Benzyl Alcohol → 3-(Benzyloxy)-7-bromo-1,5-naphthyridine

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To a solution of benzyl alcohol (2.25 g, 20.8 mmol) in DMF (25 mL) was added NaH (60% in mineral oil, 0.83 g, 20.8 mmol). The resulting mixture was heated to 60° C. for 10 minutes and was added to 3,7-dibromo-1,5-naphthyridine (Intermediate 3, 5.0 g, 17.4 mmol) in DMF (25.0 mL) at 100° C. The resulting mixture was stirred over night at 100° C., cooled, and concentrated under reduced pressure. Water (50 mL) was added and the aqueous layer was washed with DCM (3×50 mL). The organic layers were combined, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification (FCC, SiO2, DCM/petroleum ether, 1:1) afforded the title compound as a white solid (2.0 g, 36.7%).

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