Reaktion #51831

Reaktionsgleichung

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

Lösungsmittel

ethanol

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONby adding
2. 2
   Temperaturunder reflux for 5 hours
3. 3
   Sonstigeto be separated
4. 4
   ExtraktionAfter the aqueous phase was extracted with ethyl acetate
5. 5
   Trocknenthe combined organic phase was dried over anhydrous sodium sulfate
6. 6
   FiltrationThe desiccating agent was filtered off
7. 7
   Einengenafter which the filtrate was concentrated under reduced pressure
8. 8
   Sonstigethe resultant residue was crystallized from diisopropyl ether
9. 9
   FiltrationThe crystals were collected by filtration
10. 10
    Waschenwashed with a small amount of diisopropyl ether

Vorschrift

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).

Quelle