Cesium fluoride → HCID 59631216, compound

Participants

Reaction Steps

A solution of 4-chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (2.67 g, 9.79 mmol), bis(tri-tert-butylphosphine)palladium (0) (0.600 g, 1.175 mmol), vinyl tributyl tin (3.26 mL, 10.28 mmol), cesium fluoride (1.49 g, 9.79 mmol), and dioxane (20 mL) was stirred at 105° C. under nitrogen for 30 minutes, then concd. The resulting residue was partitioned between EtOAc and water, and the organic phase was dried over magnesium sulfate and concd. This afforded a crude material that was purified by column chromatography (silica; 0-60% EtOAc in hexanes) to yield 7-fluoro-3-methyl-2-(pyridin-2-yl)-4-vinylquinoline as a white amorphous solid. Mass Spectrum (ESI) m/e=265.2 (M+1).

Provenance & Evidence