N-{4-chloro-2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}-2,2,2-trifluoroacetamide → N-{5-[(5-aminopyridin-2-yl)oxy]-4-chloro-2-fluorophenyl}-2,2,2-trifluoroacetamide

Participants

Reaction Conditions

Reaction Steps

A mixture of N-{4-chloro-2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}-2,2,2-trifluoroacetamide (600 mg, 1.58 mmol), reduced iron (452 mg, 8.09 mmol) and acetic acid (10 mL) was stirred at 60° C. for 1.5 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (20 mL), washed with saturated aqueous sodium hydrogen carbonate solution (10 mL) and saturated brine (10 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→34/66) to give the title compound (357 mg, 65%) as a white powder.

Provenance & Evidence