Benzenesulfonyl chloride → 3-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (2.13 g, 53.3 mmol, 60% dispersion in mineral oil) was added to 3-bromo-1H-pyrrolo[2,3-b]pyridine (7.5 g, 38.1 mmol) in DMF (190 mL) at 0° C. This mixture was stirred at 0° C. for 30 minutes, and benzene sulfonyl chloride (7.40 g, 41.87 mmol) was then added by syringe. After 30 minutes at 0° C., TLC indicated most of the starting material had been consumed. Benzene sulfonyl chloride (0.5 mL) was added, and the mixture was stirred for another 15 minutes at 0° C. The mixture was then quenched with saturated ammonium chloride solution (100 mL) followed by water (200 mL). A precipitate had formed. The solids were collected by filtration and dried under high vacuum for 16 hours to give 3-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (11.2 g, 87%) as a solid. 1H NMR (400 MHz, CDCl3) δ 8.46-8.49 (m, 1H), 8.19-8.22 (m, 2H), 7.79-7.83 (m, 2H), 7.57-7.62 (m, 1H), 7.47-7.53 (m, 2H), 7.25-7.29 (m, 1H).

Provenance & Evidence