反应详情

Phenylboranic acid (21 mg), tripotassium phosphate (69 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.2 mg), and palladium(II) acetate (1.3 mg) were added to a toluene (1.2 mL) solution of tert-butyl 2-(4-chloropyridine-2-carboxamido)-4-phenylbenzoate (60 mg), followed by heating to reflux under a nitrogen atmosphere for 3 hours. The reaction mixture was cooled to room temperature, and then phenylboranic acid (5.4 mg), tripotassium phosphate (16 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.2 mg), and palladium(II) acetate (1.3 mg) were added thereto, followed by heating to reflux under a nitrogen atmosphere for 2 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 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 [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 100-85% hexane/ethyl acetate] to obtain 65 mg of tert-butyl 4-phenyl-2-(4-phenylpyridine-2-carboxamido)benzoate as a colorless oily substance.

1. temperatureby heating
2. temperatureto reflux under a nitrogen atmosphere for 3 hours
3. temperatureby heating
4. temperatureto reflux under a nitrogen atmosphere for 2 hours
5. temperatureThe reaction mixture was cooled to room temperature
6. customThe insoluble substance was removed by filtration
7. customThe organic layer was separated
8. washwashed with a saturated aqueous solution of sodium chloride
9. dry with materialdried over anhydrous magnesium sulfate
10. customthe solvent was evaporated under reduced pressure
11. customThe obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 100-85% hexane/ethyl acetate]