Citric Acid → HCID 66990697, compound

Participants

Reaction Steps

Water (0.6 mL), sodium carbonate (58 mg), tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbonate (85 mg), and bis(triphenylphosphine)palladium(II) dichloride (3.0 mg) were added to an ethylene glycol dimethyl ether (2.0 mL) suspension of tert-butyl 4-bromo-2-(5-phenylpyridine-3-carboxamido)benzoate (0.10 g), followed by heating to reflux under a nitrogen atmosphere for 1 hour. The reaction mixture was cooled to room temperature, and then ethyl acetate and a 10% aqueous solution of citric acid 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 [eluent: 95-80% hexane/ethyl acetate] to obtain tert-butyl 4-(3-(tert-butoxycarbonyl)oxyphenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate.

Provenance & Evidence