4-Aminophenol → 4-(1-benzyloxymethyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)aniline

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Reaction Steps

P-Aminophenol (800 mg, 7.33 mmol) and potassium t-butoxide (820 mg, 7.31 mmol) were dissolved in NMP (10 mL), and potassium carbonate (510 mg, 3.69 mmol) was added thereto. The resulting mixture was stirred at room temperature for 1 hour, and 1-benzyloxymethyl-4-chloro-1H-pyrazolo[3,4-b]pyridine (860 mg, 5.62 mmol) was added thereto. The resulting mixture was stirred at 80° C. for 0.5 hours. The reaction container was cooled, and the content was diluted with water (100 mL) and extracted with ethyl acetate (100 mL) three times. The combined organic layer was washed with saturated brine (50 mL) twice, dried, and concentrated. The residue was purified by silica-gel column chromatography (Fuji Silysia, BW300, 30 g, n-hexane:EtOAc=1:1) to give 4-(1-benzyloxymethyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)aniline as a light-yellow syrup (1105 mg, yield: quantitative).

Provenance & Evidence