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

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Reaction Steps

To a 0° C. solution of Example 1a (25 g, 127 mmol) in N,N-dimethylformamide (200 mL) was slowly added sodium hydride (3.37 g, 133 mmol) over several minutes. After stirring for 30 minutes in the cold water bath, benzenesulfonyl chloride (17.18 ml, 133 mmol) was added via a syringe. The solution was allowed to warm to room temperature overnight, quenched slowly with 500 mL water, stirred for 30 minutes, and then filtered. The solid obtained was washed with water, followed by 300 mL of hexanes, dried over high-vacuum for 16 hours to give 34 g of the title compound which was used without further purification. MS (ESI+) m/z 338.7 (M+H)+.

Provenance & Evidence