Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1)([O-:13])=[O:12].N1C=CC=CC=1>C(O)(=O)C>[N+:11]([C:14]1[CH:15]=[CH:16][C:17]([S:20]([NH:1][C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=2)[C:5]([NH2:7])=[O:6])(=[O:22])=[O:21])=[CH:18][CH:19]=1)([O-:13])=[O:12]
Reactant: O=[N+]([O-])c1ccc(S(=O)(=O)Cl)cc1
Reactant: NC(=O)c1cccc(N)c1
Solvent: CC(=O)O
Solvent: c1ccncc1
Product: NC(=O)c1cccc(NS(=O)(=O)c2ccc([N+](=O)[O-])cc2)c1
Temperature: 0 °C

Procedure:
A solution containing 44 g (0.32 m) of 3-aminobenzamide, 71.6 g (0.32 m) of p-nitrobenzenesulfonyl chloride and 700 ml of pyridine was stirred and heated on a steam bath for 2.5 hours, then poured into ice water. Acetic acid was added to a pH 5.0-6.0 and the resulting solid collected by filtration, washed with water and air-dried to give 105 g, m.p. 240°-244°.
Reaction SMILES: [Br:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[C:5](=[O:8])[NH:6][N:7]=1.N1C=CC=CC=1.[C:17]1([CH3:26])[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[C:5](=[O:8])[N:6]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH3:26])[N:7]=1
Reactant: Cn1c(=O)[nH]nc(Br)c1=O
Reactant: Cc1ccccc1B(O)O
Agent: [Cu+2]
Agent: CC(=O)[O-]
Solvent: ClCCl
Solvent: c1ccncc1
Product: Cc1ccccc1-n1nc(Br)c(=O)n(C)c1=O
Temperature: 25 °C
Reaction time: 24 h
Yield: 75 %

Procedure:
0.5 g (2.43 mmol) of intermediate 2a are placed in the presence of 0.4 mL (4.85 mmol) of pyridine, 0.66 g (4.85 mmol) of o-tolyl boronic acid, 0.66 g (3.64 mmol) of copper acetate in 50 mL of CH2Cl2. The reaction medium is stirred for 24 h at room temperature and then filtered on celite. The filtrate is washed with water, and then with 0.01N hydrochloric acid. After drying on MgSO4, the organic phase is dry concentrated. After washing the obtained residue with diethyl ether, 0.54 g of a white solid corresponding to the compound 41 are isolated (yield 75%)
Reaction SMILES: [Mg].[Cl:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11](Cl)[CH3:12].CON(C)[C:17]([C:19]1[CH:34]=[CH:33][C:22]2[N:23]([CH2:30][CH:31]=[CH2:32])[C:24](=[O:29])[N:25]([CH2:26][CH:27]=[CH2:28])[C:21]=2[CH:20]=1)=[O:18].O>C1COCC1>[CH2:30]([N:23]1[C:22]2[CH:33]=[CH:34][C:19]([C:17](=[O:18])[CH:11]([C:4]3[CH:5]=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=3[Cl:2])[CH3:12])=[CH:20][C:21]=2[N:25]([CH2:26][CH:27]=[CH2:28])[C:24]1=[O:29])[CH:31]=[CH2:32]
Reactant: COc1ccc(C(C)Cl)c(Cl)c1
Reactant: C=CCn1c(=O)n(CC=C)c2cc(C(=O)N(C)OC)ccc21
Agent: [Mg]
Solvent: C1CCOC1
Solvent: O
Product: C=CCn1c(=O)n(CC=C)c2cc(C(=O)C(C)c3ccc(OC)cc3Cl)ccc21
Temperature: -10 °C
Reaction time: 0.25 h
Yield: 52.8 %

