Dichloromethane → HCID 86593499, compound

Participants

Reaction Steps

To a solution of 7-chlorothieno[3,2-b]pyridine-6-carbonitrile (100 mg, 0.45 mmol) in 5 mL of dichloromethane is added, in portions, (tert-butoxycarbonylmethylene)triphenylphosphorane (0.645 mL, 1.29 mmol). After stirring for 2.5 hours, the reaction mixture is allowed to stand at room temperature overnight. The mixture is concentrated to ½ its volume and is purified by flash column chromatography eluting with dichloromethane to provide 126 mg of tert-butyl (2E)-3-(7-chloro-6-cyanothieno[3,2-b]pyridin-2-yl)prop-2-enoate as a white solid, mp 193–194° C.; 1H NMR (CDCl3) δ 1.55 (s, 9H), 6.46 (d, J=16 Hz, 1H), 7.26 (s, 1H), 7.70 (s, 1H), 7.77 (d, J=16 Hz, 1H), 8.84 (s, 1H); MS 321.1, 323.2 (M+H)+

Provenance & Evidence