反应详情

A mixture of methyl 4-(5-cyano-4-oxo-4,7-dihydrothieno[2,3-b]pyridin-2-yl)butanoate (136 mg) and 2 drops of N,N-dimethylformamide in 5 mL of phosphorous oxychloride is heated at reflux for 10 minutes and concentrated. To the residue is added dichloromethane and the solution is washed with 1% aqueous sodium bicarbonate solution. The organic layer is dried and concentrated. The residue is purified by flash column chromatography eluting with dichloromethane to provide 126 mg of 4-(4-chloro-5-cyano-thieno[2,3-b]pyridin-2-yl)-butyric acid methyl ester as a tan solid, mp 55–57° C.; 1H NMR (DMSO-d6) δ 1.98 (quintet, J=7 Hz, 2H), 2.42 (t, J=7 Hz, 2H), 3.04 (t, J=7 Hz, 2H), 3.59 (s, 3H), 7.42 (s, 1H), 8.94 (s, 1H); MS 295.1 (M+H)+

1. temperatureis heated
2. temperatureat reflux for 10 minutes
3. concentrationconcentrated
4. additionTo the residue is added dichloromethane
5. washthe solution is washed with 1% aqueous sodium bicarbonate solution
6. customThe organic layer is dried
7. concentrationconcentrated
8. customThe residue is purified by flash column chromatography
9. washeluting with dichloromethane