Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:11][C:10](=[O:12])[NH:9][C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].BrCCCCC(OC)=O>>[CH:17]1[CH:18]=[CH:19][C:14]([C:7]2([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[NH:11][C:10]([OH:12])=[N:9][C:8]2=[O:13])=[CH:15][CH:16]=1
Reactant: O=C1NC(=O)C(c2ccccc2)(c2ccccc2)N1
Agent: COC(=O)CCCCBr
Agent: [Na]
Product: O=C1N=C(O)NC1(c1ccccc1)c1ccccc1

Procedure:
Following the method of cook et al, Res. Comm. Chem. Path. Pharm. 5:767(1973), sodium diphenylhydantoin is reacted with methyl 5-bromovalerate followed by acid hydrolysis to yield the following: ##STR14##
Reaction SMILES: [O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:9]([O:11][C:12]([C:14]1[C:18]([CH3:19])=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22](Br)[CH:21]=2)[N:16]([CH3:27])[N:15]=1)=[O:13])[CH3:10].[O:28]1[C:32](B(O)O)=[CH:31][C:30]2[CH:36]=[CH:37][CH:38]=[CH:39][C:29]1=2>>[CH2:9]([O:11][C:12]([C:14]1[C:18]([CH3:19])=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:32]2[O:28][C:29]3[CH:39]=[CH:38][CH:37]=[CH:36][C:30]=3[CH:31]=2)[N:16]([CH3:27])[N:15]=1)=[O:13])[CH3:10]
Reactant: CCOC(=O)c1nn(C)c(-c2cccc(Br)c2)c1C
Reactant: OB(O)c1cc2ccccc2o1
Agent: O=P([O-])([O-])[O-]
Agent: [K+]
Product: CCOC(=O)c1nn(C)c(-c2ccccc2-c2cc3ccccc3o2)c1C
Yield: 73 %

Procedure:
In analogy to the procedure described in Example 14C] but with 2.8 eq of K3PO4, 5-(3-bromo-phenyl)-1,4-dimethyl-1H-pyrazole-3-carboxylic acid ethyl ester and benzo[b]furan-2-boronic acid gave 5-(3-benzofuran-2-yl-phenyl)-1,4-dimethyl-1H-pyrazole-3-carboxylic acid ethyl ester in 73% yield as light brown foam. MS: 361.4 (MH+).
Reaction SMILES: [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:27]=[CH:26][C:12]3[N:13]([C:16]4[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=O)=[CH:18][CH:17]=4)[CH:14]=[N:15][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1.[CH3:28][N:29]1[CH2:34][CH2:33][N:32]([CH2:35][C:36]2[CH:41]=[CH:40][C:39]([NH2:42])=[CH:38][C:37]=2[C:43]([F:46])([F:45])[F:44])[CH2:31][CH2:30]1>C(Cl)Cl.CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:27]=[CH:26][C:12]3[N:13]([C:16]4[CH:17]=[CH:18][C:19]([CH2:22][C:23]([NH:42][C:39]5[CH:40]=[CH:41][C:36]([CH2:35][N:32]6[CH2:31][CH2:30][N:29]([CH3:28])[CH2:34][CH2:33]6)=[C:37]([C:43]([F:46])([F:45])[F:44])[CH:38]=5)=[O:25])=[CH:20][CH:21]=4)[CH:14]=[N:15][C:11]=3[CH:10]=2)=[CH:7][CH:8]=1
Reactant: CN1CCN(Cc2ccc(N)cc2C(F)(F)F)CC1
Reactant: COc1ccc(-c2ccc3c(c2)ncn3-c2ccc(CC(=O)O)cc2)cc1
Solvent: CO
Solvent: ClCCl
Product: COc1ccc(-c2ccc3c(c2)ncn3-c2ccc(CC(=O)Nc3ccc(CN4CCN(C)CC4)c(C(F)(F)F)c3)cc2)cc1

Procedure:
The title compound is prepared as described in Example 1 but using {4-[5-(4-methoxy-phenyl)-benzoimidazol-1-yl]-phenyl}-acetic acid and 4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenylamine (WO 03/099771). Title compound: ES-MS: 613.9 [M+H]+; single peak at tR=3.56 min (System 1); Rf=0.10 (CH2Cl2/MeOH+1% NH3aq, 9:1).
Reaction SMILES: [C:1]([O:5][C:6](=[O:36])[NH:7][CH2:8][C:9]1[N:10]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:11](=[O:31])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:16][C:15]([C:25]1[S:26][CH:27]=[C:28]([NH2:30])[N:29]=1)=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].[C:37](Cl)(=[O:39])[CH3:38].O>CN(C)C(=O)C>[C:1]([O:5][C:6](=[O:36])[NH:7][CH2:8][C:9]1[N:10]([CH2:32][CH:33]([CH3:34])[CH3:35])[C:11](=[O:31])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:16][C:15]([C:25]1[S:26][CH:27]=[C:28]([NH:30][C:37](=[O:39])[CH3:38])[N:29]=1)=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2]
Reactant: CC(C)Cn1c(CNC(=O)OC(C)(C)C)c(-c2ccccc2)c2cc(-c3nc(N)cs3)ccc2c1=O
Reactant: CC(=O)Cl
Solvent: CC(=O)N(C)C
Solvent: O
Product: CC(=O)Nc1csc(-c2ccc3c(=O)n(CC(C)C)c(CNC(=O)OC(C)(C)C)c(-c4ccccc4)c3c2)n1
Yield: 82.3 %

