Reaktion #53451

Reaktionsgleichung

potassium carbonate

ethyl 3-ethoxy-2-(3-bromo-2,4,5-trifluorobenzoyl)acrylate

ethyl 3-bromo-2,4,5-trifluorobenzoylacetate

2-amino-6-(t-butylamino) -3,5-difluoropyridine

amino acrylate

→

title compound

ethyl 8-bromo-1-[6-(t-butylamino)-3,5-difluoropyridin-2-yl]-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Lösungsmittel

N,N-dimethylformamide

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONwas dissolved
2. 2
   EinengenThe reaction mixture was concentrated under reduced pressure
3. 3
   Sonstigeto obtain a yellow solid residue
4. 4
   Temperaturto cool down
5. 5
   workup.DISTILLATIONChloroform (30 mL) and distilled water (300 mL)
6. 6
   workup.ADDITIONwere added
7. 7
   Sonstigeto separate into layers
8. 8
   WaschenThe chloroform layer was washed twice with distilled water (300 mL)
9. 9
   Trocknendried over anhydrous magnesium sulfate
10. 10
    Einengenconcentrated under reduced pressure
11. 11
    workup.WAITleft over
12. 12
    FiltrationThe precipitate was collected by filtration
13. 13
    Waschenwashed successively with ethanol and diisopropyl ether in this order

Vorschrift

To a chloroform solution (5 mL) in which ethyl 3-ethoxy-2-(3-bromo-2,4,5-trifluorobenzoyl)acrylate prepared from ethyl 3-bromo-2,4,5-trifluorobenzoylacetate (1.32 g) in a manner known per se in the art was dissolved, 2-amino-6-(t-butylamino) -3,5-difluoropyridine was added under TLC monitoring of the reaction until conversion into an amino acrylate derivative was completed. The reaction mixture was concentrated under reduced pressure to obtain a yellow solid residue. To the residue, anhydrous potassium carbonate (1.2 g) and N,N-dimethylformamide (2 mL) were added, and the mixture was stirred at 90° for 15 minutes. The mixture was allowed to cool down. Chloroform (30 mL) and distilled water (300 mL) were added, and the mixture was allowed to separate into layers. The chloroform layer was washed twice with distilled water (300 mL), dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and then left over. The precipitate was collected by filtration, and washed successively with ethanol and diisopropyl ether in this order to obtain the title compound (1.41 g) as a colorless powder.

Quelle