Ethanol → HCID 71185764, compound

Participants

Reaction Conditions

Reaction Steps

(4-methoxyphenyl)boronic acid (0.56 g, 3.70 mmol) and potassium carbonate (1.40 g, 10.11 mmol) were added to a solution of methyl 5-bromo-3,4-dimethylthiophene-2-carboxylate (9b, 0.8 g, 3.37 mmol) in a mixture of toluene:ethanol (10:30 ml) in a tube at 25° C. Nitrogen gas was bubbled through reaction mixture for 15 minutes. Tetrakis(triphenylphosphine)(0)palladium (0.19 g, 0.17 mmol) was added to the reaction mixture under nitrogen and the tube was sealed. The reaction mixture was heated at 95-100° C. for 2 hr under stirring. The progress of the reaction was monitored by TLC. The reaction mixture was then cooled to 25° C. and was filtered through celite. The celite cake was washed with ethyl acetate (30 ml). The combined filtrate was concentrated under reduced pressure to obtain a crude product. The resulting crude product was further purified by column chromatography using 5% ethyl acetate in hexanes as an eluent to obtain the title compound 9c (0.84 g, 90%).

Provenance & Evidence