Piperidine → HCID 66785466, compound

Participants

Reaction Conditions

Reaction Steps

A 25 mL Schlenk tube was replaced with Ar and 5-fluoro-7-propyl-8-trifluoromethanesulfonyloxyquinoline (1.00 g, 2.97 mmol), tetrakis(triphenylphosphine)palladium (171.3 mg, 0.148 mmol), 3.55 mL of piperidine and 2-methyl-3-butyn-2-ol (381 mg, 98 mass % article, 3.75 mmol) were added thereto and the mixture was stirred at 80° C. for 3 hours. The reaction mixture was cooled to room temperature, and then a saturated aqueous ammonium chloride solution was added thereto and the mixture was extracted with diethyl ether. The extract was dried over magnesium sulfate and the solvent was distilled off under reduced pressure by an evaporator. The crude reaction product was purified by column chromatography (Hexane/AcOEt=100/0→1/5) using silica gel to give 390 mg of dimethylhydroxymethyl-5-fluoro-7-propyl-8-quinolylacetylene as a yellowish brown solid (yield: 48.4%).

Provenance & Evidence