Phosphorus oxychloride → 7-[(2,4-Dichloro-5-methoxyphenyl)amino]thieno[3,2-b]pyridine-6-carbonitrile

참여 물질

반응 조건

반응 단계

A suspension of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-(thien-3-ylamino)prop-2-enamide (500 mg, 1.35 mmol) in 35 mL of acetonitrile was heated to reflux and phosphorous oxychloride (0.84 mL, 8.98 mmol) was added dropwise. The mixture was heated at reflux overnight. The resultant solution was concentrated in vacuo and the residue was cooled to 0° C. Ice water was added followed by the slow addition of saturated aqueous sodium bicarbonate. The mixture was stirred for 10 minutes then partitioned between ethyl acetate and additional saturated aqueous sodium bicarbonate. The organic layer was washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was triturated with ethyl acetate and hexane to provide 337 mg (71%) of 7-[(2,4-dichloro-5-methoxyphenyl)amino]thieno[3,2-b]pyridine-6-carbonitrile, mp 208-210° C.; 1H NMR (400 MHz, DMSO-d6) δ 3.85 (s, 3H), 7.39 (s, 1H), 7.46 (d, J=5 Hz, 1H), 7.76 (s, 1H), 8.11 (d, J=5 Hz, 1H), 8.61 (s, 1H), 9.74 (s, 1H); MS (ES) m/z348.1, 350.0 (M−H)−

출처 및 근거