Methanol → N-{3-[(5-aminopyridin-2-yl)oxy]-4-methoxyphenyl}-3-(1-cyanocyclopropyl)benzamide

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To a solution of 3-(1-cyanocyclopropyl)-N-{4-methoxy-3-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide (4.30 g, 9.99 mmol) in tetrahydrofuran (100 mL) were added methanol (50 mL) and 10% palladium-carbon (982 mg), and the mixture was stirred at room temperature for 14 hr under a hydrogen atmosphere (2.5 atm). The insoluble material was filtered off, and the filtrate was concentrated to give the title compound (4.1 g) as a brown syrup substance. The syrup substance was used for the next reaction without further purification.

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