反应详情

Ethanol (0.62 mL), water (0.31 mL), sodium carbonate (70 mg), 1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole (55 mg), and tetrakis(triphenylphosphine)palladium(0) (13 mg) were added to a toluene (2.1 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 2 hours. The reaction mixture was cooled to room temperature, and then sodium carbonate (23 mg), 1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole (46 mg), and tetrakis(triphenylphosphine)palladium(0) (13 mg) were added thereto, followed by heating to reflux under a nitrogen atmosphere for 3 hours and 30 minutes. The reaction mixture was cooled to room temperature, and then toluene (1.0 mL), ethanol (0.31 mL), and water (0.16 mL) 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 a 10% aqueous solution of citric acid 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: 95-85% hexane/ethyl acetate] to obtain 71 mg of tert-butyl 4-(1-methyl-1H-pyrrol-2-yl)-2-(5-phenylpyridine-3-carboxamido)benzoate as a light yellow solid.

1. temperatureby heating
2. temperatureto reflux under a nitrogen atmosphere for 2 hours
3. temperatureby heating
4. temperatureto reflux under a nitrogen atmosphere for 3 hours and 30 minutes
5. temperatureThe reaction mixture was cooled to room temperature
6. temperatureby heating
7. temperatureto reflux under a nitrogen atmosphere for 2 hours
8. temperatureThe reaction mixture was cooled to room temperature
9. customThe organic layer was separated
10. washwashed with a saturated aqueous solution of sodium chloride
11. dry with materialdried over anhydrous magnesium sulfate
12. customthe solvent was evaporated under reduced pressure
13. customThe obtained residue was purified by silica gel column chromatography [eluent: 95-85% hexane/ethyl acetate]