Thieno(2,3-c)pyridine → HCID 10740978, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence