Ethanol → 2-(Benzofuran-2-carbonylamino)-4-(4-methyl-1-naphthyl)thiophene-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

Tert-butyl 2-(benzofuran-2-carbonylamino)-4-(trifluoromethylsulfonyloxy)thiophene-3-carboxylate (7), (4-methyl-1-naphthyl)boronic acid (46), tetrakis(triphenylphosphine)palladium(0), and sodium carbonate were combined in 2:1:1 ethanol, toluene and water the biphasic mixture was stirred vigorously in sealed vial at 70° C. After 2 hours, the mixture was filtered through Celite and the Celite rinsed with methylene chloride. The organic fraction of the filtrate was washed with water, dried with sodium sulfate, filtered, concentrated, purified by preparative layer chromatography (10% ethyl acetate/Hexane) then treated with a 1:1 mixture of methylene chloride and trifluoroacetic acid. After 4 hours the mixture was concentrated in vacuo, and the residue triturated in methylene chloride, centrifuged, decanted and dried under high vacuum to give 47A as a white powder (12.0 mg, 26%). 1H NMR (500 MHz, DMSO d6) δ=12.80 (br, 1 H), 12.60 (s, 1 H), 8.04 (d, 1 H), 7.88 (s, 1 H), 7.87 (d, 1 H), 7.74 (d, 1 H), 7.57-7.52 (m, 3 H), 7.46-740 (m, 2 H), 7.37 (d 1 H), 7.28 (d, 1 H), 7.04 (s, 1 H), 2.68 (s, 3 H) ppm. ESI MS [M+H] 428.21.

Provenance & Evidence