Procedure:
A 1M suspension of Rieke magnesium in THF (1.3 ml) was added to THF (2 ml). The mixture was cooled to −10° C., and a solution of 2-chloro-1-(1-chloro-ethyl)-4-methoxy-benzene (136 mg) in THF (2 ml) was added. The mixture was stirred for 15 min. A solution of 1,3-diallyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methoxy-methyl-amide (100 mg) in THF (2 ml) was added at −10° C. The mixture was stirred overnight at room temperature. Water was added and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and then concentrated to an oil. The residue was purified by flash chromatography (SiO2, 0 to 100% EtOAc/heptane) to give the title compound (72 mg) as a light yellow foam. MS (m/e)=411.2 [M+H+].
Reaction SMILES: Cl[C:2]1[C:7]2[N:8]([CH2:20][C@H:21]3[CH2:26][CH2:25][C@H:24]([CH3:27])[CH2:23][CH2:22]3)[C:9]([N:11]3[CH2:16][CH2:15][O:14][C@@H:13]4[CH2:17][CH2:18][CH2:19][C@@H:12]34)=[N:10][C:6]=2[CH:5]=[C:4]([Cl:28])[N:3]=1.[Cl:29][C:30]1[CH:31]=[C:32](B2OC(C)(C)C(C)(C)O2)[C:33]([F:36])=[N:34][CH:35]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CCOC(C)=O>[Cl:28][C:4]1[N:3]=[C:2]([C:32]2[C:33]([F:36])=[N:34][CH:35]=[C:30]([Cl:29])[CH:31]=2)[C:7]2[N:8]([CH2:20][C@H:21]3[CH2:22][CH2:23][C@H:24]([CH3:27])[CH2:25][CH2:26]3)[C:9]([N:11]3[CH2:16][CH2:15][O:14][C@@H:13]4[CH2:17][CH2:18][CH2:19][C@@H:12]34)=[N:10][C:6]=2[CH:5]=1
Reactant: C[C@H]1CC[C@H](Cn2c(N3CCO[C@@H]4CCC[C@H]43)nc3cc(Cl)nc(Cl)c32)CC1
Reactant: CC1(C)OB(c2cc(Cl)cnc2F)OC1(C)C
Agent: O=C([O-])[O-]
Agent: [Cs+]
Solvent: O
Solvent: CCOC(C)=O
Product: C[C@H]1CC[C@H](Cn2c(N3CCO[C@@H]4CCC[C@H]43)nc3cc(Cl)nc(-c4cc(Cl)cnc4F)c32)CC1
Temperature: 90 °C

Procedure:
4,6-dichloro-2-[(trans)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine (racemic, 422 mg, 1 mmol), 5-chloro-2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (340 mg, 2 mmol) and Cs2CO3 (980 mg, 3 mmol) were added to degassed dioxane:water (10 mL:2 mL), followed by the addition of [1,1′-bis(di-tert-butylphosphino)ferrocene]PdCl2 (130 mg, 0.2 mmol). The reaction was heated at 90° C. for 24 hours. Water and EtOAc were added. The aqueous layer was extracted with EtOAc several times. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified on a silica gel column (0 to 60% EtOAc/hexanes) to afford 6-chloro-4-(5-chloro-2-fluoropyridin-3-yl)-2-[(trans)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine (racemic). MS ES calc'd. for C26H30Cl2FN5O [M+H]+ 518. found 518.
Reaction SMILES: [N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[C@@H:9]12[NH:16][C@@H:13]([CH2:14][CH2:15]1)[CH2:12][N:11]([C:17]1[CH:18]=[CH:19][C:20]3[N:21]([C:23]([C:26]([F:29])([F:28])[F:27])=[N:24][N:25]=3)[N:22]=1)[CH2:10]2>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:16]2[C@H:9]3[CH2:15][CH2:14][C@@H:13]2[CH2:12][N:11]([C:17]2[CH:18]=[CH:19][C:20]4[N:21]([C:23]([C:26]([F:29])([F:27])[F:28])=[N:24][N:25]=4)[N:22]=2)[CH2:10]3)[CH:2]=1
Reactant: FC(F)(F)c1nnc2ccc(N3C[C@H]4CC[C@@H](C3)N4)nn12
Reactant: O=Cc1cccnc1
Product: FC(F)(F)c1nnc2ccc(N3C[C@H]4CC[C@@H](C3)N4Cc3cccnc3)nn12
Yield: 68 %

Procedure:
A mixture of pyridine-3-carboxaldehyde and 6-[(1R,5S)-3,8-diazabicyclo[3.2.1]oct-3-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine was allowed to react by General Synthetic Method 5 to give 6-[(1R,5S)-8-(pyridin-3-ylmethyl)-3,8-diazabicyclo[3.2.1]oct-3-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine in 68% yield.