Cesium carbonate → Methyl 6-(2-fluorophenyl)-5'-methyl-3,3'-bipyridine-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 6-chloro-5′-methyl-3,3′-bipyridine-5-carboxylate (3-2, 4.25 g, 16.16 mmol) in degassed dimethylformamide (81 mL) at 25° C. was added 2-fluorophenylboronic acid (2.94 g, 21.01 mmol), PdCl2dppf (1.18 g, 1.62 mmol) and 4M aqueous cesium carbonate (10.1 mL, 40.4 mmol). The reaction flask was purged with nitrogen, sealed and stirred for 4 hours at 40° C. The crude reaction mixture was partitioned between water and EtOAc, separating layers and washing the organic layer with saturated sodium bicarbonate solution and brine. The solvent was removed by rotary evaporation and the crude product was taken up in DCM (40 mL). Quadrapure TU (6 g) was added and the mixture was stirred overnight at room temperature. Filtration and concentration afforded the title compound (3-3) as a solid. ESI+MS [M+H]+ C19H15FN2O2=323.1.

Provenance & Evidence