Ammonium Chloride → HCID 86762434, compound

Participants

Reaction Conditions

Reaction Steps

Under an atmosphere of argon, 5-bromo-2,3-difluoropyridine (5 g, 25.8 mmol, Eq: 1.00) and cyclopropanecarbonitrile (1.78 g, 2.00 ml, 25.8 mmol, Eq: 1.00) were combined with toluene (50.0 ml) to give a colorless solution. The reaction mixture was cooled to −5° C. Potassium bis(trimethylsilyl)amide (0.5 M, 51.6 ml, 25.8 mmol, Eq: 1.00) was added dropwise at −5° C. The reaction mixture was stirred 1 hr at −5° C., and over the weekend at RT. The reaction mixture was then poured into NH4Cl solution (satd., 50 ml). The aqueous layer was extracted with ethyl acetate (3×60 ml). The organic layers were combined and dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 70 g, 0% to 50% ethyl acetate in heptane as eluent) to yield the title compound as a light brown waxy solid (0.49 g, 7.89%, MS (m/e)=248.1 [M+H+]).

Provenance & Evidence