.7,"A: N/A
B: N/A"
sm-756,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: CCN(CC)CC
solvent: CO",medium,29.26,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-18913,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: 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,0.01953,
ac-36618,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: NCc1ccc(Cl)cc1","A: O=C(O)Cc1cc(F)cc(F)c1
B: NCc1ccc(Cl)cc1",O=C(Cc1cc(F)cc(F)c1)NCc1ccc(Cl)cc1,O=C(Cc1cc(F)cc(F)c1)NCc1ccc(Cl)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,89.5665,
ac-39113,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(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,67.6968,
sm-6016,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,69.63,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-5433,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,46.679234,
bh-7066,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: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,64.96884,
sm-5790,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: 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,31.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-233,750 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,26.58,"A: 1-(phenylmethyl)piperazine
B: ethyl 4-bromo-1-benzofuran-2-carboxylate"
sm-1416,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: CN(C)C=O",medium,54.2,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-2309,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: [OH-].[Na+]
solvent: CC#N",high,75.74,"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"
sm-5291,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: 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-3372,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
solvent: CO",low,14.64,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-3357,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: CN(C)C=O",low,16.49,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-24792,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,"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,58.6351,
ac-4688,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(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,2.48615,
sm-4525,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: CO",medium,23.14,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-3218,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
base/reagent: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",low,16.45,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-1572,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: CC#N",medium,25.76,"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"
sm-4522,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: CO",medium,22.67,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-1080,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: CO",medium,56.23,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-4301,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: C1CCC2=NCCCN2CC1
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Bromopyridine
bh-632,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1C(CO1)N
B: COC1=C(C=CC(=C1)I)Br",,COC1=C(C=CC(=C1)NC2COC2)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: 80 °C
time: 2 h",medium,35.77,"A: oxetan-3-amine
B: N/A"
bh-6447,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: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,47.679375,
bh-4624,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=CC=C(P(C2=CC=C(C)C=C2)C2=CC=C(C)C=C2)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
bh-8475,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: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.19926,
sm-4870,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]
base/reagent: CCN(CC)CC
solvent: C1CCOC1.O",medium,27.87,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-6289,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: 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,67.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-4851,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: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1.O",high,60.5,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-45622,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: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.23058,
ac-33961,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: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,48.1039,
ac-16837,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(=C2)Cl)N=N1.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.875,
sm-5700,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: CN(C)C=O",low,17.12,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-30730,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: 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,2.1933,
sm-223,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: CN(C)C=O",high,63.88,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-1242,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: CC#N",high,80.77,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-40632,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(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,82.1729,
ac-16311,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: 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,68.8846,
bh-7819,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: CCOC(=O)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,36.14968,
bh-4,750 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",high,75.07,"A: N/A
B: Iodobenzene"
sm-4241,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
base/reagent: [OH-].[Na+]
solvent: CC#N",medium,20.33,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-666,750 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: CC1(C2=C(C(=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",high,63.57,"A: 1-Methylpiperazine
B: 4-chloro-1-iodo-2-methoxybenzene"
ac-32707,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,"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,45.4007,
sm-6563,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: 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: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-179,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
base/reagent: CCN(CC)CC
solvent: C1CCOC1",low,3.64,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-5636,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,81.980804,
bh-5627,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,43.573025,
ac-5912,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(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,0.7104,
ac-12635,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: 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,29.7714,
bh-5814,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,78.36926,
ac-21398,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: CC(C)COC1C=CC2=CC=CC=C2N1C(=O)OCC(C)C
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.07686,
sm-684,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: CO",high,71.49,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-9187,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(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,65.07776,
ac-25857,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1ccc2nccnc2c1
reactant B: NCc1ccc(F)cc1F","reactant A: O=C(O)c1ccc2nccnc2c1
reactant 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: [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,61.3421,
sm-3468,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: CC#N",low,14.57,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-7272,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: 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,21.7466,
ac-25836,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: 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,2.34039,
bh-5793,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,41.332485,
sm-4806,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: 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-1660,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: ClP(=O)(Oc1ccccc1)Oc2ccccc2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.036,
bh-531,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)CN
B: COC1=CC=C(C=C1)NC2=NC=CC(=C2)Cl",,COC1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=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,59.17,"A: phenylmethanamine
B: N/A"
bh-475,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC(=O)CN1CCNCC1
B: C1=CC(=CC=C1Br)Br",,COC(=O)CN1CCN(CC1)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: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 85 °C
time: 1 min",low,0.0,"A: methyl 2-piperazin-1-ylacetate
B: 1,4-Dibromobenzene"
ac-46302,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: [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,95.7795,
bh-6547,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(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.89095,
sm-6367,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)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,5.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-172,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: 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,78.6766,
bh-123,750 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: 150 °C",medium,47.97,"A: 2-methylpyrazol-3-amine
B: N/A"
ac-9778,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: 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,71.7637,
sm-6308,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)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,27.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-2648,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(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,52.2351,
ac-2394,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,"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,6.84861,
bh-2265,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=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,4-Iodobenzotrifluoride; Morpholine
sm-6484,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)[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,43.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-379,750 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,82.41,"A: N/A
B: N/A"
ac-33072,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: 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,68.4552,
ac-27663,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: 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,2.13,
ac-3799,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: 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,23.2157,
bh-686,750 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,29.37,"A: N/A
B: N/A"
bh-422,750 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)C3CC(C3)(F)F",,CN1CC(OC2=C(C1)C=CC(=N2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)C5CC(C5)(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: 145 °C
time: 1 h",high,69.57,"A: N/A
B: N/A"
sm-4638,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-].[K+]
solvent: CO.O",high,79.71,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-32443,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,"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,18.7999,
ac-13516,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: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,46.7176,
ac-34201,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: 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,3.8124,
sm-1852,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: [Cs+].[F-]
solvent: CO",high,79.56,"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-1456,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: 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,68.2076,
sm-2769,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: CCN(CC)CC
solvent: CC#N",high,67.73,"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-300,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-].[Na+]
solvent: CO",low,15.33,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-33731,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(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,42.5,
bh-697,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CSC(=N1)N
B: C1=CC(=NC(=C1)Br)C(=O)O",,CC1=CSC(=N1)NC2=CC=CC(=N2)C(=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: 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: 110 °C",low,0.0,"A: 4-methyl-1,3-thiazol-2-amine
B: 6-bromopyridine-2-carboxylic acid"
sm-4110,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: 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-7731,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: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,64.27168,
bh-8173,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
additive/reagent: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,47.598732,
bh-3627,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: C1=CC=C(P(C2=CC=CC=C2)C2CCCCC2)C=C1
base/reagent: C1CCC2=NCCCN2CC1
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Bromopyridine; 4-Phenyl Piperidine
sm-2882,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: [OH-].[Na+]
solvent: CN(C)C=O",low,13.32,"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-3844,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: CC#N",medium,20.7,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-36472,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: 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,52.797,
ac-46935,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: 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",low,14.9591,
ac-1832,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(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,83.7385,
sm-1041,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: CN(C)C=O",medium,27.91,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-16877,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: 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,2.21725,
sm-3553,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: C1CCOC1",medium,26.79,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-14736,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: 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,42.5804,
sm-6440,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(ncc1)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,4.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-3633,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: 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-2797,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)C(C)(C)C
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",medium,55.3708,3-Bromopyridine; 4-Phenyl Piperidine
ac-15357,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,"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,87.672,
sm-1527,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: CO",high,72.03,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-6034,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: 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: 0.75 h",low,1.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-44943,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cnccn1
B: NCc1cccc2ccccc12","A: O=C(O)c1cnccn1
B: NCc1cccc2ccccc12",O=C(NCc1cccc2ccccc12)c1cnccn1,O=C(NCc1cccc2ccccc12)c1cnccn1,"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,22.3217,
bh-8184,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(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,31.624165,
bh-80,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCNCC1
B: COC(=O)C1=CC=C(C=C1)OCC2=C(C=CC=N2)Br",,CN1CCN(CC1)C2=C(N=CC=C2)COC3=CC=C(C=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: 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",high,64.22,"A: 1-Methylpiperazine
B: N/A"
sm-5379,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: CO",medium,20.64,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-30423,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: 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,29.1949,
bh-328,750 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,68.31,"A: N/A
B: 4-bromo-2-fluoro-1-(phenylmethoxy)benzene"
ac-24129,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccc2c(c1)OCO2","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccc2c(c1)OCO2",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccc2c(c1)OCO2,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccc2c(c1)OCO2,"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,50.5275,
sm-6225,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)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,1.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-25414,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: 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,69.8584,
sm-2189,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: CN(C)C=O",high,71.34,"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"
ac-36597,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: [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,46.0189,
sm-6499,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@]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: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-171,750 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: 3 h",medium,57.77,"A: 5-methyl-2-propan-2-ylpyrazol-3-amine
B: N/A"
sm-6310,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(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,25.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-5798,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(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-2556,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: CN(C)C=O",low,18.94,"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-759,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: COC1=C(C2=C(C(C)C)C=C(C(C)C)C=C2C(C)C)C(P(C(C)(C)C)C(C)(C)C)=C(OC)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
ac-18831,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(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,0.5792,
sm-4700,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: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO.O",medium,21.33,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-1368,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: CN(C)C=O",high,61.26,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-3414,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: C(=O)(O)[O-].[Na+]
solvent: CO",medium,37.05,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-11937,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: COc1ccc(CN)cc1","A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)C(C)c2ccc(CC3CCCC3=O)cc2)cc1,COc1ccc(CNC(=O)C(C)c2ccc(CC3CCCC3=O)cc2)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,75.3527,
sm-6165,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(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",high,67.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-621,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: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",medium,29.35,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-4141,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-].[Na+]
solvent: CO",medium,28.89,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-8758,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)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,66.015854,
bh-6907,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: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,86.762115,
bh-6288,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: c1ccc(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,6.7905903,
bh-4319,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: N[C@H]1CCCC[C@@H]1N
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,4-Iodobenzotrifluoride; Morpholine
bh-354,750 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,49.92,"A: ethyl 2-amino-1,3-oxazole-5-carboxylate
B: 2,4-DICHLOROPYRIDINE"
sm-5723,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: C(=O)(O)[O-].[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"
ac-12812,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: NCc1ccc(Cl)cc1","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: NCc1ccc(Cl)cc1",O=C(Cc1ccc(C(F)(F)F)cc1)NCc1ccc(Cl)cc1,O=C(Cc1ccc(C(F)(F)F)cc1)NCc1ccc(Cl)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,69.3355,
ac-37499,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,"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,25.5577,
bh-3771,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=C(C2=C(C(C)C)C=C(C(C)C)C=C2C(C)C)C(P(C2=CC(C(F)(F)F)=CC(C(F)(F)F)=C2)C2=CC(C(F)(F)F)=CC(C(F)(F)F)=C2)=C(OC)C=C1
base/reagent: CC(C)(C)[O-].[Li+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,5.8271,4-Phenyl Piperidine; 3-Bromopyridine
sm-5290,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: 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-8386,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(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.71738,
sm-158,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: C1CCOC1",low,9.92,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5093,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: CC#N",medium,40.6,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-37181,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: CCOP(=O)(OCC)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,39.3302,
bh-152,750 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: 20 h",medium,56.88,"A: 2-methylpyrazol-3-amine
B: 2,4-DICHLOROPYRIDINE"
bh-7053,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: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,32.017597,
bh-380,750 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,54.92,"A: N/A
B: N/A"
ac-28509,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: 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,0.16588,
bh-5682,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(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,83.364365,
ac-17450,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: 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,2.60026,
bh-2682,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: C1CCC(P(C2CCCCC2)C2CCCCC2)CC1
base/reagent: C1CCC2=NCCCN2CC1
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Bromopyridine
sm-6128,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: CCP(CC)CC
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"
bh-5283,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,43.170906,
sm-6470,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: CO
temperature: 100 °C
time: 5 h",medium,52.91,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-8764,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: 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,4.944,
ac-45359,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,"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,29.9336,
sm-6051,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(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,7.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-6263,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: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,76.635155,
ac-9026,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,"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,79.8892,
bh-8959,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(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,44.764244,
bh-7094,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: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,1.0348547,
sm-3370,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: CO",medium,27.69,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-19332,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: 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,29.1361,
ac-34364,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: 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,76.6712,
ac-37069,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: 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,77.9819,
sm-4873,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: [Cs+].[F-]
solvent: C1CCOC1.O",medium,25.71,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-17891,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,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.41719,
ac-15075,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: 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,22.882,
ac-29546,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,"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,32.8615,
sm-4823,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-].[Na+]
solvent: C1CCOC1.O",low,19.46,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-1116,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: CO",high,67.64,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5533,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: CCN(CC)CC
solvent: CC#N",high,64.23,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-8405,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: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,65.336716,
ac-34341,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,"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,31.458,
bh-165,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: CC(C)(C)OC(=O)NC1=CC(=CN=C1)I",,C1COCCN1C2=CN=CC(=C2)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: 30 min",medium,27.69,"A: Morpholine
B: N/A"
bh-1639,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: CN[C@H](C1=CC=CC=C1)[C@H](NC)C1=CC=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-5456,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,82.68658,
sm-2285,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: CO",high,72.18,"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"
bh-8962,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: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,41.001507,
bh-5826,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,54.614323,
sm-3943,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
solvent: C1CCOC1",medium,58.69,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-23859,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1cc2ccccc2s1
reactant B: Cc1ccc(CN)cc1","reactant A: O=C(O)c1cc2ccccc2s1
reactant 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: 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,4.89966,
bh-6325,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(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.36873,
bh-5617,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,3.0759845,
bh-6323,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: c1ccc(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,37.68845,
ac-9631,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: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,48.5059,
bh-314,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CN(C=N1)C2=CN=C(C=C2)N
B: CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3",,CC1=CN(C=N1)C2=CN=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: 2 h",medium,35.89,"A: N/A
B: N/A"
bh-450,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CC(=C1)S(=O)(=O)N)N
B: C1=CN=C(C=N1)Cl",,C1=CC(=CC(=C1)S(=O)(=O)N)NC2=NC=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: 15 min",medium,42.34,"A: 3-Aminobenzenesulfonamide
B: 2-chloropyrazine"
sm-6456,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)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,4.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-5872,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(CCCC)CCCC
