反应详情

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.

1. additionacidified by dropwise addition of TEA and it
2. stirringwas stirred for 30 min
3. customThe solvents were removed
4. additionthe residue was diluted with ethyl acetate and saturated aq NaHCO3 solution
5. customThe organic layer was separated
6. washwashed with brine
7. dry with materialdried over MgSO4
8. customthe crude product was purified by flash silica gel column chromatography on silica gel (ISCO