Citric Acid → HCID 58508786, compound

Participants

Reaction Steps

Water (0.6 mL), sodium carbonate (47 mg), 3-thiopheneboronic acid (27 mg), and bis(triphenylphosphine)palladium(II) dichloride (2.5 mg) were added to an ethylene glycol dimethyl ether (2.0 mL) solution of tert-butyl 4-bromo-2-(5-phenylpyridine-3-carboxamido)benzoate (80 mg), followed by heating to reflux under a nitrogen atmosphere for 2 hours and 10 minutes. The reaction mixture was cooled to room temperature, and then ethyl acetate and a 10% aqueous solution of citric acid was added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 95-85% hexane/ethyl acetate] to obtain tert-butyl 2-(5-phenylpyridine-3-carboxamido)-4-(thiophen-3-yl)benzoate.

Provenance & Evidence