Cesium carbonate → Ethyl 4-bromo-5-(3-cyanophenyl)furan-2-carboxylate

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Reaction Steps

Under argon, 3.00 g (10.1 mmol) of the compound from Example 2A are provided in 96 ml of 1,2-dimethoxyethane, and 1.63 g (11.1 mmol) of 3-cyanophenylboronic acid, 9.84 g (30.2 mmol) of cesium carbonate, 0.14 g (0.30 mmol) of dicyclohexyl[2′,4′,6′-tri(propan-2-yl)biphenyl-2-yl]phosphane and 0.16 g (0.71 mmol) of palladium(II) acetate are added. The mixture is stirred at RT overnight. 0.44 g (3.02 mmol) of 3-cyanophenylboronic acid are subsequently added, and the mixture is stirred at RT for a further 24 h. The mixture is concentrated and the crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 20:1). 1.15 g (36% of theory) of the title compound are obtained.

Provenance & Evidence