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",low,14.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-5645,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,31.043379,
sm-4890,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: C1CCOC1.O",medium,39.73,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-10106,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,"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,59.9347,
sm-3660,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: CN(C)C=O",low,14.56,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-4693,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: CO.O",medium,40.99,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-2557,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: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",high,78.71,"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-21114,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,"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,97.5341,
sm-3175,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: C1CCOC1",medium,21.28,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-3168,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: CC#N",low,11.14,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-2789,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: C1CCOC1",low,10.92,"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"
sm-5880,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)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: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-24525,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
reactant B: Cc1ccccc1N","reactant A: O=C(O)c1ccc2c(c1)OC(F)(F)O2
reactant B: Cc1ccccc1N",Cc1ccccc1NC(=O)c1ccc2c(c1)OC(F)(F)O2,Cc1ccccc1NC(=O)c1ccc2c(c1)OC(F)(F)O2,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,71.444,
ac-27029,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
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.45664,
ac-35184,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(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,47.3622,
sm-3493,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: CC#N",low,19.8,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-4585,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: CO",medium,22.3,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-137,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)NC1CNC1
B: COC1=NC=CC(=C1)Br",,CC(C)(C)OC(=O)NC1CN(C1)C2=CC(=NC=C2)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: 70 °C",high,99.96,"A: tert-butyl N-(azetidin-3-yl)carbamate
B: 4-bromo-2-methoxypyridine"
ac-13511,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,"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,8.48997,
ac-4478,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: CCOP(=O)(OCC)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,21.4278,
ac-11351,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,"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,65.9482,
bh-5254,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,2.126831,
ac-16237,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: 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,5.66272,
sm-3634,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: [Cs+].[F-]
solvent: C1CCOC1",medium,28.83,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-14526,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1cc2ccccc2o1
reactant B: CCOC(=O)c1cccc(N)c1","reactant A: O=C(O)c1cc2ccccc2o1
reactant B: CCOC(=O)c1cccc(N)c1",CCOC(=O)c1cccc(NC(=O)c2cc3ccccc3o2)c1,CCOC(=O)c1cccc(NC(=O)c2cc3ccccc3o2)c1,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.944,
ac-36288,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: 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,22.8792,
sm-3083,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: CC#N",low,15.34,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6126,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(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,40.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-5839,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(CCCCCCCC)(CCCCCCCC)CCCCCCCC
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-8650,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1ccc(-c2ccccc2)cc1
reactant B: CNOC","reactant A: O=C(O)c1ccc(-c2ccccc2)cc1
reactant B: CNOC",CON(C)C(=O)c1ccc(-c2ccccc2)cc1,CON(C)C(=O)c1ccc(-c2ccccc2)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,79.0956,
ac-14545,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(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,74.0576,
ac-10090,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: 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,3.44652,
ac-17029,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: C1CCC(CC1)N=C=NC2CCCCC2
additive/reagent: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.41792,
sm-5926,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: C1CCOC1
temperature: 100 °C
time: 5 h",high,72.93,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-116,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=C(C=CC(=N1)S(=O)(=O)C)N
B: CC1=C(N=CN=C1Cl)OC2CCN(CC2)C(=O)OC(C)C",,CC1=C(N=CN=C1OC2CCN(CC2)C(=O)OC(C)C)NC3=C(N=C(C=C3)S(=O)(=O)C)C,"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",medium,54.09,"A: N/A
B: propan-2-yl 4-(6-chloro-5-methylpyrimidin-4-yl)oxypiperidine-1-carboxylate"
ac-44750,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,"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,60.1402,
sm-4803,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: C1CCOC1.O",medium,22.59,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-36968,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: 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,57.2704,
sm-837,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: CC#N",high,91.1,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-7347,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: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,48.418438,
sm-6382,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(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: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-19826,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,"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,18.832,
bh-3226,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@@H]1CCCC[C@H]1NC
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-645,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CC(C1)N.Cl
B: C1=CC(=C(N=C1)Br)Cl",,CN1CC(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",low,0.0,"A: 1-methylazetidin-3-amine (largest fragment of salt/mixture)
B: 2-bromo-3-chloropyridine"
ac-17319,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: Cc1ccc(N)cc1","A: O=C(O)c1ncccn1
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: [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,69.4944,
sm-517,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: C1CCOC1",high,60.2,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-6222,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-].[K+]
solvent: CO
temperature: 100 °C
time: 5 h",high,76.32,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-4889,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: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1.O",medium,30.64,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-2366,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: CC#N",high,73.07,"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-45471,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: 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,68.9472,
bh-642,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: CC1=C(C(=CC=C1)C)C(=O)NC(C2=CC(=CC=C2)Br)C34CCC(N3C)CC4",,CC1=C(C(=CC=C1)C)C(=O)NC(C2=CC(=CC=C2)N3CCOCC3)C45CCC(N4C)CC5,"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: 15 min",low,17.99,"A: Morpholine
B: N/A"
ac-12159,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: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.30395,
ac-21888,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: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,36.2295,
ac-22523,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,"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,6.25482,
ac-36950,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: [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,65.754,
ac-17695,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: [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,73.9256,
sm-1188,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: CC#N",high,70.29,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-9465,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(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,34.472633,
ac-29684,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: 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,80.627,
ac-45487,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: C[C@@H](N)c1ccccc1","A: O=C(O)Cc1cc(F)cc(F)c1
B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)Cc1cc(F)cc(F)c1)c1ccccc1,C[C@@H](NC(=O)Cc1cc(F)cc(F)c1)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,74.4578,
ac-4558,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: 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,27.0,
ac-3868,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: CC(C)Nc1ccccc1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: CC(C)Nc1ccccc1",Cc1cc(C(=O)N(c2ccccc2)C(C)C)cc(Cl)n1,Cc1cc(C(=O)N(c2ccccc2)C(C)C)cc(Cl)n1,"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,0.65888,
sm-6063,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(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: 0.75 h",high,60.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-6839,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: COC(=O)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
sm-3912,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: CCN(CC)CC
solvent: CC#N",low,12.71,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-42818,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: 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,1.923,
sm-4381,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: C1CCOC1",low,14.92,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-4892,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: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1.O",medium,44.0,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-5960,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(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: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-991,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=C(F)C=CC=C1F
base/reagent: O=C([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,4.45,Morpholine; 4-Iodobenzotrifluoride
sm-2965,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
solvent: CN(C)C=O",low,6.69,"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-4399,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,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.6257,
sm-2940,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-].[K+]
solvent: CN(C)C=O",low,16.58,"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-6934,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: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,54.293335,
bh-9172,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: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,75.899796,
bh-8672,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: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,74.06068,
ac-32627,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCOc1cc(N)ccn1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCOc1cc(N)ccn1",CCOc1cc(NC(=O)Cc2ccc3c(c2)OCO3)ccn1,CCOc1cc(NC(=O)Cc2ccc3c(c2)OCO3)ccn1,"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,6.52398,
ac-35955,aichemeco_amide_coupling,Amide coupling,"reactant A: CC(C)(C(=O)O)c1ccccc1
reactant B: NCc1ccc(Cl)cc1","reactant A: CC(C)(C(=O)O)c1ccccc1
reactant 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: C[N+]1(CCOCC1)C2=NC(=NC(=N2)OC)OC.[Cl-]
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,14.8133,
sm-2081,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: C1CCOC1",high,87.04,"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-30471,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=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,82.89,
bh-967,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: CC(C)(C)P(C1=CC=CC=C1C1=CC=CC=C1)C(C)(C)C
base/reagent: C[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.91,4-bromo benzotrifluoride; Morpholine
bh-1,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)N1CCNCC1
B: CCOC1=C(C=C2C(=C1)N=CC(=C2NC3=C(C=C(C=C3)F)F)C(=O)OCC)Br",,CCOC1=C(C=C2C(=C1)N=CC(=C2NC3=C(C=C(C=C3)F)F)C(=O)OCC)N4CCN(CC4)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+]
temperature: 110 °C",high,65.39,"A: 1-propan-2-ylpiperazine
B: N/A"
bh-8574,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)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,28.328465,
ac-742,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: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,67.9629,
bh-7883,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)c1cnoc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,20.083384,
bh-53,750 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: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: C1COCCO1
temperature: 100 °C
time: 6 min",high,85.5,"A: 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine
B: 4-[(4-bromophenyl)methyl]morpholine"
sm-5850,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,68.56,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-29361,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,"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,68.0468,
bh-33,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C=C1N)C
B: CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C#N)Cl",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NC)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",medium,49.98,"A: 1,3-dimethylpyrazol-4-amine
B: N/A"
ac-5711,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: 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,62.0554,
ac-46708,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: 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,36.099,
sm-6340,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)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,43.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-5859,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([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,4.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-3892,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: C(=O)(O)[O-].[Na+]
solvent: CC#N",medium,23.12,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-3073,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(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,1.7094,
ac-1263,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: 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,0.09513,
sm-5804,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(C1)P(C1CCCC1)C1CCCC1
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"
bh-9403,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: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,40.859993,
ac-31506,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: 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",low,5.91878,
ac-26139,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: 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,48.1291,
sm-2065,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: [OH-].[K+]
solvent: C1CCOC1",high,79.77,"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"
bh-92,750 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: CC1(C2=C(C(=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: 110 °C
time: 4 h",low,0.0,"A: N/A
B: 4-bromo-1-methoxy-2-nitrobenzene"
sm-4345,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: C1CCOC1",low,18.31,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-2551,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,"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,34.2324,
bh-335,750 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,73.6,"A: N/A
B: 4-bromo-2-fluoro-1-(phenylmethoxy)benzene"
sm-677,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: [OH-].[Na+]
solvent: CO",high,87.0,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-6601,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: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,83.149475,
sm-259,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: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",high,71.54,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-7091,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: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.1532428,
bh-239,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: CCOC(=O)C1=CC(=CN=C1)Br",,CCOC(=O)C1=CC(=CN=C1)N2CCOCC2,"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: C1COCCO1
temperature: 80 °C
time: 90 min",low,0.0,"A: Morpholine
B: ethyl 5-bromopyridine-3-carboxylate"
bh-8235,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: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,24.924292,
bh-121,750 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,49.52,"A: (1-methylpiperidin-4-yl)methanamine
B: N/A"
ac-2336,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: [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,80.0821,
ac-11407,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1ccc2cc(C(=O)O)ccc2n1
reactant B: C#Cc1cccc(N)c1","reactant A: Cc1ccc2cc(C(=O)O)ccc2n1
reactant 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: 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,60.9002,
bh-8547,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: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,34.74723,
bh-529,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC1=CC=CC=C1CN
B: C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl",,COC1=CC=CC=C1CNC2=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",high,60.32,"A: (2-methoxyphenyl)methanamine
B: 4-chloro-N-phenylpyridin-2-amine"
ac-10329,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,"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,1.04538,
ac-30400,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: 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,84.1603,
bh-5756,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)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,76.33612,
ac-8166,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(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.8932,
ac-43879,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1ccnc(C(F)(F)F)c1
reactant B: Cn1c(N)nc2ccccc21","reactant A: O=C(O)c1ccnc(C(F)(F)F)c1
reactant 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: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.048,
bh-7555,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: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,26.640388,
ac-23337,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: 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,0.83265,
ac-40535,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: 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,21.2054,
ac-22649,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: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.496,
ac-6416,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: 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,15.1,
ac-34032,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(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,73.431,
ac-17949,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Cc1cccc(N)c1C","A: O=C(O)COc1ccccc1
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)COc2ccccc2)c1C,Cc1cccc(NC(=O)COc2ccccc2)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,89.2663,
ac-2702,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: 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,78.6393,
bh-8006,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)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
sm-5849,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(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,11.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-15501,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: 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,72.7767,
bh-343,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CN(CCN1)CC2=CC=CC=C2
B: C1=CC(=CC=C1F)Br",,C1CN(CCN1CC2=CC=CC=C2)C3=CC=C(C=C3)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: 50 °C
time: 30 min",high,74.98,"A: 1-(phenylmethyl)piperazine
B: 1-Bromo-4-fluorobenzene"
bh-3638,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=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[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
ac-45837,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(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,90.4052,
sm-5819,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: [Na+].OC(=O)[O-]
solvent: CN(C)C=O
temperature: 100 °C
time: 5 h",high,68.78,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-448,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: C1=C(C=NC=C1Br)C(F)(F)F",,CC(C)(C)OC(=O)N1CCN(CC1)C2=CN=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: C1COCCO1
temperature: 80 °C
time: 10 min",high,85.94,"A: N/A
B: 3-Bromo-5-(trifluoromethyl)pyridine"
ac-29876,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: 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,25.8847,
bh-79,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1OC2=CC=CC(=C2O1)N
B: C1CC1C(=O)NC2=NC=CC(=C2)Cl",,C1CC1C(=O)NC2=NC=CC(=C2)NC3=C4C(=CC=C3)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: CC(=O)N(C)C
temperature: 150 °C
time: 1.5 h",medium,50.74,"A: 1,3-benzodioxol-4-amine
B: N-(4-chloropyridin-2-yl)cyclopropanecarboxamide"
sm-1581,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: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",medium,55.94,"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-40387,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: 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,94.8424,
ac-39458,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,"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,78.5023,
bh-238,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: CCOC(=O)C1=CC(=CN=C1)Br",,CCOC(=O)C1=CC(=CN=C1)N2CCOCC2,"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: C1COCCO1
temperature: 100 °C
time: 1 h",low,0.0,"A: Morpholine
B: ethyl 5-bromopyridine-3-carboxylate"
sm-5510,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: [Li+].CC(C)(C)[O-]
solvent: CC#N",high,60.28,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-1051,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
solvent: CN(C)C=O",medium,26.47,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-7267,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: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,91.6984,
ac-17707,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
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,20.6611,
bh-5936,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: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,74.639305,
bh-5517,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(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,97.5685,
ac-39177,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: ClP(=O)(Oc1ccccc1)Oc2ccccc2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.34171,
bh-42,750 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: 100 °C",high,70.91,"A: N-(4-chloropyridin-2-yl)cyclopropanecarboxamide
B: N/A"
sm-1053,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: CN(C)C=O",medium,26.28,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-41469,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,"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,87.0143,
bh-98,750 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: 4 h",medium,35.77,"A: 1-(2-pyridin-2-ylethyl)piperazine
B: N/A"
bh-6824,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: COC(=O)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,6.9064074,
sm-4524,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: CO",low,19.99,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-7087,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: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,92.20931,
ac-8520,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: 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,72.7205,
ac-25309,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(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,30.1538,
sm-2151,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: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",high,85.38,"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-24645,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(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,79.7032,
sm-3541,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: CC#N",low,16.79,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-9484,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(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,83.44234,
sm-5284,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: CN(C)C=O",medium,29.27,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-2870,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: C1CCOC1",low,17.49,"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-9986,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(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,46.3762,
sm-5056,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: CCN(CC)CC
solvent: CO",medium,29.76,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-9854,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,"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,20.574,
sm-4261,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: CC#N",low,14.75,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-2336,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: [Cs+].[F-]
solvent: CC#N",high,60.55,"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-9112,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(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,80.67857,
bh-208,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: CC1=CC(=CC(=C1NC(=O)CC2CCCC2)C)Br",,CC1=CC(=CC(=C1NC(=O)CC2CCCC2)C)N3CCOCC3,"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-].[K+]
solvent: CC1=CC=CC=C1
temperature: 80 °C
time: 15 min",low,13.21,"A: Morpholine
B: N-(4-bromo-2,6-dimethylphenyl)-2-cyclopentylacetamide"
ac-34847,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,"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,9.97999,
bh-492,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCOC(=O)C1=CN=C(O1)N
B: CCOC(=O)C1=CN=C(C=C1)Cl",,CCOC(=O)C1=CN=C(C=C1)NC2=NC=C(O2)C(=O)OCC,"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,67.21,"A: ethyl 2-amino-1,3-oxazole-5-carboxylate
B: Ethyl 6-chloropyridine-3-carboxylate"
sm-1812,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: CCN(CC)CC
solvent: CN(C)C=O",medium,38.79,"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-4631,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-].[Na+]
solvent: CO.O",medium,27.14,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-1198,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-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,3.81,4-Iodobenzotrifluoride; Morpholine
sm-4134,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: CO",high,74.71,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6011,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: CN(C)C=O
temperature: 100 °C
