Benzaldehyde → N-benzyl-6-bromo-5-chloropyridin-2-amine

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Reaction Steps

A solution of Example 11A (500 mg, 2.410 mmol) in 1,2-dichloroethane (10 mL) and acetic acid (5 mL) was treated with benzaldehyde (281 mg, 2.65 mmol) and the mixture was stirred at room temperature for 2 hours. Sodium triacetoxyborohydride (2.043 g, 9.64 mmol) was added and the mixture was stirred at room temperature for 12 hours. The mixture was diluted with water (25 mL), treated with saturated sodium bicarbonate solution, extracted with ethyl acetate, and washed with water and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated to afford the crude title compound. Purification by column chromatography (silica gel, 15% ethyl acetate in hexane) afforded the title compound.

Provenance & Evidence