反应 #640719

反应方程式

Methyl 7-(4-(tert-butoxycarbonyl)phenyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate

methyl 7-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate

4-(tert-butoxycarbonyl)phenylboronic acid

cesium fluoride

→

title compound

4-(3-(3-Carboxypropanoyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-7-yl)benzoic acid

溶剂

MeOH

EtOAc

反应条件

后处理

1. 1
   其他The vial was sealed
2. 2
   温度The reaction mixture was then cooled
3. 3
   workup.ADDITIONadded to a separatory funnel
4. 4
   其他partitioned with sodium bicarbonate (saturated, aqueous)
5. 5
   洗涤washed 2 times with 75 mL of sodium bicarbonate (saturated, aqueous)
6. 6
   其他separated
7. 7
   干燥dried over sodium sulfate
8. 8
   浓缩concentrated via rotary evaporation
9. 9
   其他to give the product
10. 10
    其他The resulting product was purified via flash chromatography (silica gel)

实验过程

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.

来源