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

Participants

Reaction Conditions

Reaction Steps

3-Bromo-1H-pyrrolo[2,3-b]pyridine (7.5 g, 38.07 mmol) was dissolved in dry DMF (190 mL) and chilled to 0° C. Sodium hydride (60% dispersion in mineral oil, 2.13 g, 53.29 mmol) was then added, and the mixture stirred at 0° C. for 30 minutes. Benzenesulfonyl chloride (7.41 g, 41.87 mmol) was then added via syringe and the mixture stirred at 0° C. for 30 minutes. Another lot of benzenesulfonyl chloride (0.5 mL) was then added to consume the starting material. The reaction mixture was then carefully quenched with saturated ammonium chloride, followed by water (200 mL) to precipitate the product. The solids were collected by filtration and dried under vacuum 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), 8.19-8.23 (m, 2H), 7.79-7.84 (m, 2H), 7.57-7.62 (m, 1H), 7.47-7.53 (m, 2H), 7.25-7.29 (m, 1H).

Provenance & Evidence