Cesium carbonate → 3-(3-Bromo-5-chlorophenoxy)-4-methylpyridine-2-carbonitrile

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Reaction Conditions

Reaction Steps

A mixture of 3-fluoro-4-methylpyridine-2-carbonitrile (11-1; 2.1 g, 15.43 mmol), 3-bromo-5-chlorophenol (3.68 g, 17.74 mmol) and cesium carbonate (5.03 g, 15.43 mmol) in DMF (30 mL) was heated to 70° C. for 1 hour and then to 80° C. for 1 hour. After this time, the reaction mixture was partitioned between water (300 mL) and ethyl acetate (2×500 mL). The combined extracts were washed with water (100 mL) and then brine (100 mL), dried over MgSO4, filtered and the solvent removed in vacuo. The residue was chromatographed using a RediSep column (330 g) and eluted with a gradient of 0-10% EtOAc/CH2Cl2 and the pure fractions combined and concentrated on the rotary evaporator to give the title compound. LRMS (M+1)=324.9.

Provenance & Evidence