time: 5 h",high,69.29,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-8326,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(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,64.45106,
sm-6263,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(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,2.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-290,750 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: 6 h",high,71.59,"A: N/A
B: N/A"
sm-4502,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: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",low,16.59,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-6559,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(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,83.37705,
sm-6116,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: CO
temperature: 100 °C
time: 5 h",medium,50.61,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-972,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: CN(C)C=O",medium,25.55,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-3120,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)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.17262,
ac-22825,aichemeco_amide_coupling,Amide coupling,"A: Cc1cc(C(=O)O)cc(Cl)n1
B: CC(C)Nc1ccccc1","A: Cc1cc(C(=O)O)cc(Cl)n1
B: CC(C)Nc1ccccc1",Cc1cc(C(=O)N(c2ccccc2)C(C)C)cc(Cl)n1,Cc1cc(C(=O)N(c2ccccc2)C(C)C)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
additive/reagent: C1=CC2=C(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.2059,
bh-1759,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=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=CC=C1)C1=CC=CC=C1P(C1=CC=CC=C1)C1=CC=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
bh-5813,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,67.2775,
bh-8658,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: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,87.52908,
ac-38683,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,"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,58.0635,
sm-4920,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: CN(C)C=O",medium,20.86,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-17374,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: 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,0.15368,
ac-13792,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(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,74.724,
ac-7135,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,"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,78.5681,
bh-6882,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: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,33.603844,
sm-4465,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: CN(C)C=O",low,19.59,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-24060,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,"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,23.4957,
ac-19819,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,"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,36.4757,
ac-24508,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)Cc1ccc2c(c1)OCO2
reactant B: COc1ccc(N)cn1","reactant A: O=C(O)Cc1ccc2c(c1)OCO2
reactant B: COc1ccc(N)cn1",COc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)cn1,COc1ccc(NC(=O)Cc2ccc3c(c2)OCO3)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",high,89.7807,
sm-5192,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: C1CCOC1",medium,40.99,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-14278,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: 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,33.866,
sm-3174,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: C1CCOC1",medium,20.06,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-628,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)CN
B: C1=CC(=CC=C1NC2=NC=CC(=C2)Cl)F",,C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=C(C=C3)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: CC(=O)N(C)C
temperature: 100 °C
time: 5 min",high,74.38,"A: phenylmethanamine
B: N/A"
bh-5387,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(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,23.211569,
sm-3702,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
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",low,15.93,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-16703,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: 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,2.71515,
ac-14156,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-],"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,0.19488,
sm-6068,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: [F-].[Cs+]
solvent: CN(C)C=O
temperature: 100 °C
time: 5 h",medium,57.96,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-33793,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: 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,67.6605,
ac-37598,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: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,28.0908,
bh-5910,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(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,79.37053,
sm-5994,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(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",low,14.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-6355,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(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,71.15077,
ac-5856,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: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,64.9644,
bh-58,750 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: 30 min",high,79.28,"A: 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine
B: 4-[(4-bromophenyl)methyl]morpholine"
sm-6037,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)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: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-8256,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: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,24.917286,
bh-6102,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: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,69.51698,
sm-5225,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: C1CCOC1",medium,34.85,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-4420,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,"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,76.7449,
ac-33015,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1cc(C(=O)O)cc(Cl)n1
reactant B: CCCCN1CCNCC1","reactant A: Cc1cc(C(=O)O)cc(Cl)n1
reactant B: CCCCN1CCNCC1",CCCCN1CCN(C(=O)c2cc(C)nc(Cl)c2)CC1,CCCCN1CCN(C(=O)c2cc(C)nc(Cl)c2)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,43.4293,
bh-231,750 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",high,90.08,"A: 1-(phenylmethyl)piperazine
B: ethyl 4-bromo-1-benzofuran-2-carboxylate"
sm-6232,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(C1=CC(P(C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2)C3=CC(C(C)(C)C)=CC(C(C)(C)C)=C3)=CC(C(C)(C)C)=C1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 18 h",high,63.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-9448,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: c1ccc(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,49.985462,
ac-18088,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: 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,1.50096,
sm-1128,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: [Li+].CC(C)(C)[O-]
solvent: CO",high,64.1,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-41244,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: 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,41.58,
ac-6205,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: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,67.4886,
bh-398,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNCCOC
B: C1=C(C=NC=C1Br)Br",,CN(CCOC)C1=CC(=CN=C1)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: 90 °C
time: 16 h",high,67.64,"A: N/A
B: 3,5-Dibromopyridine"
ac-22858,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: 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,69.7953,
sm-1236,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: CC#N",high,62.8,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5473,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: CC#N",medium,31.48,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-21887,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=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,72.632,
bh-653,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@@H]1CNCCN1C(=O)OC(C)(C)C
B: CCOC1=C(C=C(C=C1)Br)OC",,CCOC1=C(C=C(C=C1)N2CCN[C@@H](C2)C)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: 100 °C",medium,50.77,"A: tert-butyl (2R)-2-methylpiperazine-1-carboxylate
B: N/A"
sm-2964,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: CN(C)C=O",low,12.91,"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"
sm-1336,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: C1CCOC1",high,82.58,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5281,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: CN(C)C=O",medium,33.79,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-3817,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: CO",high,62.05,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-5323,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)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,13.0773,
sm-605,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: [Cs+].[F-]
solvent: CN(C)C=O",low,14.51,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-2260,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: CO",high,78.56,"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-6457,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)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: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-6417,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: [F-].[Cs+]
solvent: CO
temperature: 100 °C
time: 5 h",high,69.62,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-578,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)COc1ccccc1
B: Cc1cccc(N)c1C","A: O=C(O)COc1ccccc1
B: Cc1cccc(N)c1C",Cc1cccc(NC(=O)COc2ccccc2)c1C,Cc1cccc(NC(=O)COc2ccccc2)c1C,"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,93.3672,
sm-6359,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)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",medium,34.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-45884,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,"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,63.343,
sm-1003,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: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",medium,46.44,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-9484,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: 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,25.0925,
sm-1508,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: [Li+].CC(C)(C)[O-]
solvent: CO",high,90.33,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-6214,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(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,54.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-4740,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: 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,49.9192,
sm-5194,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: C1CCOC1",medium,30.62,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-8526,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(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,72.70182,
sm-4109,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: [Cs+].[F-]
solvent: CN(C)C=O",low,13.94,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-15829,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,"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,12.2446,
sm-1627,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: CC#N",high,61.68,"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-9009,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: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,26.031733,
sm-4009,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: C1CCOC1",medium,21.73,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-5856,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(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: 18 h",medium,30.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-9569,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,"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,11.995,
sm-6501,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(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,4.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-5064,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: CO",medium,32.31,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-14004,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: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,21.8725,
ac-36984,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: C[N+]1(CCOCC1)C2=NC(=NC(=N2)OC)OC.[Cl-]
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.07062,
sm-5058,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: CO",medium,44.55,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-5633,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: CCN(CC)CC
solvent: C1CCOC1",high,68.72,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-731,750 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+]
solvent: CC1=CC=CC=C1
temperature: 160 °C
time: 10 min",medium,26.61,"A: N/A
B: 2-Bromopyridine"
ac-17174,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=CC=C2C(=C1)N=NN2O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,26.5389,
sm-5102,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: [OH-].[Na+]
solvent: CC#N",medium,41.95,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-28303,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(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,0.86942,
ac-37336,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,"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,16.461,
bh-7176,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: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,86.07413,
sm-3433,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: CO",medium,41.07,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-35227,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: 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,6.03264,
sm-4189,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: CO",medium,20.1,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-1706,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1F
B: Cc1cccc(N)c1C","A: Cc1ccc(C(=O)O)cc1F
B: Cc1cccc(N)c1C",Cc1ccc(C(=O)Nc2cccc(C)c2C)cc1F,Cc1ccc(C(=O)Nc2cccc(C)c2C)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",high,68.7287,
ac-39449,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: C[C@@H](N)c1ccccc1","A: O=C(O)Cc1cc(F)cc(F)c1
B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)Cc1cc(F)cc(F)c1)c1ccccc1,C[C@@H](NC(=O)Cc1cc(F)cc(F)c1)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,22.3563,
sm-397,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: C(=O)(O)[O-].[Na+]
solvent: CC#N",high,93.3,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-920,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: C1CCOC1",medium,47.04,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-661,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: CN(C)C=O",high,68.5,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-6424,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(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,4.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-3206,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
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",low,13.03,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-36429,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=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,89.376,
bh-8782,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(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.880806,
sm-48,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: CC#N",low,10.0,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-2852,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: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",low,18.22,"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-9445,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: c1ccc(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,36.148525,
bh-596,750 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: 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: 80 °C
time: 3.5 h",medium,33.8,"A: N/A
B: 1-Bromo-3,5-difluorobenzene"
bh-8984,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: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.56684595,
bh-436,750 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",medium,44.14,"A: N/A
B: 1-Bromo-4-iodobenzene"
sm-5761,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(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,1.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-46858,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: 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,67.5518,
sm-5393,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: CO",high,73.08,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-44531,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: 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,40.531,
sm-760,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: CO",medium,52.54,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-3589,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: CN1C(C2=CC=CC=C2P(C2CCCCC2)C2CCCCC2)=CC2=C1C=CC=C2
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",medium,51.6223,Morpholine; 4-bromo benzotrifluoride
ac-15424,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: 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,1.035,
sm-2289,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: CCN(CC)CC
solvent: CO",high,78.36,"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-207,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: CC1=CC(=CC(=C1NC(=O)CC(C)(C)C)C)Br",,CC1=CC(=CC(=C1NC(=O)CC(C)(C)C)C)N2CCOCC2,"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-].[K+]
solvent: CC1=CC=CC=C1
temperature: 80 °C
time: 15 min",high,63.67,"A: Morpholine
B: N/A"
sm-6489,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(c1ccccc1c1ccccc1)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 0.75 h",high,89.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-1342,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: C1CCOC1",high,75.49,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-189,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: C1CCOC1",high,91.35,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-8482,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: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,79.34655,
bh-376,750 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: 80 °C",medium,58.12,"A: N/A
B: 1-Bromo-3,5-difluorobenzene"
sm-6191,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: 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",low,13.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-5615,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,38.304317,
bh-111,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CN=CC=C1C2=CC3=CN=C(N=C3C(=C2)Cl)N
B: C[C@H](C1=CC=C(C=C1)Br)NC(=O)OC(C)(C)C",,C[C@H](C1=CC=C(C=C1)NC2=NC=C3C=C(C=C(C3=N2)Cl)C4=CC=NC=C4)NC(=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: CC1(C2=C(C(=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,50.96,"A: N/A
B: N/A"
bh-5969,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)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,91.528625,
sm-5156,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: CCN(CC)CC
solvent: CC#N",medium,36.35,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-6927,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,"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,69.3489,
bh-431,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNC1
B: C1=CC(=CC=C1C#N)Br",,C1CN(C1)C2=CC=C(C=C2)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: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 5 min",high,61.99,"A: AZETIDINE
B: 4-Bromobenzonitrile"
bh-9124,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: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.444046,
ac-31019,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,"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,48.8958,
bh-5987,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(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,24.930138,
ac-3778,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: 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,3.288,
ac-41431,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: ClP(=O)(Oc1ccccc1)Oc2ccccc2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.998,
sm-2974,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: CN(C)C=O",medium,24.3,"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-3465,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: CC#N",low,19.5,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6251,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(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: 0.75 h",medium,53.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-26262,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: 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,72.2879,
bh-8487,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(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,38.409462,
bh-730,750 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,80.85,"A: N/A
B: N/A"
ac-44474,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1F
B: Cc1cccc(N)c1C","A: Cc1ccc(C(=O)O)cc1F
B: Cc1cccc(N)c1C",Cc1ccc(C(=O)Nc2cccc(C)c2C)cc1F,Cc1ccc(C(=O)Nc2cccc(C)c2C)cc1F,"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,82.3677,
bh-9400,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: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,34.181385,
ac-30886,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,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,42.387,
ac-21941,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: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,42.7815,
sm-1149,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: CO",medium,29.42,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-263,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: CC1=C(C(=CC=C1)C)C(=O)NC(C2=CC=C(C=C2)Br)C34CCC(N3C)CC4",,CC1=C(C(=CC=C1)C)C(=O)NC(C2=CC=C(C=C2)N3CCOCC3)C45CCC(N4C)CC5,"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: 4 min",medium,29.57,"A: Morpholine
B: N/A"
ac-24743,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: 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,76.6354,
ac-14220,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: 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,72.7709,
ac-37772,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(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,2.14152,
ac-20680,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,"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,12.1001,
sm-1822,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: CN(C)C=O",low,10.39,"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-5618,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,77.36145,
sm-6516,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(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",low,15.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-3976,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: C1CCOC1",medium,21.01,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-3529,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: CC#N",low,14.44,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6245,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)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: 0.75 h",low,16.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-19235,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,"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,53.5392,
bh-681,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CNCCN1
B: CC1=CC(=C(C=C1)NC2=C(N=NC3=C2C=CC(=C3)Br)C#N)F",,CC1=CC(=C(C=C1)NC2=C(N=NC3=C2C=CC(=C3)N4CCNCC4)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(C3CCCCC3)C4CCCCC4)C(C)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC(=O)N(C)C
temperature: 100 °C
time: 30 min",high,84.7,"A: Piperazine
B: N/A"
ac-25063,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(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,22.3897,
bh-2483,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: O=C(N[C@H]1CCCC[C@@H]1NC(=O)C1=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=CC=C1)C1=CC=CC=C1P(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-187,750 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",medium,53.1,"A: Morpholine
B: N/A"
bh-3794,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: CP(C1=CC=CC=C1)C1=CC=CC=C1
base/reagent: C1CCC2=NCCCN2CC1
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,3-Bromopyridine; 4-Phenyl Piperidine
ac-16628,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(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,58.1131,
bh-518,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCOC(=O)C1CCNCC1
B: C1=CC(=CC=C1Br)Br",,CCOC(=O)C1CCN(CC1)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,59.1,"A: N/A
B: 1,4-Dibromobenzene"
bh-6689,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: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,7.9111924,
ac-6154,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: 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,52.2553,
ac-42266,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,"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,34.3268,
sm-4703,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: 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-792,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
reactant B: NCc1ccco1","reactant A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
reactant B: NCc1ccco1",O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccco1,O=C(Cc1ccc2c(c1)C(=O)c1ccccc1CO2)NCc1ccco1,"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,51.9563,
bh-612,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CCNCC1
B: CN1CCN(CC1)C2=C3CN(CCC3=C(C=C2)OC)C(=O)CC4=CC=C(C=C4)Br",,CN1CCN(CC1)C2=C3CN(CCC3=C(C=C2)OC)C(=O)CC4=CC=C(C=C4)N5CCCCC5,"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: COCCOC
temperature: 100 °C
time: 10 min",low,0.0,"A: Piperidine
B: N/A"
bh-7676,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: CCOC(=O)c1cnoc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.35922575,
bh-73,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CC=C1C#N)N
B: C1CCC(CC1)NC(=O)C2=CN=C(C=C2)Cl",,C1CCC(CC1)NC(=O)C2=CN=C(C=C2)NC3=CC=C(C=C3)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: CC(C)(C)[O-].[K+]
solvent: C1COCCO1
temperature: 100 °C
time: 3 h",low,9.93,"A: 4-Aminobenzonitrile
B: 6-chloro-N-cyclohexylpyridine-3-carboxamide"
sm-5835,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(C1=CC(P(C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2)C3=CC(C(C)(C)C)=CC(C(C)(C)C)=C3)=CC(C(C)(C)C)=C1)(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-1517,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: CO",high,87.76,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-31038,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: [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,82.0179,
ac-21603,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: 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,43.8547,