Procedure:
A solution of tert-butyl[6-(4-amino-1,3-thiazol-2-yl)-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.20 g, 0.4 mmol) and acetyl chloride (0.04 ml, 0.6 mmol) in N,N-dimethylacetamide (10 ml) was stirred at room temperature for 2 h. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give tert-butyl{6-[4-(acetylamino)-1,3-thiazol-2-yl]-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl}methylcarbamate (0.18 g, 85.7%) as crystals.
Reaction SMILES: [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([NH:16][CH3:17])=[O:15])=[CH:12][N:11]=[C:10]([CH3:18])[CH:9]=2)=[C:4](F)[CH:3]=1.[H-].[Na+]>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:13](=[CH:12][N:11]=[C:10]([CH3:18])[CH:9]=3)[C:14](=[O:15])[N:16]([CH3:17])[C:4]=2[CH:3]=1
Reactant: CNC(=O)c1cnc(C)cc1-c1ccc(Cl)cc1F
Agent: [H-]
Agent: [Na+]
Solvent: C1CCOC1
Solvent: O
Product: Cc1cc2c(cn1)c(=O)n(C)c1cc(Cl)ccc21
Temperature: 25 °C
Reaction time: 15 h
Yield: 81.2 %

Procedure:
To a solution of 4-(4-chloro-2-fluorophenyl)-N,6-dimethylnicotinamide (520 mg, 1.86 mmol) in tetrahydrofuran (20 mL) at 0° C. was added NaH (224 mg, 5.60 mmol). The reaction mixture was brought to room temperature gradually and stirred at room temperature for 15 h. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (100 mL). The organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure to afford 8-chloro-2,6 dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (480 mg, 1.51 mmol, 81% yield) as a brick-red solid. LC/MS (ESI) m/e 259.0 [(M+H)+, calcd for C14H12ClN2O 259.05]; LC/MS retention time (method C): tR=1.91 min. 1H NMR (400 MHz, METHANOL-d4) δ ppm 9.41 (s, 1H), 8.48 (d, J=8.59 Hz, 1H), 8.23 (s, 1H), 7.69 (d, J=1.98 Hz, 1H), 7.44 (dd, J=8.64, 1.94 Hz, 1H), 3.78 (s, 3H), 2.75 (s, 3H).
Reaction SMILES: [NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:18]4[C:13](=[N:14][CH:15]=[C:16]([C:19]5[CH:38]=[CH:37][C:22]([CH2:23][N:24]6[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]6)=[CH:21][CH:20]=5)[CH:17]=4)[N:12]([S:39]([C:42]4[CH:48]=[CH:47][C:45]([CH3:46])=[CH:44][CH:43]=4)(=[O:41])=[O:40])[CH:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(O)(C(F)(F)F)=O>ClCCl>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:18]4[C:13](=[N:14][CH:15]=[C:16]([C:19]5[CH:20]=[CH:21][C:22]([CH2:23][N:24]6[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]6)=[CH:37][CH:38]=5)[CH:17]=4)[N:12]([S:39]([C:42]4[CH:43]=[CH:44][C:45]([CH3:46])=[CH:47][CH:48]=4)(=[O:41])=[O:40])[CH:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1
Reactant: Cc1ccc(S(=O)(=O)n2cc(-c3ccc4[nH]ccc4c3)c3cc(-c4ccc(CN5CCN(C(=O)OC(C)(C)C)CC5)cc4)cnc32)cc1
Solvent: O=C(O)C(F)(F)F
Solvent: ClCCl
Product: Cc1ccc(S(=O)(=O)n2cc(-c3ccc4[nH]ccc4c3)c3cc(-c4ccc(CN5CCNCC5)cc4)cnc32)cc1
Yield: 98.5 %

Procedure:
tert-butyl 4-(4-(3-(1H-indol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)benzyl)piperazine-1-carboxylate (500 mg) was suspended in 6 mL of dichloromethane and treated with TFA (5 mL) and reacted for 30 minutes. The solvent was removed in vacuo and the residue washed with 1 N sodium hydroxide solution, water and brine and dried over MgSO4 to yield 418 mg of crude product that was used without further purification (562 M+H).