Dimethylformamide → 6-Chloro-4-methoxypyridine-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 5-bromo-2-chloro-4-methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged with nitrogen for 15 min. At this point, Zn(CN)2 (3.96 g, 33.7 mmol) and Pd(Ph3P)4 (2.60 g, 2.25 mmol) were added, successively. The resulting suspension was stirred at 95° C. for 12 h under nitrogen atm. The reaction mixture was cooled to ambient temperature, filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue as an oil, which was purified on silica gel and eluted with 0-30% ethyl acetate/hexanes to afford the product. 1H NMR (500 MHz, DMSO-d6), δ 8.69 (s, 1H), 7.50 (s, 1H), 4.04 (s, 3H);

Provenance & Evidence