Benzenesulfonyl chloride → 1-(Benzenesulfonyl)-4-chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Steps

To a solution of 4-chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine (Adesis, 4.60 g, 27.0 mmol) in N,N-dimethylformamide (70 mL) was added 60% sodium hydride in mineral oil (1.186 g, 29.7 mmol) at 0° C. and the mixture was warmed to room temperature and stirred for 30 minutes. Benzenesulfonyl chloride (3.79 mL, 29.7 mmol) was added and after stirring 3 hours, the mixture was quenched with water and aqueous sodium bicarbonate. The suspension was filtered, washed with aqueous sodium bicarbonate, water, and heptanes, and vacuum oven-dried to give the title compound. MS (ESI+) m/z 311.0 (M+H)+.

Provenance & Evidence