2-Chloro-4-cyanopyridine → 2-(1-Methylimidazol-4-yl)pyridine-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-4-pyridinenitrile (300 mg, 2.16 mmol) in toluene (10 mL) was added N-methyl-4-(tributylstannyl)imidazole (964 mg, 2.6 mmol), followed by tetrakistriphenylphosphine palladium (0) (150 mg, 0.13 mmol). The reaction mixture was heated at 120° C. in a microwave initiator for 1 hr. The mixture was cooled down to r.t, solid filtered and dried to give 250 mg of 2-(1-methyl-1H-imidazol-4-yl)pyridine-4-carbonitrile as a white solid. Filtrate was purified by flash column chromatography (CH2Cl2/MeOH=20/1) to give additional 100 mg of the product (total 350 mg, 88%). 1H NMR (400 MHz, DMSO-d6): δ 3.73 (3H, s), 7.59 (1H, d, J=4.8 Hz), 7.82 (1H, s), 8.09 (1H, s), 8.72 (1H, d, J=5 Hz). [M+H] Calc'd for C10H8N4, 185. Found, 185.

Provenance & Evidence