Acetic Acid → 2-(4-Methoxyquinolin-6-yl)-1-(6-methylpyridin-2-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

To a 20 mL threaded pressure tube was added 6–Chloro-4-methoxy-quinoline (298 mg, 1.54 mmol), palladium (II) acetate (7 mg, 0.03 mmol), 2-Dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (a.k.a. AMPHOS, 24 mg, 0.06 mmol), and potassium tert-butoxide (1M in THF, 3.7 mmol). This mixture was stirred and 1-(6-Methyl-pyridin-2-yl)-ethanone was added. The pressure tube was then sealed and heated to 70° C. The reaction mixture was stirred at 70° C. for 18 hours. LC-MS showed product. The reaction mixture was then cooled and poured into a solution of 600 μL of glacial acetic acid in 30 mL of water. Title compound was extracted with 3×30 mL of chloroform. The organic layers were combined, dried over sodium sulfate, filtered, and concentrated via rotary evaporator. The residue was purified by flash column chromatography (silica gel) using a 1% Methanol/Chloroform solvent system affording 255 mg of desired product (56% yield). HPLC=4.39 min, LC-MS=293 (M+H, mw=292.34).

Provenance & Evidence