2-Chloronicotinonitrile → HCID 22180766, compound

Participants

Reaction Steps

To a degassed solution of 2-chloro-6-tributylstannylpyridine (prepared according to S. Choppin et al. in Org. Lett., 2000, 2, 803-5) (600 mg, 1.49 mmol) and 2-chloro-3-cyanopyridine (412 mg, 2.98 mmol) in THF was added tetrakis(triphenylphosphine)palladium(0) (60 mg, 0.05 mmol) and the mixture heated at reflux for 96 hours. The solvent was removed under reduced pressure and the crude product chromatographed on silica, on a gradient of dichloromethane to 2% methanol in dichloromethane, to afford 6′-chloro-2,2′-bipyridinyl-3-carbonitrile as a white solid (231 mg): δH (400 MHz, d6-DMSO) 7.71-7.74 (2H, m), 8.11 (1H, t, J 7.8), 8.20-8.23 (1H, m), 8.48 (1H, dd, J 1.8, 8.0), 8.97 (1H, dd, J 1.8, 4.9); m/z (ES+) 216, 218 (M++H).

Provenance & Evidence