반응 #51831

반응 방정식

8-bromo-4-(4-isopropyloxycarbonyl-1,2,3,6-tetrahydropyridin-1-yl)-2-methylquinoline

sodium carbonate

water

2,4-dichlorophenylboric acid

→

title compound

8-(2,4-dichlorophenyl)-4-(4-isopropyloxycarbonyl-1,2,3,6-tetrahydropyridin-1-yl)-2-methylquinoline

용매

ethanol

toluene

반응 조건

후처리

1. 1
   workup.ADDITIONby adding
2. 2
   온도under reflux for 5 hours
3. 3
   기타to be separated
4. 4
   추출After the aqueous phase was extracted with ethyl acetate
5. 5
   건조the combined organic phase was dried over anhydrous sodium sulfate
6. 6
   여과The desiccating agent was filtered off
7. 7
   농축after which the filtrate was concentrated under reduced pressure
8. 8
   기타the resultant residue was crystallized from diisopropyl ether
9. 9
   여과The crystals were collected by filtration
10. 10
    세척washed with a small amount of diisopropyl ether

실험 절차

Under a nitrogen atmosphere, 8-bromo-4-(4-isopropyloxycarbonyl-1,2,3,6-tetrahydropyridin-1-yl)-2-methylquinoline (5.9 g), 2,4-dichlorophenylboric acid (3.2 q) and sodium carbonate (4.8 g) were suspended in a mixed solvent of deaerated water (15 mL), toluene (7.5 mL) and ethanol (7.5 mL), followed by adding thereto tetrakis(triphenylphosphine)palladium (0.88 g), and the resulting mixture was heated under reflux for 5 hours. The reaction mixture was cooled to room temperature to be separated. After the aqueous phase was extracted with ethyl acetate, the combined organic phase was dried over anhydrous sodium sulfate. The desiccating agent was filtered off, after which the filtrate was concentrated under reduced pressure and the resultant residue was crystallized from diisopropyl ether. The crystals were collected by filtration and washed with a small amount of diisopropyl ether to obtain the title compound (5.3 g).

출처