Acetonitrile → 2-Acetylamino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

Participants

Reaction Steps

To a mixture of 2-amino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide described in Example A-67 (50 mg, 0.15 mmol), acetonitrile (5 mL) and tetrahydrofuran (2 mL) was added nitronium tetrafluoroborate (0.50M sulfolane solution, 0.46 mL, 0.23 mmol) on an ice bath, and the solution was stirred overnight at room temperature. Water, ethyl acetate, tetrahydrofuran and an aqueous solution of saturated sodium bicarbonate were added to the reaction solution for extraction, washed with brine, then, the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (methanol:ethyl acetate=1:30), and the title compound (1.3 mg, 0.0035 mmol, 2.3%) was obtained as a white solid.

Provenance & Evidence