Water → 1H-Pyrrolo[2,3-b]pyridine, 3-iodo-5-methoxy-1-(phenylsulfonyl)-

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Reaction Steps

To a solution of 3-iodo-5-methoxy-1H-pyrrolo[2,3-b]pyridine (15, 4.30 g, 15.7 mmol) in 53.6 mL of N,N-dimethylformamide under nitrogen, sodium hydride (0.690 g, 60% in mineral oil, 17.2 mmol) was added. After 10 minutes, benzenesulfonyl chloride (11, 2.20 mL, 17.2 mmol) was added and the reaction was cooled in a water bath. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate purified by silica gel column chromatography, eluting with 30-100% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (16, 4.60 g).

Provenance & Evidence