Acetic Acid → 3-(Azidomethyl)-N-(4-chlorobenzyl)-2-(hydroxymethyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Participants

Reaction Steps

To a cold (0° C.), stirred solution of 230 mg of 3-(azidomethyl)-N-(4-chlorobenzyl)-2-formyl-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide in 6 mL of CH2Cl2 is added 0.16 mL of acetic acid and 296 mg of sodium triacetoxyborohydride. The ice bath is removed and the solution allowed to stir at room temperature for 2 h. Aqueous workup (CHCl3/aq. NaHCO3) followed by flash chromatography on silica using 3% MeOH in CH2Cl2 affords 150 mg of the title compound as a white solid. Recrystallization from acetonitrile provides off-white crystals.

Provenance & Evidence