Tetrahydrofuran → Methyl 2-[3-(hydroxymethyl)imidazo[1,2-a]pyridin-2-yl]-1-naphthoate

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Reaction Steps

The compound prepared in Example 4 (195 mg) was added to tetrahydrofuran (1.5 mL) and suspended. A solution of sodium borohydride (34 mg) in water (0.4 mL) was added to the reaction mixture on ice bath, and the reaction mixture was stirred for an hour. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, and the reaction mixture was extracted twice with ethyl acetate. The obtained organic layer was joined, and washed with water, a saturated aqueous solution of sodium hydrogen carbonate and a saturated salt solution sequentially. The obtained organic layer concentrated under reduced pressure after drying with anhydrous sodium sulfate. The obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=25:75) to give the title compound (186 mg) having the following physical data.

Provenance & Evidence