Potassium Carbonate → N-{4-chloro-2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}-3-(1-cyano-1-methylethyl)benzamide

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Reaction Conditions

Reaction Steps

To a solution of 2-chloro-5-nitropyridine (952 mg, 6.01 mmol) and N-(4-chloro-2-fluoro-5-hydroxyphenyl)-3-(1-cyano-1-methylethyl)benzamide (2.00 g, 6.01 mmol) in N,N-dimethylformamide (20 mL) was added potassium carbonate (1.24 g, 9.01 mmol), and the mixture was stirred at 80° C. for 16 hr. The reaction mixture was cooled to room temperature, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. Water (100 mL) was added to the obtained residue, and the mixture was extracted with ethyl acetate (200 mL and 100 mL). The combined organic layer was washed with 5% aqueous sodium hydrogen carbonate solution (200 mL) and saturated brine (200 mL×2), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by basic silica gel column chromatography (ethyl acetate). The obtained solution was concentrated under reduced pressure to give the title compound (2.28 g, 83%) as a yellow oil.

Provenance & Evidence