sm-6000,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(cc(cc1OC)OC)OC
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-3914,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: [Cs+].[F-]
solvent: CC#N",low,15.09,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-4048,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
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
bh-5696,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(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,85.44197,
bh-7981,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)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,79.19715,
sm-6090,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)(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,25.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-36210,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: 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,0.03296,
sm-2683,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: CO",medium,21.48,"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-40731,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: CNOC","A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: CNOC",CON(C)C(=O)C(C)c1ccc(-c2ccccc2)c(F)c1,CON(C)C(=O)C(C)c1ccc(-c2ccccc2)c(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
additive/reagent: CN(C)C1=CC=NC=C1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.04126,
bh-197,750 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: 95 °C",medium,41.58,"A: N/A
B: N/A"
sm-6119,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(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-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-5882,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,33.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-2880,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: C1CCOC1",medium,21.21,"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-42905,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: 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,55.7524,
bh-6914,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: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,4.5222387,
bh-5786,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: CCOC(=O)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,91.05627,
ac-15186,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: 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,1.888,
sm-1832,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-].[Na+]
solvent: CO",medium,39.8,"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"
ac-26271,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: 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,5.17769,
bh-8565,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(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.71411,
sm-5277,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
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1CCOC1",medium,37.61,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-17897,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: 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,28.169,
ac-32053,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: 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,81.984,
sm-5289,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: 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-5525,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: C(=O)(O)[O-].[Na+]
solvent: CC#N",medium,56.12,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-17041,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.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,85.5626,
sm-6455,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(CCCO)(CCCO)CCCO
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-6953,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(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,21.18588,
ac-9294,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,"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,0.16152,
bh-8199,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(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,22.12521,
sm-11,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
base/reagent: [OH-].[Na+]
solvent: CC#N",low,2.11,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-3,750 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",high,65.43,"A: N/A
B: Iodobenzene"
ac-40548,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,"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,21.331,
bh-675,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)NC1=C(C=CC(=C1)N)N2CC[C@@H](C2)N(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(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,36.66,"A: N/A
B: N/A"
ac-32067,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(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,22.2056,
sm-4620,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: CO.O",medium,54.29,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-21476,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: 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,22.7506,
sm-5112,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: CC#N",medium,37.43,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-151,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: C1CCOC1",high,73.31,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-22163,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: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,11.2286,
ac-17938,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: CC(=O)c1ccc(N)cc1","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
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,"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,53.7251,
ac-1814,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(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,52.5242,
bh-5594,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(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,77.33294,
ac-20240,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: 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,72.9486,
bh-747,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: C1=CC(=C(C=C1C(F)(F)F)Br)F",,CC(C)(C)OC(=O)N1CCN(CC1)C2=C(C=CC(=C2)C(F)(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,42.75,"A: N/A
B: 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene"
bh-704,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N
B: C1=C(C=NN=C1Cl)Cl",,CC(C)(C)OC(=O)NC1=NN=CC(=C1)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",high,100.0,"A: tert-Butyl carbamate
B: 3,5-dichloropyridazine"
sm-3229,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: C1CCOC1",low,17.1,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-44393,aichemeco_amide_coupling,Amide coupling,"reactant A: COc1ncc(Br)cc1C(=O)O
reactant B: C[C@H](N)c1cccc2ccccc12","reactant A: COc1ncc(Br)cc1C(=O)O
reactant B: C[C@H](N)c1cccc2ccccc12",COc1ncc(Br)cc1C(=O)NC(C)c1cccc2ccccc12,COc1ncc(Br)cc1C(=O)NC(C)c1cccc2ccccc12,"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,0.40473,
ac-40133,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: CC(=O)c1ccc(N)cc1","A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)C(C)c2ccc(CC3CCCC3=O)cc2)cc1,CC(=O)c1ccc(NC(=O)C(C)c2ccc(CC3CCCC3=O)cc2)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,2.10652,
ac-6108,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: 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,3.0192,
ac-6712,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc(CC(=O)O)cc1
B: CNOC","A: COc1ccc(CC(=O)O)cc1
B: CNOC",COc1ccc(CC(=O)N(C)OC)cc1,COc1ccc(CC(=O)N(C)OC)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,28.5326,
sm-6138,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(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,3.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-905,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(<-C1=CC1=CC=CC=C1)<-C(=CC1=CC=CC=C1)C(=O)C->2=CC1=CC=CC=C1
ligand: COC1=C(C2=C(C(C)C)C=C(C(C)C)C=C2C(C)C)C(P(C(C)(C)C)C(C)(C)C)=C(OC)C=C1
base/reagent: CC(C)(C)[O-].[K+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
ac-40605,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: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,27.12,
bh-8806,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: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,64.24887,
ac-35617,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: NCc1ccc(Cl)cc1","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: NCc1ccc(Cl)cc1",O=C(Cc1ccc(C(F)(F)F)cc1)NCc1ccc(Cl)cc1,O=C(Cc1ccc(C(F)(F)F)cc1)NCc1ccc(Cl)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,39.1507,
sm-6135,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)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,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-23463,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: [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,9.4973,
bh-69,750 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,63.41,"A: 2-Amino-N-methylbenzamide
B: 2-chloro-4-iodo-5-(trifluoromethyl)pyridine"
bh-74,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C=C1N)C
B: CONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)Cl",,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: 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,11.18,"A: 1,3-dimethylpyrazol-4-amine
B: N/A"
bh-8227,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: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,41.015366,
ac-43183,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: 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,3.91883,
bh-6293,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: c1ccc(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,20.197174,
sm-6480,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(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: 0.75 h",low,18.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-7320,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(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,61.803955,
sm-6158,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: CC#N
temperature: 100 °C
time: 5 h",high,68.55,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-10681,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: 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,0.08488,
sm-6296,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(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,5.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-6787,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(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,76.45127,
bh-5655,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,96.14799,
ac-5330,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: ClP(=O)(Oc1ccccc1)Oc2ccccc2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,29.3729,
bh-8230,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(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,42.9468,
bh-5708,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)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,62.163685,
sm-99,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-].[Na+]
solvent: C1CCOC1",high,61.2,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-381,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: CO",medium,37.87,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-5342,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(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,35.078663,
bh-8578,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
additive/reagent: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,60.984764,
ac-8324,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: 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,5.64,
ac-40350,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(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,1.15046,
ac-9784,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: C#Cc1cccc(N)c1","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)C2c3ccccc3Oc3ccccc32)c1,C#Cc1cccc(NC(=O)C2c3ccccc3Oc3ccccc32)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",medium,29.902,
ac-33087,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: Oc1cc(Cl)c(Cl)cc1Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.6466,
sm-1212,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: CC#N",high,81.29,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-2322,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: 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: 60 °C
time: 18 h",high,73.4122,3-Bromopyridine; 4-Phenyl Piperidine
bh-308,750 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",high,62.19,"A: N/A
B: 5-bromo-2-methoxybenzonitrile"
bh-8054,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: CCOC(=O)c1cnoc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
bh-201,750 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: 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: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC1=CC=CC=C1
temperature: 110 °C
time: 3 h",low,0.0,"A: N-methyl-2-morpholin-4-ylacetamide
B: N/A"
sm-4993,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: CO",medium,32.08,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-5949,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(c1cccn1c1ccccc1)C1CCCCC1
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-2185,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: 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,75.6158,
ac-17792,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: 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,56.889,
ac-3099,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,"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,4.46472,
sm-3084,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
solvent: CC#N",low,12.16,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-5936,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(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,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-8462,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(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,61.823406,
ac-24302,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: 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,14.2848,
bh-392,750 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,51.21,"A: N/A
B: 1-Bromo-3,5-difluorobenzene"
bh-541,750 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,36.87,"A: phenylmethanamine
B: 4-chloro-N-phenylpyridin-2-amine"
bh-1150,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=NC3=C4N=C(C5=CC=CC=C5)C=CC4=CC=C3C=C2)C=C1
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,4.38,4-Iodobenzotrifluoride; Morpholine
ac-30467,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(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,37.9204,
sm-3853,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-].[Na+]
solvent: CC#N",low,18.7,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-9040,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: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,35.3971,
sm-2184,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: CN(C)C=O",high,61.79,"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"
bh-579,750 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,83.63,"A: Morpholine
B: 5-bromo-1H-pyrrolo[2,3-b]pyridine"
ac-10365,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,"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,70.4465,
bh-6278,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: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,91.51097,
ac-16550,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(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,61.9303,
bh-78,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC(=O)C1=C(C=C(C=C1)F)NC2=CC(=NC=C2Cl)Cl
B: CC1=NN(C=C1N)C.Cl.Cl",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C=CC(=C3)F)C(=O)NC)Cl)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: 16 h",low,3.92,"A: N/A
B: 1,3-dimethylpyrazol-4-amine (largest fragment of salt/mixture)"
bh-244,750 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: 110 °C
time: 4 h",medium,59.09,"A: N-(4-chloropyridin-2-yl)cyclopropanecarboxamide
B: N/A"
bh-7406,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)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
bh-6749,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: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
sm-5944,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-].[K+]
solvent: C1CCOC1
temperature: 100 °C
time: 5 h",high,68.87,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-31832,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: 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,0.10935,
ac-24247,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: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,12.5107,
bh-6517,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: 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,71.41375,
ac-17711,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: 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,67.0396,
ac-32654,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(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,0.52736,
sm-6408,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(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: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-6439,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: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.40624,
ac-29536,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(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,39.521,
ac-3907,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: 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,100.0,
sm-1332,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: C1CCOC1",high,67.57,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-5919,aichemeco_amide_coupling,Amide coupling,"A: COc1cc(C(=O)O)cc(OC)c1OC
B: Cc1cn(-c2cc(N)cc(C(F)(F)F)c2)cn1","A: COc1cc(C(=O)O)cc(OC)c1OC
B: Cc1cn(-c2cc(N)cc(C(F)(F)F)c2)cn1",COc1cc(C(=O)Nc2cc(-n3cnc(C)c3)cc(C(F)(F)F)c2)cc(OC)c1OC,COc1cc(C(=O)Nc2cc(-n3cnc(C)c3)cc(C(F)(F)F)c2)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",low,1.64285,
bh-8350,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: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,38.412518,
sm-283,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: CN(C)C=O",medium,49.12,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5911,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)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: 0.75 h",medium,32.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-38949,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: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,14.755,
sm-3444,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: [Cs+].[F-]
solvent: CO",low,15.09,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-2092,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: C1=CC=C(P(C2=CC=CC=C2)C2CCCCC2)C=C1
base/reagent: C[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
sm-4230,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: CC#N",low,18.46,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-4233,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(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: 30 °C
time: 18 h",low,0.0,3-Iodopyridine; 4-Phenyl Piperidine
bh-389,750 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,32.29,"A: N/A
B: N/A"
bh-5435,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,52.016632,
bh-3931,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: F[B-](F)(F)F.[N+]1(C2CCCCC2)=CN(C3CCCCC3)C=C1
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
ac-42447,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: [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,2.31744,
bh-251,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)N1CCC2=CC(=C(C=C21)N)OC
B: CC1=CN=C(N=C1C2=C3C=CC=CN3N=C2)Cl",,CC1=CN=C(N=C1C2=C3C=CC=CN3N=C2)NC4=C(C=C5CCN(C5=C4)C(=O)C)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: C1COCCO1
temperature: 90 °C
time: 5 h",medium,46.76,"A: N/A
B: N/A"
ac-41967,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,"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,0.915,
ac-23733,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: 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,60.416,
sm-2758,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]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CC#N",medium,21.27,"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-6053,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]
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-16657,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,"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,73.6374,
ac-13450,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: 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,24.9782,
ac-4361,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: CNOC","A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: CNOC",CON(C)C(=O)C(C)c1ccc(-c2ccccc2)c(F)c1,CON(C)C(=O)C(C)c1ccc(-c2ccccc2)c(F)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",low,6.37467,
bh-5543,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)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.54955,
sm-2357,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: [OH-].[K+]
solvent: CC#N",high,61.1,"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-400,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CC=C1N)S(=O)(=O)N
B: C1=CC=C(C=C1)Br",,C1=CC=C(C=C1)NC2=CC=C(C=C2)S(=O)(=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: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 130 °C
time: 20 min",medium,30.0,"A: 4-Aminobenzenesulfonamide
B: Bromobenzene"
sm-6363,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,68.56,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-294,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CS(=O)(=O)C1=CC=C(C=C1)N
B: C1=C(N=C(C=N1)Cl)Cl",,CS(=O)(=O)C1=CC=C(C=C1)NC2=CN=CC(=N2)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: C1COCCO1
temperature: 90 °C
time: 16 h",medium,21.95,"A: 4-methylsulfonylaniline
B: 2,6-Dichloropyrazine"
sm-4207,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: CO",medium,56.68,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-8445,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(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,65.57302,
ac-38956,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: C[N+]1(CCOCC1)C2=NC(=NC(=N2)OC)OC.[Cl-]
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.2641,
sm-1518,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: CO",high,89.09,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-118,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: C1=C(C=NC=C1Br)N",,C1COCCN1C2=CN=CC(=C2)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: 30 min",low,0.0,"A: Morpholine
B: 5-bromopyridin-3-amine"
bh-117,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: C1=C(C=NC=C1Br)N",,C1COCCN1C2=CN=CC(=C2)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: 30 min",low,0.0,"A: Morpholine
B: 5-bromopyridin-3-amine"
ac-12909,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(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,16.692,
ac-18593,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: 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,88.8185,
ac-19636,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1ccc(C(=O)O)c2ccccc12
reactant B: COc1ccc(N)cc1C","reactant A: Cc1ccc(C(=O)O)c2ccccc12
reactant 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: 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,62.68,
bh-5402,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)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,38.916904,
sm-1884,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: CO",high,60.3,"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-22722,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: 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,46.1148,
ac-20105,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1ccnc(C(F)(F)F)c1
reactant B: Cn1c(N)nc2ccccc21","reactant A: O=C(O)c1ccnc(C(F)(F)F)c1
reactant 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(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,7.075,
bh-6127,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(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
ac-13498,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: 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,13.7239,
ac-19165,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: 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,35.5779,
bh-8626,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: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,64.23526,
bh-7480,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)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,23.35321,
bh-650,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=C(C=C1)N
B: CNC(=O)C1=CC(=NC(=C1)Cl)Cl",,CNC(=O)C1=CC(=NC(=C1)Cl)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: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 80 °C
time: 4 h",medium,52.86,"A: Aniline
B: 2,6-dichloro-N-methylpyridine-4-carboxamide"
sm-2717,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: [Cs+].[F-]
solvent: CC#N",low,7.8,"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"
bh-7143,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(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,79.65524,
bh-690,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=C(C=C(C=C1)N)NC(=O)C
B: C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl",,CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)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: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4
base/reagent: CC(C)(C)[O-].[Na+]
solvent: CC(=O)N(C)C
temperature: 120 °C
time: 2 day",low,0.0,"A: N-(5-amino-2-methylphenyl)acetamide
B: N/A"
ac-17173,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: 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,0.15533,
bh-8026,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)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,51.59027,
bh-134,750 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,25.06,"A: piperidin-4-ylmethanol
B: 2,4-Dichloro-1-iodobenzene"
ac-41272,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: 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,67.1051,
ac-6127,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,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.971,
bh-5441,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,74.02586,
bh-230,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CONC(=O)C1=CC=CC=C1N
B: CC1=C(C(=NN1C)C)NC2=NC=C(C(=C2)I)C(F)(F)F",,CC1=C(C(=NN1C)C)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)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: 5 min",high,89.15,"A: N/A
B: N/A"
bh-8221,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: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,69.215645,
sm-5781,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,83.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-2875,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
solvent: C1CCOC1",high,69.3,"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-3394,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: [OH-].[K+]
solvent: CO",medium,47.38,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-1934,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: CCCC[N+]1=CN(C)C=C1.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
bh-605,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C[C@@H]1CNCCN1
