Cesium carbonate → 6-(3-Chlorophenyl)-5-(tetrahydrofuran-2-yl)-pyridine-2-carboxylic acid methyl ester

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Reaction Steps

A solution of 6-bromo-5-(tetrahydrofuran-2-yl)-pyridine-2-carboxylic acid methyl ester (mixture of example 101d, 0.296 g, 1 mmol), 3-chlorophenylboronic acid (CAN 63503-60-6, 0.24 g, 1.5 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride methylene chloride complex (CAN 95464-05-4, 34 mg) and cesium carbonate (CAN 534-17-8, 1 g, 3 mmol) in DMF (10 mL) was stirred overnight at 80° C. under a nitrogen atmosphere. After filtration, the reaction mixture was poured into 20 mL H2O and washed with ethyl acetate (2×20 mL). The organic layer was concentrated under reduced pressure to provide the title compound (0.3 g, 91%) as black oil which was used in the next step without further purification; MS (EI): m/e=318.1 [M+H]+.

Provenance & Evidence