Citric Acid → HCID 58508527, compound

Participants

Reaction Steps

Water (0.60 mL), thiophene-2-boronic acid (0.024 g), sodium carbonate (0.041 g), and bis(triphenylphosphine)palladium(II) dichloride (2.2 mg) were added to an ethylene glycol dimethyl ether (2.0 mL) solution of tert-butyl 2-(2-acetoxy-5-(piperidin-1-yl)benzamido)-4-bromobenzoate (0.080 g), followed by heating to reflux under a nitrogen atmosphere for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and a 10% aqueous solution of citric acid and ethyl acetate were 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 [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 95-85% hexane/ethyl acetate] to obtain 0.027 g of tert-butyl 2-(2-hydroxy-5-(piperidin-1-yl)benzamido)-4-(thiophen-2-yl)benzoate as a yellow solid.

Provenance & Evidence