反应详情

温度

0 °C

Sodium hydride (4.1 g, 60% dispersion in mineral oil, 101 mmol) was added portionwise to a cooled (0° C.) solution of 1-benzenesulfonyl-5-chloro-2-bromomethyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester (40.8 g, 91.9 mmol) and N-cyanomethyl-4-methyl-benzenesulfonamide (21.3 g, 101 mmol) in DMF (400 mL). The reaction mixture was stirred at 0° C. for 15 minutes, then allowed to warm to ambient temperature and stirred for 1 hour. The reaction mixture was poured into a cooled, stirred solution of 2M hydrochloric acid (400 mL). The resultant precipitate was collected by filtration (slow) and the cake washed with water, followed by methanol and then diethyl ether. The resulting cake was dried to afford the title compound as a tan solid (39.6 g, 75%). LCMS (Method B: RT=4.58 min, M+H+=573/575. 1H NMR (400 MHz, CDCl3): 8.40 (d, J=2.4 Hz, 1H), 8.33-8.33 (m, 2H), 8.27 (d, J=2.4 Hz, 1H), 7.78 (d, J=8.2 Hz, 2H), 7.64-7.64 (m, 1H), 7.55-7.54 (m, 2H), 7.34 (d, J=8.1 Hz, 2H), 5.43 (s, 2H), 4.28 (s, 2H), 3.96 (s, 3H), 2.43 (s, 3H).

1. temperatureto warm to ambient temperature
2. stirringstirred for 1 hour
3. additionThe reaction mixture was poured into a cooled
4. filtrationThe resultant precipitate was collected by filtration (slow)
5. washthe cake washed with water
6. customThe resulting cake was dried