反应详情

温度

80 °C

Methyl 7-(4-(tert-butoxycarbonyl)phenyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate. To a mixture of methyl 7-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate (Method 7) (3.82 g, 12.2 mmol), 4-(tert-butoxycarbonyl)phenylboronic acid (2.72 g, 12.2 mmol), cesium fluoride (5.58 g, 36.7 mmol), and tetrakis(triphenylphosphine)palladium [0] (0.424 g, 0.367 mmol) in a vial, was added MeOH (61 mL). The vial was sealed and heated at 80° C. for 2 hours. The reaction mixture was then cooled, diluted with 200 mL of EtOAc, added to a separatory funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed 2 times with 75 mL of sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, and concentrated via rotary evaporation to give the product. The resulting product was purified via flash chromatography (silica gel) to provide the title compound as an off-white solid.

1. customThe vial was sealed
2. temperatureThe reaction mixture was then cooled
3. additionadded to a separatory funnel
4. custompartitioned with sodium bicarbonate (saturated, aqueous)
5. washwashed 2 times with 75 mL of sodium bicarbonate (saturated, aqueous)
6. customseparated
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated via rotary evaporation
9. customto give the product
10. customThe resulting product was purified via flash chromatography (silica gel)