Borane → 3-(Aminomethyl)-N-(3,5-dichlorobenzyl)-N-(4-fluorobenzyl)benzenesulfonamide
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:9]([N:12]([CH2:21][C:22]2[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=2)[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].B>C1COCC1>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([S:9]([N:12]([CH2:21][C:22]2[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=2)[CH2:13][C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-cyano-N-(3,5-dichlorobenzyl)-N-(4-fluorobenzyl)benzenesulfonamide (0.9 g, 2.00 mmol) in THF (10 mL) at rt was added dropwise a solution of borane (1 M solution in THF) (16 mL, 16.02 mmol) under nitrogen atmosphere. The reaction mixture was stirred at rt. for 3 h, acidified by dropwise addition of TEA and it was stirred for 30 min. The solvents were removed and the residue was diluted with ethyl acetate and saturated aq NaHCO3 solution. The organic layer was separated, washed with brine, dried over MgSO4, and the crude product was purified by flash silica gel column chromatography on silica gel (ISCO. Column: 24 g. Eluent: A: CH2Cl2. B: 10% of 2 M ammonia in MeOH of ethyl acetate. Condition: A to 40% of B (45 min gradient) to obtain the desired product as a white solid (0.29 g, 32%). 1H NMR (CDCl3): δ 7.82 (s, 1H), 7.75 (d, J=8.0 Hz, 1H), 7.63 (d, J=8.0 Hz, 1H), 7.54 (t, J=8.0 Hz, 1H), 7.20-7.19 (m, 1H), 7.11-7.08 (m, 2H), 6.97-6.92 (m, 2H), 6.86-6.85 (m, 2H), 4.32 (s, 2H), 4.26 (s, 2H), 4.00 (s, 2H), 1.58 (bs, 2H); MS (ESI): [M+H]+=452.9.