Sodium Carbonate → HCID 59631296, compound

Participants

Reaction Conditions

Reaction Steps

A screw-cap vial was charged with 2,4-dichloro-5,7-difluoro-3-methylquinoline (600 mg, 2.42 mmol), 5-methylpyridine-3-boronic acid (348 mg, 2.54 mmol), dichlorobis(triphenylphosphine)palladium (II) (170 mg, 0.24 mmol), sodium carbonate (769 mg, 7.26 mmol), 1,4-dioxane (6.5 mL), and water (1.6 mL). The mixture was stirred at 95° C. for 22 h, then 0.2 additional equivalents of the aforementioned boronic acid were added and the reaction was continued for 18 h. Upon completion, the reaction was cooled to rt and partitioned between EtOAc and water. The organic layer was washed with brine, dried over magnesium sulfate, and cond. The resulting crude product was purified by flash chromatography (silica gel, 0-30% EtOAc in hexanes), affording 4-chloro-5,7-difluoro-3-methyl-2-(5-methylpyridin-3-yl)quinoline. Mass Spectrum (ESI) m/e=305.0 (M+1).

Provenance & Evidence