Triphenylphosphine → 7-Bromo-5-(2-(quinolin-2-yl)ethyl)furo[3,2-c]pyridin-4(5H)-one

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Reaction Steps

DIAD (4.91 mmol, 992 mg) was added dropwise to PPh3 (753 mg, 2.80 mmol) in 20 mL of THF. The mixture was stirred for 30 min. Then 7-bromofuro[3,2-c]pyridine-4(5H)-one (300 mg, 1.402 mmol) was added followed by the addition of 2-(quinolin-2-yl)ethanol (243 mg, 1.402 mmol). The reaction mixture was stirred overnight at room temperature. The reaction mixture was extracted with water/ethyl acetate. The organic phase was extracted with 1N HCl. The acidic aqueous phase was basified with 1N NaOH and extracted with DCM. The organic phase was extracted with water, dried over MgSO4, filtered, concentrated and purified by chromatography to give the title compound as white solid (119 mg, 23%).

Provenance & Evidence