Ethanol → ethyl 1-cyclopropyl-9-methyl-8-(1-methylisoindoline-5-yl)-4-oxo-4H-quinolizine-3-carboxylate

Participants

Reaction Steps

226.8 mg of ethyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (XIII) was suspended in 3 ml of toluene, and 1.6 ml of ethanol, 0.82 ml of a 2M sodium carbonate solution, 311.1 mg of (+)-1-methyl-2-tritylisoindoline-5-boric acid (3) and 23.2 mg of bis(triphenylphosphin)paradium (II) chloride were added thereto, and thereafter, under an argon atmosphere, the resulting mixture was heated under reflux for 4 hours. Ethyl acetate was added to the reaction solution and the organic layer was separated and rinsed with water, and thereafter, dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1) to obtain 335.9 mg of ethyl 1-cyclopropyl-9-methyl-8-(1-methylisoindoline-5-yl)-4-oxo-4H-quinolizine-3-carboxylate (XIV).

Provenance & Evidence