Cesium carbonate → Ethyl 5-(3-chloro-5-fluorophenyl)-4-(3-cyano-4-fluorophenyl)thiophene-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

Under argon, 220 mg (0.61 mmol) of the compound from Example 9A are provided in 6.2 ml of 1,2-dimethoxyethane, and 100 mg (0.61 mmol) of 3-cyano-4-fluorophenylboronic acid, 593 mg (1.82 mmol) of cesium carbonate, 20.0 mg (0.04 mmol) of dicyclohexyl[2′,4′,6′-tri(propan-2-yl)biphenyl-2-yl]phosphane and 4.0 mg (0.02 mmol) of palladium(II) acetate are added. The mixture is stirred at 50° C. overnight. The same amount of catalyst and ligand is added once more, and the mixture is stirred at 50° C. overnight. The reaction mixture is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient with addition of 0.1% formic acid). 86.0 mg (35% of theory) of the title compound are obtained.

Provenance & Evidence