Methanol → Methyl 5-amino-2-[3-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)phenoxy]benzoate

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To a solution of methyl 2-[3-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)phenoxy]-5-nitrobenzoate (4.00 g, 8.70 mmol) in 1-methylpyrrolidin-2-one (20 mL)/methanol (40 mL)/tetrahydrofuran (10 mL) was added 10% palladium-carbon (400 mg), and the mixture was stirred at room temperature for 14 hr under a hydrogen atmosphere (1 atm). Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (200 mL), washed successively with water (100 mL×2) and saturated brine (100 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 to give the title compound (3.42 g, 92%) as a pale-yellow oil.

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