Citric Acid → HCID 58508797, compound

Participants

Reaction Steps

Cesium carbonate (0.14 g), morpholine (0.029 mL), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (5 mg), tris(dibenzylideneacetone)dipalladium(0) (2 mg), and palladium(II) acetate (1 mg) were added to a toluene (3.0 mL) solution 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 morpholine (0.029 mL) was added thereto, followed by heating to reflux under a nitrogen atmosphere for 2 hours. The reaction mixture was cooled to room temperature, and then cesium carbonate (72 mg), morpholine (0.029 mL), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (5 mg), tris(dibenzylideneacetone)dipalladium(0) (2 mg), and palladium(II) acetate (1 mg) were added thereto, followed by heating to reflux under a nitrogen atmosphere for 4 hours. 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: 85-70% hexane/ethyl acetate] to obtain tert-butyl 4-morpholino-2-(5-phenylpyridine-3-carboxamido)benzoate.

Provenance & Evidence