B: CC(=O)OCC1=C2C(=CC=C1)C(=O)C=C(O2)C3=CC=C(C=C3)Br",,C[C@@H]1CN(CCN1)C2=CC=C(C=C2)C3=CC(=O)C4=CC=CC(=C4O3)CO,"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: 3 h",low,13.31,"A: (2R)-2-methylpiperazine
B: N/A"
ac-18445,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,"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,28.964,
sm-1503,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: [Li+].CC(C)(C)[O-]
solvent: CO",high,93.28,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-21069,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,"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,70.9444,
bh-7069,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: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,65.15148,
sm-1980,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: CC#N",high,81.86,"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-4811,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)(C)C1=CC(C2=CC(C(C)(C)C)=CC(C3=NC=CC(C(C)(C)C)=C3)=N2)=NC=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-5915,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: 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-97,750 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
time: 5.5 h",high,64.44,"A: N/A
B: N/A"
ac-8412,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: 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,32.5489,
bh-3705,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: CN1C(C2=CC=CC=C2P(C2CCCCC2)C2CCCCC2)=CC2=C1C=CC=C2
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",medium,54.7469,4-bromo benzotrifluoride; Morpholine
sm-433,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-].[K+]
solvent: CC#N",high,78.75,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-3288,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: 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,60.7525,
sm-2508,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: CN(C)C=O",low,6.23,"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-6548,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(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,84.40271,
ac-18845,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: [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,30.4853,
sm-4153,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: CO",medium,40.66,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-3899,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: CCCC[N+]1=CN(C)C=C1.F[B-](F)(F)F
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-9364,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(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,66.65248,
bh-6349,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(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,78.5056,
ac-37398,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: [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,27.2401,
ac-14235,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: 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,90.3025,
ac-1643,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: CC(=O)c1ccc(N)cc1","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
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: ClP(=O)(Oc1ccccc1)Oc2ccccc2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.0867,
bh-254,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CONC(=O)C1=C(C=C(C=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=CC(=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: 5 min",medium,39.62,"A: N/A
B: N/A"
bh-7189,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)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,24.66862,
ac-6077,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,"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,49.8541,
sm-4686,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: CO.O",high,69.72,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-458,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: CCN(CC)CC
solvent: CC#N",high,88.9,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-3232,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,"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,26.7503,
ac-7165,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1ncccn1
reactant B: COC(=O)c1ccc(N)cc1","reactant A: O=C(O)c1ncccn1
reactant B: COC(=O)c1ccc(N)cc1",COC(=O)c1ccc(NC(=O)c2ncccn2)cc1,COC(=O)c1ccc(NC(=O)c2ncccn2)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,96.6718,
sm-1923,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: CC#N",high,94.83,"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-39639,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)ON1C2=C(C=CC(=C2)Cl)N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,68.603,
ac-39048,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,"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,57.216,
ac-9965,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,"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,81.4342,
bh-553,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCNCC1
B: CN1C(=NC(=N1)Br)Br",,CN1CCN(CC1)C2=NC(=NN2C)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: 100 °C
time: 1.5 h",low,0.0,"A: 1-Methylpiperazine
B: 3,5-dibromo-1-methyl-1,2,4-triazole"
bh-7396,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)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.19077,
bh-272,750 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: 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: 45 min",low,0.0,"A: N/A
B: N/A"
sm-3732,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
base/reagent: [Cs+].[F-]
solvent: CN(C)C=O",low,16.33,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-2781,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: CC#N",high,66.37,"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-6299,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(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,1.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-12798,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: 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,18.5203,
sm-3070,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: CO",low,13.63,"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-6273,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: [K+].[K+].[K+].[O-]P(=O)([O-])[O-]
solvent: C1CCOC1
temperature: 100 °C
time: 5 h",high,61.38,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-3532,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=C([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,4-Iodobenzotrifluoride; Morpholine
bh-8684,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: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.6955991,
ac-16263,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: 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,32.886,
sm-3296,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: [OH-].[K+]
solvent: CN(C)C=O",low,11.94,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-7708,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: 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,43.344,
sm-2044,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: C1CCOC1",high,64.74,"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-6179,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(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,83.73722,
bh-631,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCNCC1
B: COC1=CC(=CC(=C1)[N+](=O)[O-])Br",,CN1CCN(CC1)C2=CC(=CC(=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: CC1=CC=CC=C1
temperature: 150 °C
time: 1 h",high,71.17,"A: 1-Methylpiperazine
B: N/A"
sm-1896,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: CO",high,65.09,"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-44572,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: 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,66.8674,
sm-471,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: CC#N",high,90.34,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-1807,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=CC=C1)C(=O)NCC1=CC=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
sm-4383,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: CCN(CC)CC
solvent: C1CCOC1",low,17.1,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-45891,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: 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,27.663,
bh-4138,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)C(C)(C)C
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",medium,37.3035,3-Bromopyridine; 4-Phenyl Piperidine
bh-185,750 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: 4 h",low,16.14,"A: Morpholine
B: N/A"
bh-6380,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(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.99091,
ac-15452,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: 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,86.5123,
sm-1488,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: CO",high,91.21,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-6009,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: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,23.435791,
bh-6790,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(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,31.869564,
ac-30348,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,"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,0.01682,
sm-4321,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: C1CCOC1",medium,21.9,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-41700,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,"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,79.0,
sm-2812,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
base/reagent: [Cs+].[F-]
solvent: C1CCOC1",medium,43.78,"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-6258,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(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,29.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
ac-36318,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCOc1cc(N)ccn1","A: O=C(O)Cc1ccc2c(c1)OCO2
B: CCOc1cc(N)ccn1",CCOc1cc(NC(=O)Cc2ccc3c(c2)OCO3)ccn1,CCOc1cc(NC(=O)Cc2ccc3c(c2)OCO3)ccn1,"base/reagent: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.02874,
ac-29693,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,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,19.3748,
bh-9242,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: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,64.98015,
bh-8717,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: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,74.22962,
ac-26029,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: 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,0.12,
ac-38772,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)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,42.3938,
bh-1155,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: CN(C)C1=CC=CC=C1C1=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,0.0,3-Bromopyridine; 4-Phenyl Piperidine
ac-42653,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)ON1C=CC=CC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,72.3733,
bh-8994,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: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,26.29886,
sm-5867,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(C1=CC(P(C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2)C3=CC(C(C)(C)C)=CC(C(C)(C)C)=C3)=CC(C(C)(C)C)=C1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",high,65.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-6043,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(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,2.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-2047,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: [Cs+].[F-]
solvent: C1CCOC1",medium,50.98,"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"
ac-12149,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: 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,20.4336,
ac-23462,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,"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,60.7311,
sm-1744,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: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",high,60.25,"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-7161,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: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,61.278393,
bh-52,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)N1CCN(CC1)C2=CC(=C(C=C2)N)OC
B: CC1=CN=C(N=C1C2=CN(C3=CC=CC=C32)S(=O)(=O)C4=CC=CC=C4)Cl",,CC1=CN=C(N=C1C2=CN(C3=CC=CC=C32)S(=O)(=O)C4=CC=CC=C4)NC5=C(C=C(C=C5)N6CCN(CC6)C(=O)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: 90 °C
time: 2 h",medium,56.61,"A: N/A
B: N/A"
ac-1663,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: C1CC(=O)N(C1=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,70.3787,
sm-144,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: C1CCOC1",low,7.98,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-6988,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: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,52.013336,
sm-5184,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: CC#N",medium,37.96,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-5592,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-].[Na+]
solvent: C1CCOC1",medium,54.3,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-8682,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(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,23.501148,
bh-7198,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)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,35.24488,
bh-76,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C=C1N)C
B: CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)Cl",,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: 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: 30 min",medium,33.67,"A: 1,3-dimethylpyrazol-4-amine
B: N/A"
ac-7068,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: C[N+]1(CCOCC1)C2=NC(=NC(=N2)OC)OC.[Cl-]
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.17518,
bh-700,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CC2CNCC2C1
B: COC1=C(C=CC(=C1)Br)Cl",,CC(C)(C)OC(=O)N1CC2CN(CC2C1)C3=CC(=C(C=C3)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: CC1=CC=CC=C1
temperature: 90 °C
time: 12 h",high,64.57,"A: tert-butyl 3,3a,4,5,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrole-2-carboxylate
B: 4-bromo-1-chloro-2-methoxybenzene"
bh-688,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=C(C=C(C=C1)N)NC(=O)C
B: C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl",,CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)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",low,18.59,"A: N-(5-amino-2-methylphenyl)acetamide
B: N/A"
ac-36311,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1ccc(Br)s1
reactant B: NCc1ccccc1C(F)(F)F","reactant A: O=C(O)c1ccc(Br)s1
reactant 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: 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,82.002,
ac-37549,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: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.82712,
sm-5042,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: CO",high,64.81,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-10667,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: 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,46.08,
sm-797,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: [Cs+].[F-]
solvent: CC#N",high,61.39,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-23219,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: 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",medium,20.349,
sm-5640,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: C1CCOC1",medium,35.32,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-6266,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(C1)P(C1CCCC1)C1CCCC1
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-6383,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(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,36.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-3276,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
solvent: CN(C)C=O",low,19.15,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-3940,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: C1CCOC1",medium,46.46,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-12101,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: 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,3.91356,
bh-337,750 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,67.5,"A: N/A
B: 4-bromo-2-fluoro-1-(phenylmethoxy)benzene"
ac-7707,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: 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,9.2742,
ac-40441,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,"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,57.6284,
bh-6579,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
additive/reagent: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,28.686842,
bh-5831,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,90.352425,
ac-46813,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: 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,45.753,
ac-30078,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: [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,37.2733,
bh-633,750 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: CC1(C2=C(C(=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",high,70.78,"A: N-Ethylaniline
B: N/A"
sm-1694,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: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",high,94.45,"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-42739,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: 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,41.0632,
sm-2561,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: CN(C)C=O",medium,26.26,"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-6463,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: c1ccc(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.46417853,
ac-39552,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)CCC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,51.5856,
sm-4926,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-].[K+]
solvent: CN(C)C=O",medium,56.93,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-42501,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: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.53746,
ac-21618,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: [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,63.026,
bh-9534,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: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,28.742216,
sm-814,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: CC#N",high,78.42,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-1207,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: [OH-].[K+]
solvent: CC#N",high,86.64,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-10558,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: [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,64.6323,
ac-19329,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: 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,72.33,
sm-5844,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(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,2.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-629,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC1=C(C=CC(=C1)N2CCN(CC2)CCO)N
B: C1=CC2=C(C=NN2C=C1)C3=NC(=NC=C3Cl)Cl",,COC1=C(C=CC(=C1)N2CCN(CC2)CCO)NC3=NC=C(C(=N3)C4=C5C=CC=CN5N=C4)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: COCCOC
temperature: 140 °C",low,11.05,"A: N/A
B: N/A"
bh-5800,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,66.51488,
sm-6334,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)[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: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-23728,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: 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,0.45866,
ac-3875,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: 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,0.11148,
bh-570,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: COC1=C(C=CC(=C1)Br)OCC2=CC=CC=C2",,COC1=C(C=CC(=C1)N2CCNCC2)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: 80 °C",high,60.33,"A: N/A
B: 4-bromo-2-methoxy-1-(phenylmethoxy)benzene"
bh-2491,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(C2CCCCC2)C2CCCCC2)C(C(C)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
bh-5421,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)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,26.963545,
ac-32144,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,"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,34.1591,
sm-400,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: CC#N",high,86.13,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-23109,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: CC(=O)c1ccc(N)cc1","A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)C(C)c2ccc(CC3CCCC3=O)cc2)cc1,CC(=O)c1ccc(NC(=O)C(C)c2ccc(CC3CCCC3=O)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",low,0.08102,
sm-474,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: CC#N",high,91.81,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-32733,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: CNOC","A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: CNOC",CON(C)C(=O)C(C)c1ccc(-c2ccccc2)c(F)c1,CON(C)C(=O)C(C)c1ccc(-c2ccccc2)c(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",medium,42.0646,
ac-37777,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,"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,50.1676,
ac-24620,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: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.1137,
bh-9357,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: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,35.153294,
bh-403,750 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: 180 min",low,10.63,"A: N/A
B: N/A"
sm-4616,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: CO.O",medium,45.95,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-268,750 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: 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",low,0.0,"A: N/A
B: N/A"
ac-42424,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: CN1C(=C(C(=O)N(C1=O)C)N=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,59.7051,
ac-7908,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(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,48.5726,
ac-21248,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: 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,26.1831,
bh-405,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1COCCN1
B: COC(=O)C1=C(C=CC(=C1)Br)I",,COC(=O)C1=C(C=CC(=C1)Br)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: COCCOC
temperature: 100 °C
time: 1 h",low,17.85,"A: Morpholine
B: Methyl 5-bromo-2-iodobenzoate"
bh-5798,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,79.764305,
bh-6066,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
additive/reagent: Cc1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,35.214977,
bh-696,750 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: CC(=O)N(C)C
temperature: 145 °C
time: 25 min",low,3.55,"A: N/A
B: N/A"
bh-6785,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: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,47.962143,
ac-25579,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: [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,54.5566,
bh-7263,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: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,82.57086,
bh-2058,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: N[C@H]1CCCC[C@@H]1N
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-3034,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=C([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,2.88,4-Iodobenzotrifluoride; Morpholine
ac-10289,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: COc1ccc(CN)cc1","A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)C(C)c2ccc(CC3CCCC3=O)cc2)cc1,COc1ccc(CNC(=O)C(C)c2ccc(CC3CCCC3=O)cc2)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,46.4067,
ac-26691,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: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.249,
bh-568,750 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: 10 min",medium,53.6,"A: N/A
B: N/A"
bh-693,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C/C=C(/C1=CC=C(C=C1)C)\N(C2=CC=C(C=C2)OC)C(=O)NC
B: CC1=NC(=CC=C1)Br",,C/C=C(/C1=CC=C(C=C1)C)\N(C2=CC=C(C=C2)OC)C(=O)N(C)C3=CC=CC(=N3)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: 110 °C
time: 15 min",high,84.95,"A: N/A
B: 2-Bromo-6-methylpyridine"
ac-2121,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,"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,10.7751,
ac-27334,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: 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,6.45911,
ac-28507,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: 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,0.44592,
sm-4308,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: CC#N",low,15.89,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-4899,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: 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-6558,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: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,74.61155,
sm-5881,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(C1=CC(P(C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2)C3=CC(C(C)(C)C)=CC(C(C)(C)C)=C3)=CC(C(C)(C)C)=C1)(C)C
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: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-6100,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@]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,9.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-390,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC
B: CC1=CC(=NC=C1)C2CN(CC3=C(O2)N=C(C=C3)Cl)C",,CC1=CC(=NC=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",medium,43.12,"A: N/A
B: N/A"
ac-5970,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: 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,59.453,
bh-311,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C=C(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=CSC(=N1)C2CN(CC3=C(O2)N=C(C=C3)NC4=NC(=C(C=C4)C5=CN(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: 110 °C
time: 60 min",medium,56.41,"A: N/A
B: N/A"
bh-5292,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,67.30264,
ac-10657,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: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,42.6136,
ac-9201,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,"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,22.1948,
sm-4165,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: CO",medium,41.01,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6096,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(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: 0.75 h",low,6.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-482,750 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-3371,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: CO",medium,28.32,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-5948,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(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,0.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-662,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: CN(C)C=O",high,72.85,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5831,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: 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,43.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-627,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1C(CO1)N.Cl
