Sodium Carbonate → 7-Benzyloxy-8-bromomethyl-2-methoxy-[1,5]naphthyridine

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Reaction Steps

Phosphorus tribromide (32 μL, 0.34 mmol, 2.0 eq) is added at room temperature to a stirred solution of (3-benzyloxy-6-methoxy-[1,5]naphthyridine-4-yl)-methanol (50 mg, 0.17 mmol, 1.0 eq) in dichloromethane (5 mL). After 1 hour stirring at room temperature, pH of the reaction mixture is adjusted to 7 by the addition of a sodium carbonate aqueous solution. The resulting solution is extracted with dichloromethane (3×10 mL) and water (10 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford 7-benzyloxy-8-bromomethyl-2-methoxy-[1,5]naphthyridine as a white solid (62 mg, 99% yield).

Provenance & Evidence