Cesium carbonate → 5-bromo-3-(2-(2,4-difluorophenoxy)-5-nitrophenyl)-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine

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Reaction Steps

A mixture of Example 182A (367 mg, 0.965 mmol), 2,4-difluorophenol (111 μl, 1.158 mmol) and cesium carbonate (472 mg, 1.448 mmol) in 8 mL DMSO was heated under nitrogen at 90° C. for 1.5 hours. The mixture was partitioned between water and ethyl acetate (80 mL). The aqueous phase was extracted with ethyl acetate (2×60 mL). The combined organics were washed with water (2×), saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel with a gradient of 10-70% ethyl acetate in heptanes to give the title compound (331 mg, 0.742 mmol, 77% yield) as a yellow solid.

Provenance & Evidence