Benzenesulfonyl chloride → 4-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

Participants

Reaction Steps

To a solution of 4-bromo-1H-pyrrolo[2,3-b]pyridine (15 g, 76 mmol) in N,N-dimethyformamide (300 mL) was added NaH (95%, 3.96 g, 99 mmol) at 0° C. The mixture was allowed to warm up to room temperature and was stirred for another 30 minutes. Benzenesulfonyl chloride (11.78 mL, 91 mmol) was added. After stirring at room temperature for 16 hours, the reaction mixture was quenched with aqueous NaHCO3 solution and was extracted with ethyl acetate (three times with 450 mL). The combined organic layers were washed with water, dried over MgSO4, and filtered. The filtrate was concentrated and the residue was separated by flash chromatography on silica gel (Teledyne CombiFlash Rf, 5% of ethyl acetate in dichloromethane) to provide the title compound. MS (ESI+) m/z 337 (M+1).

Provenance & Evidence