Methyl 5-bromopyridine-3-carboxylate → Methyl 5-cyanopyridine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

CuCN (5.22 g, 58.3 mmol) was added to a solution of methyl 5-bromonicotinate (6 g, 27.8 mmol) in dry DMF (150 mL). The solution was purged with argon and heated to 160° C. for 12 h under argon atmosphere. The reaction mixture was cooled to room temperature and then quenched with saturated NH4Cl solution. Further EtOAc was added and the reaction mixture was stirred for 10 min. The reaction mixture was filtered through a Celite plug, the organic layer was separated, washed with water and brine, and dried over anhydrous Na2SO4. Solvent was evaporated under reduced pressure to get methyl-5-cyano-nicotinate as greenish-white solid (2.7 g, yield 60%): 1H NMR (300 MHz, DMSO-d6) δ 9.29-9.27 (m, 2H), 8.77 (s, 1H), 3.91 (s, 3H)

Provenance & Evidence