Ethyl bromoacetate → ethyl 2-(2-cyano-3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate

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Reaction Conditions

Reaction Steps

To a mixture of 3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole-2-carbonitrile (29.1 mg, 0.085 mmol), cesium carbonate (110 mg, 0.339 mmol), and TBAI (3.13 mg, 8.47 μmol) in DMF (424 μl), was added ethyl bromoacetate (14.15 μl, 0.127 mmol). The mixture was heated at 60° C. for 5 hours and then allowed to cool down to room temperature and diluted with ethyl acetate (100 ml). The resulting mixture was washed with water (50 ml×3), dried, filtered, and evaporated to give an oil. This crude oil was purified by column chromatography (0 to 50% ethyl acetate in hexanes) to give ethyl 2-(2-cyano-3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (40.0 mg, 0.093 mmol, 110% yield).

Provenance & Evidence