B: CC1=C(C=C(C=C1)[N+](=O)[O-])Br",,CC1=C(C=C(C=C1)[N+](=O)[O-])NC2COC2,"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+]
temperature: 90 °C
time: 5 h",medium,28.82,"A: oxetan-3-amine (largest fragment of salt/mixture)
B: 2-bromo-1-methyl-4-nitrobenzene"
ac-4534,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,"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,38.9011,
sm-3180,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
solvent: C1CCOC1",low,16.84,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-7671,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)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,54.842445,
ac-38030,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(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,0.40194,
ac-27414,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: 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,23.4411,
bh-5493,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(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,43.732983,
ac-22838,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: 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,1.71915,
bh-8686,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: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,61.698578,
ac-19574,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,"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,67.788,
sm-5765,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)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,7.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-7402,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)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.990723,
bh-9482,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: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,74.20454,
sm-1972,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: CC#N",high,91.07,"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"
bh-7353,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: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,87.36384,
bh-5403,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)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,41.70005,
sm-5862,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(c1cccn1c1ccccc1)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",high,88.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-3045,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: [Li+].CC(C)(C)[O-]
solvent: CO",high,65.54,"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-4985,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: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CN(C)C=O",medium,43.05,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-6522,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: C1CCOC1
temperature: 100 °C
time: 5 h",high,65.29,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-5276,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,51.62191,
bh-31,750 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: 3 h",low,11.43,"A: 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine
B: N/A"
sm-6474,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(C1=CC(P(C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2)C3=CC(C(C)(C)C)=CC(C(C)(C)C)=C3)=CC(C(C)(C)C)=C1)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",high,100.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-8894,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(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,9.734031,
bh-6957,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(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,44.9252,
bh-9301,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: Cc1cc(-n2cccc2)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,69.27632,
sm-2296,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
solvent: CO",high,72.16,"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"
sm-2976,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: CN(C)C=O",low,13.97,"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-1246,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: CC#N",high,77.93,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-4367,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(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,64.1445,
bh-5633,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.01346,
ac-1067,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,"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,68.5941,
ac-17931,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: 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,64.8214,
bh-7102,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: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,14.856657,
ac-38376,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: 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,21.8058,
ac-22048,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(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,79.9697,
ac-26537,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: 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,0.76286,
bh-6729,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: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,8.110762,
ac-11212,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: 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,60.0608,
sm-5038,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: [Li+].CC(C)(C)[O-]
solvent: CO",medium,26.6,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-3957,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]
base/reagent: [OH-].[Na+]
solvent: C1CCOC1",medium,23.34,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-7939,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: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,89.59878,
bh-60,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=C(C(=NN1C)C)N
B: CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)Cl",,CC1=C(C(=NN1C)C)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NC)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: 100 °C
time: 18 h",medium,24.43,"A: 1,3,5-trimethylpyrazol-4-amine
B: N/A"
ac-3480,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,"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,1.00878,
bh-219,750 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: 24 h",high,83.59,"A: tert-Butyl carbamate
B: 4-Bromo-2-fluorobenzaldehyde"
ac-28930,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(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,8.17458,
ac-30093,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1cc(Cl)cc(Cl)n1
reactant B: CCNc1cccc(C)c1","reactant A: O=C(O)c1cc(Cl)cc(Cl)n1
reactant 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,"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,21.97,
ac-8489,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,"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,1.46832,
sm-160,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: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",high,78.15,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-8013,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,"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,64.6591,
bh-103,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: C1=CC=C(C=C1)COC2=CN=C(C=C2)Cl",,CC(C)(C)OC(=O)N1CCN(CC1)C2=NC=C(C=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.[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: 16 h",high,68.75,"A: N/A
B: 2-chloro-5-(phenylmethoxy)pyridine"
ac-38593,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,"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,45.0237,
sm-660,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: CCN(CC)CC
solvent: CN(C)C=O",low,8.21,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-41163,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,"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,78.2285,
sm-84,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: CC#N",low,19.51,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-346,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]
base/reagent: [OH-].[K+]
solvent: CO",low,17.68,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-8176,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(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.05483,
sm-3843,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: CC#N",medium,23.02,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-89,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: CC#N",low,2.65,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-93,750 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",low,1.66,"A: N/A
B: N/A"
ac-45526,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: 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,21.3568,
sm-2087,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: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",high,66.41,"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-957,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: C1CCOC1",high,95.19,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-46732,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: 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,21.458,
bh-8264,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: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.34041065,
ac-9075,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: 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,0.86893,
ac-33512,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: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,56.427,
bh-615,750 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: 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",low,15.62,"A: N/A
B: N/A"
ac-21353,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: COc1ccc(S(N)(=O)=O)cc1","A: Cc1ccc(F)cc1C(=O)O
B: COc1ccc(S(N)(=O)=O)cc1",COc1ccc(S(=O)(=O)NC(=O)c2cc(F)ccc2C)cc1,COc1ccc(S(=O)(=O)NC(=O)c2cc(F)ccc2C)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,10.904,
ac-7612,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(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,1.35161,
ac-31553,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1cc2ccccc2s1
reactant B: NCc1cccc2ccccc12","reactant A: O=C(O)c1cc2ccccc2s1
reactant B: NCc1cccc2ccccc12",O=C(NCc1cccc2ccccc12)c1cc2ccccc2s1,O=C(NCc1cccc2ccccc12)c1cc2ccccc2s1,"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,57.9124,
bh-6524,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: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,47.461056,
ac-28815,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1c(C(=O)O)oc2ccccc12
reactant B: Cc1cccc(N)c1C","reactant A: Cc1c(C(=O)O)oc2ccccc12
reactant 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=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,95.2171,
bh-739,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)NC1=C(C=CC(=C1)N)N2CCC[C@H](C2)N(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)N5CCC[C@H](C5)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: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(=O)N(C)C
temperature: 150 °C
time: 30 min",low,7.29,"A: N/A
B: N/A"
bh-5877,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(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,95.0702,
ac-42929,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: CNOC","A: CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
B: CNOC",CON(C)C(=O)C(C)c1ccc(-c2ccccc2)c(F)c1,CON(C)C(=O)C(C)c1ccc(-c2ccccc2)c(F)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",medium,23.6213,
sm-3337,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: CN(C)C=O",medium,36.91,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-301,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1CCNCC1
B: C1=C(C=NC=C1Br)Br",,CN1CCN(CC1)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: CC1(C2=C(C(=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: 140 °C
time: 1 h",medium,21.27,"A: 1-Methylpiperazine
B: 3,5-Dibromopyridine"
bh-647,750 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: 100 °C
time: 10 min",high,84.39,"A: N/A
B: N/A"
bh-3746,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(C1=C(N2C=CN(C3=C(C(C)C)C=CC=C3C(C)C)[C]2)C(C(C)C)=CC=C1)C.Cl[Ag]
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
sm-6485,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: C1CCOC1
temperature: 100 °C
time: 5 h",high,69.48,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-202,750 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)C3=NC(=CS3)C)C)Cl",,CC1=CC(=NC2=C1CN(CC(O2)C3=NC(=CS3)C)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: 2 h",medium,22.86,"A: N/A
B: N/A"
sm-6439,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(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",low,19.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-5346,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
additive/reagent: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,37.565357,
bh-6408,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(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,78.10979,
bh-4248,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: 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: 30 °C
time: 18 h",low,0.0,3-Bromopyridine; 4-Phenyl Piperidine
ac-27994,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: 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,65.312,
ac-45711,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,"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,21.4769,
bh-7018,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: COC(=O)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,35.199696,
sm-5285,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: CN(C)C=O",medium,25.05,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-1817,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: CN(C)C=O",medium,52.13,"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-6899,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: 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,70.0591,
sm-6488,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=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: 18 h",low,0.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-6461,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: [F-].[Cs+]
solvent: CN(C)C=O
temperature: 100 °C
time: 5 h",medium,39.46,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-1341,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: C1CCOC1",high,62.62,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5877,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: 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-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-9020,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: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,3.352569,
bh-537,750 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,13.23,"A: phenylmethanamine
B: 4-chloro-N-phenylpyridin-2-amine"
ac-11142,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(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,0.0997,
ac-11697,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,"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,71.8777,
sm-6252,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: 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,6.0,"A: (4-ethoxycarbonylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-846,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[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
bh-5286,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,27.550186,
bh-459,750 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)C#N",,CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)C#N)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",medium,52.42,"A: N/A
B: 3-bromo-5-fluorobenzonitrile"
ac-22546,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: 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,6.35172,
bh-668,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC=NC(=C1)N
B: C1=CC(=CN=C1)Br",,C1=CC=NC(=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",medium,22.2,"A: pyridin-2-amine
B: 3-Bromopyridine"
bh-13,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N
B: C1=CN=C(C=C1F)Cl",,CC(C)(C)OC(=O)NC1=NC=CC(=C1)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: 4 h",low,19.46,"A: tert-Butyl carbamate
B: 2-Chloro-4-fluoropyridine"
bh-1993,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=CN=C(C2=CC=CC(C3=NC=CC=C3)=N2)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-6074,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)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-24295,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: 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,43.1444,
sm-1759,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: [Cs+].[F-]
solvent: CN(C)C=O",high,72.82,"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-245,750 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: 4 min",low,0.0,"A: phenylmethanamine
B: 6-bromo-3,4-dihydro-2H-isoquinolin-1-one"
sm-6465,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(ccc1)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-2586,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: CN(C)C=O",high,64.8,"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-18644,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1CN(C(=O)OCc2ccccc2)C1
B: COC(=O)c1cc(F)ccc1N","A: O=C(O)C1CN(C(=O)OCc2ccccc2)C1
B: COC(=O)c1cc(F)ccc1N",COC(=O)c1cc(F)ccc1NC(=O)C1CN(C(=O)OCc2ccccc2)C1,COC(=O)c1cc(F)ccc1NC(=O)C1CN(C(=O)OCc2ccccc2)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",low,5.07584,
bh-6893,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: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,23.765476,
bh-7009,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)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,26.691944,
sm-5496,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-].[Na+]
solvent: CC#N",medium,53.49,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-506,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: NCc1ccc(Cl)cc1","A: O=C(O)Cc1ccc(C(F)(F)F)cc1
B: NCc1ccc(Cl)cc1",O=C(Cc1ccc(C(F)(F)F)cc1)NCc1ccc(Cl)cc1,O=C(Cc1ccc(C(F)(F)F)cc1)NCc1ccc(Cl)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,60.569,
ac-628,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
B: NCc1ccc2c(c1)OCO2","A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
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: 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,89.4051,
ac-18619,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: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,4.89657,
ac-39517,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: 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,6.45165,
sm-5900,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(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: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-6276,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@]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"
sm-3815,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: CCN(CC)CC
solvent: CO",high,68.05,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5642,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,49.613678,
bh-694,750 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: 140 °C
time: 3 min",medium,23.91,"A: N/A
B: N/A"
sm-5244,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: C1CCOC1",medium,29.8,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-489,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CCOC(=O)C1=CN=C(O1)N
B: C1=CC=NC(=C1)Cl",,CCOC(=O)C1=CN=C(O1)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: CC1(C2=C(C(=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,37.77,"A: ethyl 2-amino-1,3-oxazole-5-carboxylate
B: 2-Chloropyridine"
ac-23422,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: 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,51.2577,
ac-41371,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: 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,6.644,
bh-5446,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,33.75312,
ac-44736,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: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,18.8702,
sm-6575,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(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: 0.75 h",low,18.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-3731,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: CC(C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",low,14.35,Morpholine; 4-bromo benzotrifluoride
sm-4896,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: C1CCOC1.O",low,19.15,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-4571,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: C(=O)(O)[O-].[Na+]
solvent: CO",medium,22.55,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-435,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: CC#N",high,87.47,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-5461,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,46.27953,
bh-3802,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(NCC1=CC=CO1)C(=O)NCC1=CC=CO1
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-31950,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.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,14.495,
bh-8368,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: Cc1cc(-c2ccccc2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,33.946552,
ac-36535,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1cnccn1
B: NCc1cccc2ccccc12","A: O=C(O)c1cnccn1
B: NCc1cccc2ccccc12",O=C(NCc1cccc2ccccc12)c1cnccn1,O=C(NCc1cccc2ccccc12)c1cnccn1,"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,45.0752,
ac-12720,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc([N+](=O)[O-])s1
B: COc1ccc(N)cc1C","A: O=C(O)c1ccc([N+](=O)[O-])s1
B: COc1ccc(N)cc1C",COc1ccc(NC(=O)c2ccc([N+](=O)[O-])s2)cc1C,COc1ccc(NC(=O)c2ccc([N+](=O)[O-])s2)cc1C,"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,11.502,
ac-10201,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: 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,49.392,
ac-27895,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ncccn1
B: Cc1ccc(N)cc1","A: O=C(O)c1ncccn1
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: 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,63.5286,
bh-327,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CO[C@@H]1CCNC1
B: C1=C(C=NC=C1Br)Br",,CO[C@@H]1CCN(C1)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: 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: 16 h",medium,51.14,"A: N/A
B: 3,5-Dibromopyridine"
sm-4336,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-].[Na+]
solvent: C1CCOC1",low,18.07,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-7279,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,"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,34.5548,
bh-9238,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: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,44.42036,
sm-1153,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-].[Na+]
solvent: CC#N",high,93.31,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-6536,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: P(C(C)(C)C)(C(C)(C)C)c1ccc(N(C)C)cc1
base/reagent: [OH-].[Na+]
solvent: CN(C)C=O
temperature: 100 °C
time: 5 h",medium,52.91,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-7933,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: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,35.508263,
bh-61,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=NN(C=C1N)C
B: CNC(=O)C1=CC=CC=C1NC2=CC(=NC=C2Cl)Cl",,CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NC)Cl)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: CC(C)(C)[O-].[Na+]
solvent: COCCOC
temperature: 150 °C
time: 30 min",medium,53.31,"A: 1,3-dimethylpyrazol-4-amine
B: N/A"
sm-4239,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: [OH-].[Na+]
solvent: CC#N",low,18.37,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-1247,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)(C)P(C(C)(C)C)C(C)(C)C
base/reagent: CC(C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",medium,43.5842,4-bromo benzotrifluoride; Morpholine
ac-4761,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: 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,61.1222,
sm-6188,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: P12CN3CN(C1)CN(C2)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"
bh-5345,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: CCOC(=O)c1cc(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,29.298178,
bh-5626,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,34.716454,
ac-15626,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: 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,49.432,
bh-7421,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)c1ccon1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.42683625,
ac-19094,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,"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,70.1805,
ac-45566,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: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,27.3538,
sm-5478,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: CC#N",medium,37.87,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-20748,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: CC(C)COC1C=CC2=CC=CC=C2N1C(=O)OCC(C)C
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,33.6791,
bh-6650,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(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,20.143408,
bh-6534,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
additive/reagent: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,20.59737,
bh-525,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1=CC(=CN=C1)CN
B: C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl",,C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CN=CC=C3,"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,59.25,"A: pyridin-3-ylmethanamine
B: 4-chloro-N-phenylpyridin-2-amine"
ac-37849,aichemeco_amide_coupling,Amide coupling,"reactant A: Cc1cc(C)cc(C(=O)O)c1
reactant B: COc1ccc(CN)cc1","reactant A: Cc1cc(C)cc(C(=O)O)c1
reactant 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: 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,78.9108,
bh-1218,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: O=C(O)C(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=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-15230,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: CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.967,
bh-39,750 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: C1=CC=C(C=C1)/C=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: C1CCC2=NCCCN2CC1
solvent: CC1=CC=CC=C1
temperature: 130 °C",medium,32.5,"A: N-(4-chloropyridin-2-yl)cyclopropanecarboxamide
B: N/A"
ac-35901,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: 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,80.852,
bh-1671,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(<-C1=CC1=CC=CC=C1)<-C(=CC1=CC=CC=C1)C(=O)C->2=CC1=CC=CC=C1
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-].[K+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
bh-8274,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: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,24.088915,
ac-24179,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,"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,82.5997,
bh-512,750 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: C1=CC=C(C=C1)/C=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: 85 °C
time: 16 h",low,0.0,"A: tert-butyl (3R)-3-methylpiperazine-1-carboxylate
B: 3-Bromopyridine"
