Cesium carbonate → HCID 86653283, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 1-{[4-(2-chloropyridin-4-yl)piperazin-1-yl]methyl}-4-oxo-4H-quinolizine-3-carboxylate (0.500 g, 1.17 mmol), potassium vinyltrifluoroborate (0.471 g, 3.51 mmol), and 1N cesium carbonate (2.34 mL, 2.34 mmol) in 5 mL of THF under nitrogen was added bis(tri-tert-butyl-phosphine)palladium(0) (10 mol %). The reaction mixture was stirred at 130° C. for 5 hours, then cooled to room temperature. The mixture was diluted with EtOAc and washed with aqueous sodium bicarbonate and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 0-5% MeOH in DCM to provide ethyl 4-oxo-1-{[4-(2-vinylpyridin-4-yl)piperazine-1-yl]methyl}-4H-quinolizine-3-carboxylate that gave a mass ion (ES+) of 419.0 for M+H+.

Provenance & Evidence