3-Methylenecyclobutanecarbonitrile → 1-(3-Fluoropyridin-2-yl)-3-methylenecyclobutane-1-carbonitrile

Participants

Reaction Steps

To a solution of 3-methylenecyclobutanecarbonitrile (150 g, 1.61 mol, 1 equiv) and 2-chloro-3-fluoropyridine (212 g, 1.61 mmol, 1 equiv) in toluene (1 L) was added NaHMDS (2 M in THF, 885 mL, 1.1 equiv) dropwise at 0-10° C. Upon completion of addition, the reaction mixture was warmed to rt, stirred overnight, and quenched with NH4C(sat.) solution. The organic layer was washed with water (500 mL×2) and brine (500 mL), dried over Na2SO4, filtered, and concentrated to give a crude title compound (272 g, 90%), which was used in the next step without further purification, LRMS (M+H+) m/z 189.1.

Provenance & Evidence