HCID 59398526, compound → 4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)aniline

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Reaction Conditions

Reaction Steps

4-(1-Benzyloxymethyl-1H-pyrrolo[2,3-b]pyridin-4-yloxy)aniline (21.3 g, 61.7 mmol) was dissolved in methanol (300 mL) and 10 N hydrochloric acid (20 mL), and palladium carbon (10%, 800 mg) was added thereto. The resulting mixture was stirred under a hydrogen atmosphere at 50° C. for 7 hours. The catalyst was removed by celite filtration, and the resulting methanol solution was concentrated. The residue was added to THF (500 mL) and a 5 N sodium hydroxide aqueous solution (100 mL), and the resulting mixture was stirred. The solid was immediately dissolved, and the reaction solution was separated into two layers. The solution was subsequently stirred at room temperature for 3 hours, and saturated brine (300 mL) was added thereto. The THF layer was isolated and washed with saturated brine (100 mL). The organic layer was dried over anhydrous sodium sulfate and then concentrated. The residue was purified by amino-silica gel (Fuji Silysia, 1 L of ethyl acetate) to give 4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)aniline (10.46 g, yield: 75%).

Provenance & Evidence