4,5,6,7-Tetrahydro-2-methylthiazolo[5,4-c]pyridine → Potassium (2-methyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-5-yl)methyltrifluoroborate

Participants

Reaction Steps

A mixture of 2-methyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine (3.00 g), potassium bromomethyltrifluoroborate (3.91 g), KHCO3 (1.95 g), KI (0.32 g), and tetrahydrofuran (25 mL) is stirred at reflux temperature for 4 h. After cooling to room temperature, the solvent is evaporated and the residue is suspended in acetone. The insoluble salts are separated by filtration and the filtrate is treated with diethyl ether. The precipitate is separated by filtration and dried to give the title compound (alternatively, the crude product is purified by chromatography on silica gel using dichloromethane and methanol as eluent). Mass spectrum (ESI−): m/z=235 [M]−.

Provenance & Evidence