반응 #640719

반응 방정식

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

용매

MeOH

EtOAc

반응 조건

후처리

1. 1
   기타The vial was sealed
2. 2
   온도The reaction mixture was then cooled
3. 3
   workup.ADDITIONadded to a separatory funnel
4. 4
   기타partitioned with sodium bicarbonate (saturated, aqueous)
5. 5
   세척washed 2 times with 75 mL of sodium bicarbonate (saturated, aqueous)
6. 6
   기타separated
7. 7
   건조dried over sodium sulfate
8. 8
   농축concentrated via rotary evaporation
9. 9
   기타to give the product
10. 10
    기타The resulting product was purified via flash chromatography (silica gel)

실험 절차

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.

출처