Cyclopropanecarbonitrile → 1-(5-Fluoropyridin-2-yl)cyclopropane-1-carbonitrile

Participants

Reaction Steps

Cyclopropanecarbonitrile (815 mg) was dissolved in THF (15 ml) and the solution cooled to 0° C. before dropwise addition of 0.9 M KHMDS (14.0 ml). The reaction mixture was allowed to warm to room temperature and stirred for further 15 min. The resulting solution was then added dropwise to a solution of 2,5-difluoropyridine (1.52 g) in THF (15 ml) and the reaction mixture stirred for 1 hour. Reaction was quenched by addition of aqueous NH4Cl, stirred for 5 min and then the organics washed with NaHCO3 and brine and dried over Na2SO4. The mixture was then concentrated in vacuo and the residue was purified by flash column chromatography (SiO2; gradient: heptane/EtOAc) to give title compound as a white solid (880 mg). MS (ISP): 163.2 ([M+H]+)

Provenance & Evidence