1,2-Dimethoxyethane → HCID 66990481, compound

Participants

Reaction Steps

Ethylene glycol dimethyl ether (12 mL), water (3.6 mL), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.49 g), sodium carbonate (0.50 g), and bis(triphenylphosphine)palladium(II) dichloride (14 mg) were added to tert-butyl 2-(2-(benzyloxy)-4-iodobenzamido)-4-phenylbenzoate (1.2 g), followed by heating to reflux under a nitrogen atmosphere for 2 hours. The reaction mixture was cooled to room temperature, and bis(triphenylphosphine)palladium(II) dichloride (28 mg) was added thereto, followed by heating to reflux under a nitrogen atmosphere for 4 hours. The reaction mixture was cooled to room temperature, and bis(triphenylphosphine)palladium(II) dichloride (28 mg) was added thereto, followed by heating to reflux under a nitrogen atmosphere for 4 hours. The reaction mixture was cooled to room temperature, and water 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 [eluent: 80-60% hexane/ethyl acetate] to obtain 0.55 g of tert-butyl 2-(2-(benzyloxy)-4-(pyridin-4-yl)benzamido)-4-phenylbenzoate as a white solid.

Provenance & Evidence