Dimethylcarbamoyl Chloride → 6-(3-Fluorophenyl)-5-methylpyridine-2-carbonitrile

Participants

Reaction Steps

A solution (40 mL) of 2-(3-fluorophenyl)-3-methylpyridine 1-oxide (4.26 g, 21.0 mmol), dimethylcarbamic acid chloride (2.94 g, 27.3 mmol) and trimethylsilanecarbonitrile (2.71 g, 27.3 mmol) in tetrahydrofuran was heated under reflux, and the mixture was stirred for 2 hr. After cooling to room temperature, the reaction solution was divided into two layers with ethyl acetate and saturated aqueous sodium hydrogen carbonate solution and subjected to extraction (3 times) with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography to give the title compound (4.42 g, 99%).

Provenance & Evidence