反应详情

温度

-78 °C

To a cold (−78° C.) solution of thieno[2,3-c]pyridine (524 mg, 3.88 mmol) in anhydrous THF (50 mL) was added n-butyllithium (2.66 mL, 4.26 mmol) dropwise. The mixture was stirred for 60 minutes at −78° C. A solution of tributylchlorostannane (1.254 mL, 4.65 mmol) in anhydrous THF (10 mL) was added, and the reaction mixture was stirred for 30 minutes at −78° C. The solution was allowed to warm to room temperature over a period of 2 to 3 hours. Saturated aqueous sodium bicarbonate was added. The aqueous phase was extracted with diethyl ether (3×200 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo. The crude product was purified by silica gel column chromatography, eluting with a gradient of 10-50% EtOAc and hexane over a period of 60 minutes. The desired fractions were collected to give the title compound as a clear oil (1.1 g, 67%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.86 (t, J=7.32 Hz, 9H), 1.08-1.38 (m, 12H), 1.45-1.71 (m, 6H), 7.59 (s, 1H), 7.76-7.93 (m, 1H), 8.41 (s, 1H), 9.23 (s, 1H).

1. stirringthe reaction mixture was stirred for 30 minutes at −78° C
2. temperatureto warm to room temperature over a period of 2 to 3 hours
3. extractionThe aqueous phase was extracted with diethyl ether (3×200 mL)
4. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
5. filtrationfiltered
6. customevaporated in vacuo
7. customThe crude product was purified by silica gel column chromatography
8. washeluting with a gradient of 10-50% EtOAc and hexane over a period of 60 minutes
9. customThe desired fractions were collected