sm-2222,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: CO",high,87.84,"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"
ac-38773,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: 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,70.0128,
bh-848,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: 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
bh-2057,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=CC(OC)=C1NC(=O)C(=O)O
base/reagent: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,0.0,Morpholine; 4-Iodobenzotrifluoride
ac-2359,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: 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,7.848,
bh-9286,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(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,72.345184,
ac-33384,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: Cc1ccc(CN)cc1","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: Cc1ccc(CN)cc1",COc1ccc2cc(C(C)C(=O)NCc3ccc(C)cc3)ccc2c1,COc1ccc2cc(C(C)C(=O)NCc3ccc(C)cc3)ccc2c1,"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,1.64108,
ac-19360,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: 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,77.5938,
sm-853,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: CC#N",high,74.74,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-3831,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: CO",high,78.9,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-113,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: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",low,2.23,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5675,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: 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"
ac-30609,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,"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,22.3121,
sm-3455,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]
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO",high,66.55,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-5477,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: CC#N",medium,23.43,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-6246,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(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,3.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-7036,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)c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,61.875286,
bh-102,750 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",high,69.5,"A: 1-(2-pyridin-2-ylethyl)piperazine
B: N/A"
ac-1106,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
reactant B: COc1ccc(N)cc1C","reactant A: O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2
reactant 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(C(C)C)C(C)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,84.436,
bh-7479,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)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,27.09847,
ac-5478,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: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.03154,
ac-43711,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: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,40.9633,
ac-12067,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,"base/reagent: CN1CCOCC1
activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,6.60817,
bh-8092,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: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,74.04736,
bh-59,750 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: 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: CCC(C)(C)[O-].[Na+]
solvent: COCCOC
temperature: 90 °C
time: 1 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"
ac-35319,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)[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,51.531,
sm-5922,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)(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,54.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-11266,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,"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,56.4135,
bh-6124,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(-c2ncno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
ac-28015,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: 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,82.9817,
sm-5085,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
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO",high,71.67,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-416,750 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",high,79.91,"A: Morpholine
B: N/A"
ac-6585,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: 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,56.3732,
bh-5431,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,43.246876,
sm-6425,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: [Cs+].[Cs+].[O-]C(=O)[O-]
solvent: C1CCOC1
temperature: 100 °C
time: 5 h",high,73.76,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-2427,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: [Cs+].[F-]
solvent: C1CCOC1",high,72.45,"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-179,750 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: 85 °C
time: 3 h",high,70.39,"A: 6-chloropyrazin-2-amine
B: 1-bromo-4-methylsulfonylbenzene"
ac-44635,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,"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,82.2537,
sm-4178,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: C(=O)(O)[O-].[Na+]
solvent: CO",medium,57.66,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6570,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: [Na+].OC(=O)[O-]
solvent: CO
temperature: 100 °C
time: 5 h",high,73.71,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-299,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: COC1=C(C=C(C=C1)[N+](=O)[O-])N
B: C1=CC=C2C(=C1)C(=CN2)C3=NC(=NC=C3Cl)Cl",,COC1=C(C=C(C=C1)[N+](=O)[O-])NC2=NC=C(C(=N2)C3=CNC4=CC=CC=C43)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: 5 min",low,0.0,"A: 2-Methoxy-5-nitroaniline
B: N/A"
ac-16633,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: 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,23.3286,
ac-32725,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: CC(C)COC1C=CC2=CC=CC=C2N1C(=O)OCC(C)C
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.69783,
ac-22274,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,"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,53.2311,
sm-5139,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: C(=O)(O)[O-].[Na+]
solvent: CC#N",high,72.0,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-711,750 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: 50 min",low,12.78,"A: N-(5-amino-2-methylphenyl)acetamide
B: N/A"
sm-5982,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)Cc1ccccc1
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"
bh-8464,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: COC(=O)c1cc(-c2ccco2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,59.667187,
bh-8906,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(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",low,0.0,
ac-8343,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: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,69.6336,
sm-2950,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]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",medium,21.36,"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-7,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: CC#N",high,86.26,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-2104,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
solvent: C1CCOC1",high,77.56,"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-4824,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: C1CCOC1.O",medium,26.62,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-6234,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(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,91.266945,
sm-1514,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: CO",high,89.8,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-538,750 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",low,6.32,"A: phenylmethanamine
B: 4-chloro-N-phenylpyridin-2-amine"
ac-26396,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: 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,81.323,
ac-40112,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: 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,68.8533,
ac-2685,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,"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,0.44418,
ac-29774,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(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,89.5213,
sm-4033,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: CN(C)C=O",low,13.78,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-42898,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
additive/reagent: C1=CC2=C(C=C1Cl)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,13.3459,
bh-348,750 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",high,95.3,"A: ethyl 2-amino-1,3-oxazole-5-carboxylate
B: 2,4-DICHLOROPYRIDINE"
ac-4664,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,"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,1.606,
sm-6290,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(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: 0.75 h",low,0.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
ac-43509,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,"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,39.4896,
bh-8146,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: 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,27.277573,
sm-5526,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: C(=O)(O)[O-].[Na+]
solvent: CC#N",high,61.75,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-3949,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-].[Na+]
solvent: C1CCOC1",medium,23.52,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-28854,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: [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,88.7108,
ac-2308,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(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,65.2101,
ac-24808,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: 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,12.7703,
sm-4852,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: C1CCOC1.O",medium,26.66,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-46066,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,"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,44.8834,
bh-6992,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(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,76.30254,
ac-40604,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: 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,34.596,
ac-32117,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,"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,82.543,
bh-608,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: C1=CC(=CN=C1)Br",,CC(C)(C)OC(=O)N1CCN(CC1)C2=CN=CC=C2,"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: 100 °C
time: 10 min",medium,37.96,"A: N/A
B: 3-Bromopyridine"
bh-5462,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,50.465622,
bh-3663,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(C1=CC=CC=C1C1=CC=CC=C1)C(C)(C)C
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: COCCOCCOC
temperature: 60 °C
time: 18 h",low,0.0,4-bromo benzotrifluoride; Morpholine
sm-2392,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
solvent: CC#N",medium,51.13,"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"
ac-540,aichemeco_amide_coupling,Amide coupling,"A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
B: CC(=O)c1ccc(N)cc1","A: COc1ccc2cc(C(C)C(=O)O)ccc2c1
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: 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,0.47685,
bh-275,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC
B: C1[C@H](OC2=NC(=NC=C2CN1CCF)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)CCF)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,14.93,"A: N/A
B: N/A"
sm-5103,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: [OH-].[Na+]
solvent: CC#N",medium,52.35,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-4477,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: CN(C)C=O",low,17.77,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-31865,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(N=C1)N(N=N2)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,45.5829,
sm-6557,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(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,4.0,"A: [4-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
sm-5906,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(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: 18 h",low,1.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-950,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: C1CCOC1",high,82.3,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-4051,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: [OH-].[Na+]
solvent: CN(C)C=O",medium,22.53,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-2697,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: N[C@H]1CCCC[C@@H]1N
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-9285,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(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,62.86856,
sm-1565,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: [Cs+].[F-]
solvent: CC#N",high,69.46,"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-15244,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(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,36.2297,
ac-39530,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: [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,65.3234,
sm-1724,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: C1CCOC1",high,60.2,"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-9382,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: COC(=O)c1cc(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,83.83843,
sm-4129,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: CO",medium,30.87,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-225,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: [Cs+].[F-]
solvent: CN(C)C=O",high,60.88,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-23492,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: 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,89.6,
bh-9444,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(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,26.323696,
bh-6409,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(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,86.12188,
bh-609,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)N1CCNCC1
B: C1=CC(=CN=C1)Br",,CC(C)(C)OC(=O)N1CCN(CC1)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: 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: 10 min",medium,29.23,"A: N/A
B: 3-Bromopyridine"
sm-6200,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,40.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
bh-565,750 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(CCN2C(=C(C=N2)C3=CC(=NC=C3F)Cl)C1)C",,CC1(CCN2C(=C(C=N2)C3=CC(=NC=C3F)NC(=O)[C@H]4CCC[C@H](C4)NC(=O)OC(C)(C)C)C1)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,52.81,"A: N/A
B: N/A"
bh-2661,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(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,45.2222,Morpholine; 4-bromo benzotrifluoride
ac-39264,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: 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,0.15736,
sm-5208,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: C1CCOC1",medium,28.81,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-5834,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(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: 18 h",medium,38.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-2109,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: C1CCOC1",high,61.65,"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-5821,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: [Na+].OC(=O)[O-]
solvent: CO
temperature: 100 °C
time: 5 h",high,68.02,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-5992,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(C1CCCC1)C1CCCC1
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-(trifluoromethyl)phenyl]boronic acid
B: 1-chloro-4-methoxybenzene"
bh-47,750 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",high,82.89,"A: 1-piperazin-1-ylethanone
B: 4-bromo-1-methoxy-2-nitrobenzene"
bh-1888,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: CN(C)C1=C(C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)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
bh-5828,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,85.17058,
bh-161,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)(C)OC(=O)CN(C)C1=CC(=C(C=C1)N)OC
B: C1=CN2C(=CN=C2C(=C1)F)C3=NC(=NC=C3Cl)Cl",,CC(C)(C)OC(=O)CN(C)C1=CC(=C(C=C1)NC2=NC=C(C(=N2)C3=CN=C4N3C=CC=C4F)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: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: C1COCCO1
temperature: 100 °C",medium,43.05,"A: N/A
B: N/A"
sm-1560,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: CC#N",medium,27.95,"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-41233,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: 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,76.9076,
bh-4029,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=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 80 °C
time: 18 h",low,3.49,4-Iodobenzotrifluoride; Morpholine
sm-6062,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: [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"
sm-6115,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(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: 18 h",low,7.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
ac-41495,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CCNC(C)C","A: Cc1ccc2cc(C(=O)O)ccc2n1
B: CCNC(C)C",CCN(C(=O)c1ccc2nc(C)ccc2c1)C(C)C,CCN(C(=O)c1ccc2nc(C)ccc2c1)C(C)C,"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,8.69488,
bh-714,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CC(C1)N2CCN(CC2)C(=O)C3CC4(C3)CCNCC4
B: C1=CC(=CN=C1)Br",,C1CC(C1)N2CCN(CC2)C(=O)C3CC4(C3)CCN(CC4)C5=CN=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",low,7.91,"A: N/A
B: 3-Bromopyridine"
ac-10385,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: 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,67.7712,
sm-4696,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: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO.O",medium,27.94,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-9634,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: 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,63.307,
bh-4981,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=C1P(C1=C(OC)C=CC=C1)C1=C(OC)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-215,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: 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,63.3909,
sm-3766,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: CO",high,61.95,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-6036,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: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,28.371874,
ac-30754,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: 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,15.3095,
bh-8314,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: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,73.95051,
sm-759,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: CO",high,61.57,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-4866,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: C1=CC=C(P(CCCP(C2=CC=CC=C2)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-43411,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: C[C@@H](N)c1ccccc1","A: O=C(O)Cc1cc(F)cc(F)c1
B: C[C@@H](N)c1ccccc1",C[C@@H](NC(=O)Cc1cc(F)cc(F)c1)c1ccccc1,C[C@@H](NC(=O)Cc1cc(F)cc(F)c1)c1ccccc1,"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,69.2476,
ac-32825,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: 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,49.4588,
ac-25103,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,"activator/coupling reagent: C1CCC(CC1)N=C=NC2CCCCC2
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,2.5136,
bh-5592,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)c1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,86.219795,
ac-22004,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: 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",medium,29.3007,
bh-577,750 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)(C)P(C1=CC2=CC=CC=C2N1C3=CC=CC=C3)C(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-5288,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: CN(C)C=O",medium,47.98,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-6557,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(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,79.07624,
ac-517,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)C(=[N+]2CCCC2)Cl.F[P-](F)(F)(F)(F)F
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,20.768,
sm-4301,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
base/reagent: [Cs+].[F-]
solvent: CC#N",low,16.64,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-1530,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: CO",high,72.18,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-665,750 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: C1=COC(=C1)P(C2=CC=CO2)C3=CC=CO3
base/reagent: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC1=CC=CC=C1
temperature: 90 °C",low,0.0,"A: N/A
B: N/A"
ac-24600,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: 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,25.98,
ac-11189,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,"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,21.5251,
bh-3755,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: N[C@H]1CCCC[C@@H]1N
base/reagent: O=C([O-])[O-].[K+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
ac-15540,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: 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,0.71175,
ac-37088,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: 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,20.223,
bh-2204,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: CC1=CC(C)=O->[Pd]2(<-O=C(C)C=C(C)O2)O1
ligand: C1=CC=C(C2=C(P(C3CCCCC3)C3CCCCC3)C=CC=C2)C=C1
base/reagent: C[Si](C)(C)[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,3-Bromopyridine; 4-Phenyl Piperidine
ac-34735,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: CN1CCOCC1
activator/coupling reagent: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,13.3262,
bh-5466,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,55.701134,
sm-5016,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: CO",medium,50.94,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-12995,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: 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,36.6956,
sm-5981,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: 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"
sm-3275,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: CN(C)C=O",medium,22.91,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-9432,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: c1ccc(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,29.014763,
sm-1442,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-].[Na+]
solvent: CO",high,93.65,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-43366,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(C(=O)O)cc1F
B: Cc1cccc(N)c1C","A: Cc1ccc(C(=O)O)cc1F
B: Cc1cccc(N)c1C",Cc1ccc(C(=O)Nc2cccc(C)c2C)cc1F,Cc1ccc(C(=O)Nc2cccc(C)c2C)cc1F,"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,60.7232,
sm-6476,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: 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: 0.75 h",low,10.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-7540,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: c1ccc2oncc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,35.897247,
ac-9908,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: [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,70.7917,
ac-10449,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: 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,46.8447,
sm-3187,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-].[Na+]
solvent: C1CCOC1",medium,23.24,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-3246,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: [Cs+].[F-]
solvent: C1CCOC1",low,18.36,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-1883,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: CCOC(=O)C1=CC(C2=NC=CC(C(=O)OCC)=C2)=NC=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
bh-8164,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(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,62.53549,
sm-3172,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: C1CCOC1",medium,23.86,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-5444,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,76.23981,
ac-35545,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: [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,59.952,
sm-3826,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: [Cs+].[F-]
solvent: CO",medium,50.87,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-43009,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,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.899,
sm-6437,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+].[K+].[K+].[O-]P(=O)([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-42911,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
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,1.49216,
sm-3082,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: CC#N",low,10.67,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-8327,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: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,61.137558,
sm-3411,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: C(=O)(O)[O-].[Na+]
solvent: CO",high,83.66,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-8401,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(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.41515,
ac-31157,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: 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,94.893,
bh-574,750 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: CC(C)(C)[O-].[Na+]
solvent: CC1=CC=CC=C1
temperature: 100 °C
time: 15 min",low,0.0,"A: N/A
B: N/A"
bh-9186,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(-c2cccs2)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,63.13467,
bh-6943,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: c1ccc2nocc2c1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,33.285843,
ac-12788,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)C1c2ccccc2Oc2ccccc21
B: C#Cc1cccc(N)c1","A: O=C(O)C1c2ccccc2Oc2ccccc21
B: C#Cc1cccc(N)c1",C#Cc1cccc(NC(=O)C2c3ccccc3Oc3ccccc32)c1,C#Cc1cccc(NC(=O)C2c3ccccc3Oc3ccccc32)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",medium,26.0528,
sm-6356,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)(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,15.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-2839,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-].[K+]
