Reaktion #472776

Reaktionsgleichung

N-(2-chloro-5-fluoropyridin-3-yl)-2-methylacrylamide

water

chloroform

methanol

→

7-fluoro-4-methyl-1,5-naphthyridin-2(1H)-one

Lösungsmittel

N,N-dimethylformamide

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred for 2 hours
2. 2
   workup.STIRRINGthe mixture was stirred for 2 hours
3. 3
   TemperaturThe reaction mixture was cooled to room temperature
4. 4
   workup.DISTILLATIONthe solvent was then distilled off under reduced pressure, and diisopropyl ether and ethyl acetate
5. 5
   workup.ADDITIONwere added to the resultant residue
6. 6
   Filtrationthe solid was filtered off
7. 7
   Waschenwashed with ethyl acetate, to the solid
8. 8
   Sonstigethus obtained
9. 9
   Sonstigethe organic layer was separated
10. 10
    Extraktionthe aqueous layer was extracted with chloroform
11. 11
    Trocknenthe resultant solution was dried over anhydrous magnesium sulfate
12. 12
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure
13. 13
    workup.ADDITIONTo the resultant residue, diisopropyl ether was added
14. 14
    Filtrationthe solid was filtered off

Vorschrift

To a solution of 1.1 g of N-(2-chloro-5-fluoropyridin-3-yl)-2-methylacrylamide in 10 mL of N,N-dimethylformamide, 1.5 mL of triethylamine and 0.13 g of bis(tri-tert-butylphosphine)palladium(0) were added, and the mixture was stirred at 110° C. for 3 hours 40 minutes under a nitrogen flow. Thereto was further added 0.13 g of bis(tri-tert-butylphosphine)palladium(0), and the mixture was stirred for 2 hours. Thereto was further added 0.13 g of bis(tri-tert-butylphosphine)palladium(0), and the mixture was stirred for 2 hours. The reaction mixture was cooled to room temperature, the solvent was then distilled off under reduced pressure, and diisopropyl ether and ethyl acetate were added to the resultant residue, the solid was filtered off, and washed with ethyl acetate, to the solid thus obtained, water, chloroform and methanol were added, the organic layer was separated and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. To the resultant residue, diisopropyl ether was added, and the solid was filtered off to obtain 0.25 g of 7-fluoro-4-methyl-1,5-naphthyridin-2(1H)-one as a light brown solid.

Quelle