Benzenesulfonyl chloride → 7-bromo-7-(phenylsulfonyl)-5H-pyrrolo[3,2-b]pyrazine

Participants

Reaction Conditions

Reaction Steps

A solution of 7-bromo-5H-pyrrolo[3,2-b]pyrazine (1 g, 5.05 mmol) in N,N-dimethylformamide (10 ml) was cooled at 0° C., and sodium hydride (167 mg, 5.55 mmol) was added in several portions. After stirring at 0° C. for 30 minutes, benzenesulfonyl chloride (980 mg, 5.55 mmol) was added via syringe. The mixture was allowed to warm up to room temperature and stirred for 4 hours. The reaction mixture was partitioned between ethyl acetate and brine. The organic phase was washed with brine and concentrated. The residue was purified by flash chromatography (30% ethyl acetate in hexane) to afford the title compound. MS (DCI/NH3) m/z 339 (M+H)+.

Provenance & Evidence