Cesium carbonate → N-[3-(4-amino-2-nitrophenoxy)phenyl]-3-(1-cyano-1-methylethyl)benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(1-cyano-1-methylethyl)-N-(3-hydroxyphenyl)benzamide (20 g, 71.3 mmol) produced in Example 1(i) and 4-fluoro-3-nitroaniline (10.9 g, 69.9 mmol) in N,N-dimethylformamide (150 mL) was added cesium carbonate (33.8 g, 104 mmol), and the mixture was stirred at 80° C. for 16 hr. The reaction mixture was cooled to room temperature, insoluble material was filtered off and washed with ethyl acetate. The filtrate and washings were combined and the mixture was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (300 mL), washed successively with water (300 ml) and saturated brine (150 mL×2), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (eluate: ethyl acetate), and the obtained solution was concentrated under reduced pressure. The residue was crystallized from ethyl acetate/n-hexane to give the title compound (23.8 g, 82%) as a red-orange powder.

Provenance & Evidence