Dimethylformamide → 3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole-2-carbonitrile

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Reaction Conditions

Reaction Steps

A mixture of 2,4-dimethyl-3-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole (128.0 mg, 0.402 mmol) and N-chlorosulfonylisocyanide (43.7 μl, 0.502 mmol) in acetonitrile (2.0 ml) was stirred at 25° C. for 1 hour. DMF (31.1 μl, 0.402 mmol) was then added and the resulting mixture was stirred for an additional 16 h at room temperature. The reaction was quenched with water (100 ml) and extracted with dichloromethane (100 ml×2). The organic layers were combined, filtered, and evaporated to give an oil. The oil was purified by column chromatography (0 to 50% ethyl acetate in hexanes) to give 3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole-2-carbonitrile (49.6 mg, 0.144 mmol, 35.9% yield).

Provenance & Evidence