Cesium carbonate → HCID 86645056, compound

Participants

Reaction Conditions

Reaction Steps

In a 2-5 mL Emrys™ process vial, the ethyl 1-{[4-(3-bromopyridin-2-yl)-4-cyanopiperidin-1-yl]methyl}-4-oxo-4H-quinolizine-3-carboxylate (50 mg, 0.10 mmol) was dissolved in 0.40 mL of anhydrous THF and treated with potassium vinyltrifluoroborate (40.6 mg, 0.30 mmol) and 1M cesium carbonate solution (0.20 mL, 0.20 mmol). The reaction was purged with a stream of nitrogen, charged with bis(tri-tert-butylphosphine)palladium(0) (5.2 mg, 0.010 mmol), and heated via Emrys Optimizer™ microwave to 160° C. for 10 minutes. Filtration and solvent removal provided material, which was subjected to preparative reverse phase HPLC. Collection of product containing fractions and removal of solvent afforded the ethyl 1-{[4-cyano-4-(3-vinylpyridin-2-yl)piperidin-1-yl]methyl}-4-oxo-4H-quinolizine-3-carboxylate.

Provenance & Evidence