Acetic Acid → methyl 5-bromo-2-methyl-3-((tetrahydro-2H-pyran-4-yl)amino)benzoate

Participants

Reaction Steps

To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (15 g, 61 mmol) and dihydro-2H-pyran-4(3H)-one (9.2 g, 92 mmol) in dichloroethane (300 mL), acetic acid (22 g, 368.4 mmol) was added and the reaction stirred at room temperature for 2 h. Then sodium triacetoxyborohydride (39 g, 184 mmol) was added at 0° C. and the reaction stirred overnight at room temperature. The solvent was removed under reduced pressure and the crude material was purified by column chromatography to afford the title compound (14 g, 69%).

Provenance & Evidence