Citric Acid → HCID 66990470, compound

Participants

Reaction Steps

Morpholine (0.014 mL), cesium carbonate (0.070 g), tris(dibenzylideneacetone)dipalladium(0) (1.0 mg), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (2.6 mg), and palladium(II) acetate (0.5 mg) were added to a toluene (0.90 mL) solution of tert-butyl 2-(2-(benzyloxy)-5-bromobenzamido)-4-phenylbenzoate (0.060 g), followed by heating to reflux under a nitrogen atmosphere for 2 hours and 30 minutes. The reaction mixture was cooled to room temperature, and then morpholine (4.7 μL), cesium carbonate (0.035 g), tris(dibenzylideneacetone)dipalladium(0) (1.0 mg), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (2.6 mg), and palladium(II) acetate (0.5 mg) were added thereto, followed by heating to reflux under a nitrogen atmosphere for 2 hours 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 insoluble substance was removed by filtration. 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: 100-60% hexane/ethyl acetate] to obtain 0.060 g of tert-butyl-2-(2-(benzyloxy)-5-(morpholin-4-yl)benzamido)-4-phenylbenzoate as a light yellow solid.

Provenance & Evidence