Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [Cl:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].C([N-]C(C)C)(C)C.[Li+].[CH3:18][N:19]([CH3:33])[S:20]([C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[C:25](F)[CH:24]=1)(=[O:22])=[O:21]>O1CCCC1>[Cl:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:25]1[CH:24]=[C:23]([S:20](=[O:22])(=[O:21])[N:19]([CH3:18])[CH3:33])[CH:31]=[CH:30][C:26]=1[C:27]([OH:29])=[O:28]
Reactant: CN(C)S(=O)(=O)c1ccc(C(=O)O)c(F)c1
Reactant: Nc1ccc(I)cc1Cl
Agent: CC(C)[N-]C(C)C
Agent: [Li+]
Solvent: C1CCOC1
Product: CN(C)S(=O)(=O)c1ccc(C(=O)O)c(Nc2ccc(I)cc2Cl)c1
Reaction time: 0.08 h

Procedure:
To a stirring cold (−78° C.) solution comprised of 2-chloro-4-iodoaniline (1 molar equivalent) in anhydrous tetrahydrofuran under a nitrogen atmosphere is added a commercially available lithium diisopropylamide solution (Aldrich, 2.0 M in tetrahydrofuran/heptane/ethylbenzene, 1 molar equivalent). After stirring for 5 minutes, a solution comprised of 4-dimethylsulfamoyl-2-fluoro-benzoic acid (1 molar equivalent) in tetrahydrofuran is added. The cold bath is removed and the reaction mixture is stirred for 2 hours. The reaction mixture is then partitioned between diethyl ether and dilute aqueous hydrochloric acid. The organic phase is washed with brine, dried over magnesium sulfate, and concentrated in vacuo to afford a product which may be purified by chromatography of recrystallization from an appropriate solvent like chloroform or heptane-ethanol.
Reaction SMILES: [CH2:1]([O:3][CH:4]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[CH3:17])[C:9]1=[O:18])[C:5]([OH:7])=O)[CH3:2].C([O-])(=O)C.[NH2:23][CH2:24][C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][C:26]=1[N+:33]([O-:35])=[O:34]>>[C:29]([C:28]1[CH:31]=[CH:32][C:25]([CH2:24][NH:23][C:5](=[O:7])[CH:4]([O:3][CH2:1][CH3:2])[N:8]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[CH3:17])[C:9]2=[O:18])=[C:26]([N+:33]([O-:35])=[O:34])[CH:27]=1)#[N:30]
Reactant: N#Cc1ccc(CN)c([N+](=O)[O-])c1
Reactant: CCOC(C(=O)O)N1Cc2c(C)cccc2C1=O
Agent: CC(=O)[O-]
Product: CCOC(C(=O)NCc1ccc(C#N)cc1[N+](=O)[O-])N1Cc2c(C)cccc2C1=O

Procedure:
According to general procedure C, (RS)-ethoxy-(4-methyl-1-oxo-1,3-dihydro-isoindol-2-yl)-acetic acid (intermediate of example 44) was coupled with 4-aminomethyl-3-nitrobenzonitrile (CAS 701269-65-0) to give (RS)-N-(4-cyano-2-nitro-benzyl)-2-ethoxy-2-(4-methyl-1-oxo-1,3-dihydro-isoindol-2-yl)-acetamide as off-white crystals, MS 409.4 ([M+H]+).
Reaction SMILES: [OH:1][CH:2]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[C:8]#[N:9])[CH2:3][CH3:4].CCN(CC)CC.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl>[CH3:20][S:21]([O:1][CH:2]([C:5]1[CH:12]=[CH:11][CH:10]=[C:7]([C:8]#[N:9])[CH:6]=1)[CH2:3][CH3:4])(=[O:23])=[O:22]
Reactant: CCC(O)c1cccc(C#N)c1
Reactant: CS(=O)(=O)Cl
Solvent: ClCCl
Solvent: CCN(CC)CC
Product: CCC(OS(C)(=O)=O)c1cccc(C#N)c1
Temperature: 25 °C
Reaction time: 1.5 h
Yield: 71.3 %

Procedure:
A mixture of 3-(1-hydroxypropyl)benzonitrile (0.273 g, 1.694 mmol; ref. Synlett (2002), (11), 1922-1924), Et3N (0.354 mL, 2.54 mmol) and MsCl (0.198 mL, 2.54 mmol) in CH2Cl2 (5 mL) was stirred at rt. After 90 min, an additional 0.75 eq each of Et3N and MsCl were added. After 1 h, the reaction mixture was concentrated to dryness, and the residue was partitioned between EtOAc (20 mL) and 0.1N HCl (20 mL). The organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was chromatographed over silica gel using a 5-30% EtOAc-hexane gradient to give 1-(3-cyanophenyl)propyl methanesulfonate (0.289 g, 68% yield) (the product is somewhat unstable, and it needs to be used shortly thereafter or stored at low temperatures).
Reaction SMILES: [CH3:1][O:2][CH2:3][CH2:4][C:5]([OH:7])=O.[F:8][C:9]1[C:37]([N:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)=[CH:36][C:12]2[N:13]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=3)[C:14]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:15][C:11]=2[CH:10]=1>ClCCl>[F:8][C:9]1[C:37]([N:38]2[CH2:39][CH2:40][N:41]([C:5](=[O:7])[CH2:4][CH2:3][O:2][CH3:1])[CH2:42][CH2:43]2)=[CH:36][C:12]2[N:13]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]([F:34])([F:35])[F:33])=[CH:27][CH:26]=3)[C:14]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:15][C:11]=2[CH:10]=1
Reactant: COCCC(=O)O
Reactant: Fc1cc2nc(COc3ccccc3)n(Cc3ccc(OC(F)(F)F)cc3)c2cc1N1CCNCC1
Solvent: ClCCl
Product: COCCC(=O)N1CCN(c2cc3c(cc2F)nc(COc2ccccc2)n3Cc2ccc(OC(F)(F)F)cc2)CC1

Procedure:
0.020 ml 3-methoxy-propionic acid (0.2 mmol) and 40 mg 1′1-carbonyldiimidazole (0.24 mmol) were refluxed in 4 ml dichloromethane under nitrogen for 40 minutes. 100 mg of 5-fluoro-2-phenoxymethyl-6-piperazin-1-yl-1-(4-trifluoromethoxy-benzyl)-1H-benzoimidazole (0.2 mmol) were added and the resulting mixture refluxed for additional 4.5 h. The reaction mixture was then diluted with dichloromethane, washed with water, saturated sodium bicarbonate and brine, dried with magnesium sulfate, filtered and concentrated in vacuo, leading to 129 mg yellow solid. This residue was purified by column chromatography (40 g silicagel, dichloromethane/methanol 24:1) leading to 44 mg off-white solid (37%). MS (ISP) 587.2 (M+H)+.