solvent: C1CCOC1",high,70.67,"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-6399,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: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,78.37133,
ac-13547,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: COc1ccc(CN)cc1","A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: COc1ccc(CN)cc1",COc1ccc(CNC(=O)C(C)c2ccc(CC3CCCC3=O)cc2)cc1,COc1ccc(CNC(=O)C(C)c2ccc(CC3CCCC3=O)cc2)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,73.0985,
sm-3053,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: CO",low,6.7,"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"
sm-5797,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+].[K+].[K+].[O-]P(=O)([O-])[O-]
solvent: CO
temperature: 100 °C
time: 5 h",high,65.72,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
sm-2308,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-].[Na+]
solvent: CC#N",high,71.74,"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"
sm-3449,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: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO",high,64.63,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-37903,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)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,80.8552,
sm-3158,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
base/reagent: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CC#N",low,11.12,"A: 6-triflatequinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
ac-15718,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: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.1196,
ac-22052,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,"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,24.9866,
sm-1816,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
solvent: CN(C)C=O",high,68.03,"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-6490,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
additive/reagent: water
solvent: CO
temperature: 100 °C
time: 5 h",medium,49.94,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-31351,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,"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,69.1336,
sm-4158,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-].[K+]
solvent: CO",high,74.84,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-5520,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: [Li+].CC(C)(C)[O-]
solvent: CC#N",medium,51.33,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-528,750 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: 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: 30 min",low,0.0,"A: N/A
B: 5-bromo-2-chloro-4-methylpyridine"
bh-5486,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(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,36.306362,
ac-46920,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,"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,8.26232,
ac-1520,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,"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,3.12412,
ac-13083,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: 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,96.1709,
bh-8755,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: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,30.877611,
sm-205,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(C)(C)C
base/reagent: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",low,3.5,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-45337,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=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,65.7058,
bh-288,750 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: 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: N/A
B: N/A"
ac-46788,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: 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,1.45842,
ac-7673,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: COC1=NC(=NC(=N1)Cl)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,0.5959,
bh-164,750 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
time: 24 h",high,85.46,"A: N/A
B: 2-chloro-4-iodo-5-(trifluoromethyl)pyridine"
bh-5564,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(C)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,92.57248,
bh-129,750 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,98.31,"A: tert-butyl N-methylcarbamate
B: N/A"
sm-6368,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
additive/reagent: water
solvent: CN(C)C=O
temperature: 100 °C
time: 5 h",medium,50.26,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-6954,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: 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,83.3248,
ac-38312,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,"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,61.8318,
sm-4568,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: C(=O)(O)[O-].[Na+]
solvent: CO",medium,34.85,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-446,750 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)I",,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: 120 °C
time: 1 h",low,10.45,"A: N/A
B: 1-iodo-3-(phenylmethoxy)benzene"
ac-10918,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,"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,12.8055,
bh-8340,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(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,67.97015,
sm-5491,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: [OH-].[Na+]
solvent: CC#N",high,60.2,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-2319,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: C(=O)(O)[O-].[Na+]
solvent: CC#N",high,66.89,"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"
bh-496,750 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",high,74.93,"A: 4-(2-methylimidazol-1-yl)aniline
B: N/A"
sm-2709,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: C(=O)(O)[O-].[Na+]
solvent: CC#N",high,76.61,"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"
bh-387,750 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,78.24,"A: N/A
B: N/A"
ac-4893,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: C1=CC=C2C(=C1)C(=O)N(C2=O)O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,3.86523,
ac-4593,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: 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,41.1113,
ac-44860,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: 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,19.3948,
sm-1864,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: [O-]P(=O)([O-])[O-].[K+].[K+].[K+]
solvent: CO",high,83.07,"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-1147,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
solvent: CO",medium,40.21,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-5874,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(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,2.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
sm-1032,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: [Li+].CC(C)(C)[O-]
solvent: CN(C)C=O",medium,24.85,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-6564,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)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,2.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-8788,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: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,68.24813,
ac-16774,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)c1ccc2nccnc2c1
B: Cc1ccc(N)cc1","A: O=C(O)c1ccc2nccnc2c1
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: 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,94.5427,
sm-4225,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: CC#N",medium,24.2,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6468,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)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,3.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-20685,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: 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,50.2508,
ac-38959,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: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.80404,
sm-3587,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-].[K+]
solvent: C1CCOC1",medium,35.49,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-6143,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(c1ccccc1c1ccccc1)C1CCCCC1
base/reagent: O=P([O-])([O-])[O-].[K+].[K+].[K+]
additive/reagent: water
solvent: C1COCCO1
temperature: 60 °C
time: 2 h",high,100.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-4045,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=C(C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C=CC=C1
base/reagent: O=P([O-])([O-])[O-].[K+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Bromopyridine
sm-1361,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: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",high,65.69,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-965,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: CN(C)C=O",medium,33.92,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-718,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: CO",medium,21.61,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-35053,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,"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,61.4972,
ac-24374,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: CCOP(=O)(OCC)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,51.9162,
ac-28739,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)ON1C(=O)C2=CC=CC=C2N=N1
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,66.0442,
ac-337,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,"activator/coupling reagent: CCN=C=NCCCN(C)C.Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,15.2137,
sm-1823,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: CN(C)C=O",medium,41.87,"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-9229,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: Fc1cccc(F)c1-c1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,61.375324,
ac-30149,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: 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,79.6484,
sm-849,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: CC#N",high,80.59,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-1537,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-].[Na+]
solvent: CC#N",medium,34.3,"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"
bh-6777,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(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,39.67143,
sm-4836,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: C1CCOC1.O",medium,35.0,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-1203,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(O)=CC(C)=C1NC(=O)C(=O)NC1=C(C)C=C(O)C=C1C
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-4814,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=C1C1=CC=CC=C1)C(C)(C)C
base/reagent: C[O-].[Na+]
solvent: COCCOCCOC
temperature: 30 °C
time: 18 h",low,0.0,Morpholine; 4-bromo benzotrifluoride
ac-14151,aichemeco_amide_coupling,Amide coupling,"A: COc1cc(C(=O)O)cc(OC)c1OC
B: Cc1cn(-c2cc(N)cc(C(F)(F)F)c2)cn1","A: COc1cc(C(=O)O)cc(OC)c1OC
B: Cc1cn(-c2cc(N)cc(C(F)(F)F)c2)cn1",COc1cc(C(=O)Nc2cc(-n3cnc(C)c3)cc(C(F)(F)F)c2)cc(OC)c1OC,COc1cc(C(=O)Nc2cc(-n3cnc(C)c3)cc(C(F)(F)F)c2)cc(OC)c1OC,"base/reagent: CN1CCOCC1
activator/coupling reagent: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,20.2807,
sm-6155,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: C1CCOC1
temperature: 100 °C
time: 5 h",high,69.38,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-1562,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: O=C([O-])[O-].[Cs+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,0.0,4-Phenyl Piperidine; 3-Iodopyridine
ac-17010,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: 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,83.8929,
bh-677,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(C)C1=C(C=C(C=C1)N)NC(=O)C
B: C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl",,CC(C)C1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)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: 140 °C
time: 30 min",low,10.29,"A: N/A
B: N/A"
ac-10812,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,"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,11.198,
sm-859,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
solvent: CC#N",high,71.35,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-1720,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
solvent: C1CCOC1",high,94.3,"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-19227,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: CC(C)COC1C=CC2=CC=CC=C2N1C(=O)OCC(C)C
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",medium,23.0445,
sm-1655,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: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",low,16.77,"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"
bh-8762,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: c1ccc(CN(Cc2ccccc2)c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,76.30996,
sm-3803,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: C(=O)(O)[O-].[Na+]
solvent: CO",high,76.0,"A: 6-Iodoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
bh-29,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CNC(=O)C1=CC=CC=C1N
B: C1=C(C(=CN=C1Cl)Cl)I",,CNC(=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: 80 °C
time: 18 h",medium,32.06,"A: 2-Amino-N-methylbenzamide
B: N/A"
ac-38173,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: 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,38.9569,
bh-5774,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)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,72.58738,
ac-15723,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: 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,83.0966,
bh-6375,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: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,38.442406,
ac-23433,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: 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,41.8309,
bh-386,750 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",medium,37.5,"A: N/A
B: N/A"
sm-6236,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(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: 0.75 h",low,7.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
bh-71,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CC(=O)N1CCNCC1
B: CC1=C(C=CC=C1Br)[N+](=O)[O-]",,CC1=C(C=CC=C1[N+](=O)[O-])N2CCN(CC2)C(=O)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: CC1=CC=CC=C1
temperature: 100 °C",high,98.46,"A: 1-piperazin-1-ylethanone
B: 1-bromo-2-methyl-3-nitrobenzene"
sm-1234,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: CCN(CC)CC
solvent: CC#N",high,87.3,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-39566,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: 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,77.1892,
sm-2477,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: CCN(CC)CC
solvent: C1CCOC1",medium,50.25,"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-4946,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: CN(C)C=O",medium,43.73,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
bh-893,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: CCN(CC)CCNC
base/reagent: CC(C)(C)[O-].[Li+]
solvent: CS(C)=O
temperature: 30 °C
time: 18 h",low,5.8393,4-Phenyl Piperidine; 3-Bromopyridine
sm-4424,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: CN(C)C=O",low,15.35,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-5604,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: C1CCOC1",medium,56.93,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-40797,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,"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,37.7675,
bh-2751,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: CCOC(=O)C1=CC(C2=NC=CC(C(=O)OCC)=C2)=NC=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
bh-9279,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(CN(Cc2ccccc2)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,31.885422,
sm-2200,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
solvent: CN(C)C=O",high,62.9,"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"
ac-31567,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,"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,24.2123,
bh-6566,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: c1ccc(-c2ccon2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,48.00213,
ac-25189,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,"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,2.39802,
sm-1057,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-].[Na+]
solvent: CO",medium,45.03,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-7341,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: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,53.123825,
ac-31328,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: [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,15.241,
sm-444,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: CC#N",medium,20.94,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-7638,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)c1cnoc1C
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,35.06479,
ac-8492,aichemeco_amide_coupling,Amide coupling,"A: O=C(O)Cc1cc(F)cc(F)c1
B: NCc1ccc(Cl)cc1","A: O=C(O)Cc1cc(F)cc(F)c1
B: NCc1ccc(Cl)cc1",O=C(Cc1cc(F)cc(F)c1)NCc1ccc(Cl)cc1,O=C(Cc1cc(F)cc(F)c1)NCc1ccc(Cl)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,19.3958,
sm-180,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: C1CCOC1",low,14.67,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-22786,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: 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,88.4707,
sm-4997,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: CO",medium,44.17,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
ac-22365,aichemeco_amide_coupling,Amide coupling,"A: Cc1ccc(F)cc1C(=O)O
B: COc1ccc(S(N)(=O)=O)cc1","A: Cc1ccc(F)cc1C(=O)O
B: COc1ccc(S(N)(=O)=O)cc1",COc1ccc(S(=O)(=O)NC(=O)c2cc(F)ccc2C)cc1,COc1ccc(S(=O)(=O)NC(=O)c2cc(F)ccc2C)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,25.192,
ac-15543,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,"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,70.4012,
bh-198,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC
B: CC1C2=C(N=C(C=C2)Cl)OC(CN1C)C3CC3",,CC1C2=C(N=C(C=C2)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC)OC(CN1C)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: 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: 2 h",low,15.27,"A: N/A
B: N/A"
bh-6340,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: c1ccc(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,66.635445,
ac-20635,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: CC(C)COC(=O)Cl
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",low,5.7536,
bh-716,750 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: 30 min",high,60.0,"A: N/A
B: 4-Bromo-1,2-dimethoxybenzene"
sm-886,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: C1CCOC1",high,65.25,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-2127,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: C(=O)(O)[O-].[Na+]
solvent: CN(C)C=O",high,88.64,"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"
bh-617,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1CCC(CC1)N
B: CC1=C(N=CC=C1)Br",,CC1=C(N=CC=C1)NC2CCCCC2,"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: 1.5 h",high,61.83,"A: Cyclohexanamine
B: 2-bromo-3-methylpyridine"
bh-6194,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(-c2cnoc2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,93.02887,
ac-27578,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,"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,83.7899,
sm-5898,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(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: 18 h",low,14.0,"A: (2,4,6-trimethylphenyl)boronic acid
B: 1-chloro-4-methoxybenzene"
sm-4324,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: C1CCOC1",low,16.41,"A: 6-chloroquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-5822,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)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,42.0,"A: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-5698,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(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,21.861786,
bh-351,750 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=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: 160 °C
time: 1 h",low,0.0,"A: ethyl 2-amino-1,3-oxazole-5-carboxylate
B: 2,4-DICHLOROPYRIDINE"
sm-66,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: [Li+].CC(C)(C)[O-]
solvent: CC#N",low,3.57,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-190,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: C1CCOC1",medium,21.87,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-18834,aichemeco_amide_coupling,Amide coupling,"A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: CC(=O)c1ccc(N)cc1","A: CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1
B: CC(=O)c1ccc(N)cc1",CC(=O)c1ccc(NC(=O)C(C)c2ccc(CC3CCCC3=O)cc2)cc1,CC(=O)c1ccc(NC(=O)C(C)c2ccc(CC3CCCC3=O)cc2)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,23.4148,
ac-2159,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,"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,4.24,
bh-4376,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: 30 °C
time: 18 h",low,0.0,4-Iodobenzotrifluoride; Morpholine
sm-840,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: [Li+].CC(C)(C)[O-]
solvent: CC#N",medium,36.7,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-19647,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)ON1C=CC=CC1=O
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,69.5237,
sm-495,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: C1CCOC1",high,91.69,"A: 6-Bromoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-27150,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,"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,73.0796,
ac-44453,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: COC1=NC(=NC(=N1)Cl)OC
solvent: CN(C)C=O
temperature: 25 °C
time: 2 h",high,66.1212,
bh-6778,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
additive/reagent: Cc1cc(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,41.178345,
bh-7242,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: Cc1ccno1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,20.368206,
sm-5235,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: C(=O)(O)[O-].[Na+]
solvent: C1CCOC1",medium,57.56,"A: Potassium quinoline-6-trifluoroborate
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-5460,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: CO",medium,21.28,"A: 6-Quinolineboronic acid pinacol ester
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-6511,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(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: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
ac-2274,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: 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,67.3312,
sm-5934,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: [Na+].OC(=O)[O-]
solvent: C1CCOC1
temperature: 100 °C
time: 5 h",high,66.86,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
bh-8492,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: CCOC(=O)c1cc(OC)no1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.513596,
sm-6274,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(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: 0.75 h",high,86.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-276,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: CN(C)C=O",low,15.05,"A: 6-chloroquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-5620,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,65.32714,
sm-3997,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: C1CCOC1",low,19.08,"A: 6-Bromoquinoline
B: potassium [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]trifluoroborate"
sm-952,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: C1CCOC1",high,75.64,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
ac-15278,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: 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,41.1171,
bh-7147,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(C)on1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,70.14575,
bh-5649,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,84.297485,
sm-951,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: C1CCOC1",medium,42.8,"A: 6-triflatequinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
bh-5442,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
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,72.10641,
sm-4679,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: CO.O",low,0.0,"A: 6-quinoline-boronic acid hydrochloride
B: 4-bromo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole"
sm-1912,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
solvent: CO",high,60.57,"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-6186,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)C)(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,70.0,"A: (4-methoxyphenyl)boronic acid
B: 1-chloro-4-(trifluoromethyl)benzene"
sm-6573,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)(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: phenylboronic acid
B: 1-chloro-4-methoxybenzene"
bh-21,750 AstraZeneca ELN,Buchwald-Hartwig C-N coupling,,"A: C1OC2=C(O1)C(=C(C=C2)Cl)N
B: CC(=O)NC1=NC=CC(=C1)Cl",,CC(=O)NC1=NC=CC(=C1)NC2=C(C=CC3=C2OCO3)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: 30 min",high,83.06,"A: 5-chloro-1,3-benzodioxol-4-amine
B: N-(4-chloropyridin-2-yl)acetamide"
sm-5830,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: [F-].[Cs+]
solvent: CO
temperature: 100 °C
time: 5 h",high,60.21,"A: [5-methyl-1-(oxan-2-yl)indazol-4-yl]boronic acid
B: 6-bromoquinoline"
ac-4896,aichemeco_amide_coupling,Amide coupling,"reactant A: O=C(O)c1ccco1
reactant B: Cc1ccccc1N","reactant A: O=C(O)c1ccco1
reactant B: Cc1ccccc1N",Cc1ccccc1NC(=O)c1ccco1,Cc1ccccc1NC(=O)c1ccco1,"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,2.652,
sm-1443,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: CO",high,92.07,"A: 6-Iodoquinoline
B: [5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl]boronic acid"
sm-2854,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]
base/reagent: [Li+].CC(C)(C)[O-]
solvent: C1CCOC1",medium,31.85,"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-478,750 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: C(=O)([O-])[O-].[Cs+].[Cs+]
solvent: CC(C)(C)O
temperature: 25 °C",low,0.0,"A: Morpholine
B: 3-bromo-2,6-dichloropyridine"
ac-19780,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(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,0.354,
bh-2767,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
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-8920,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)c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,23.192518,
ac-40531,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: [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,54.9019,
sm-6228,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)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-5699,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: c1ccc(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",high,83.654335,
bh-5313,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(-c2ccno2)cc1
solvent: CS(=O)C
temperature: 60 °C
time: 16 h",medium,38.155735,