Reaktion #158328

Reaktionsgleichung

ammonium chloride

ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

sodium hydride

N-fluoro-N′-chloromethyltriethylenediamine bis(tetrafluoroborate)

→

title compound

Ausbeute 60.6%

ethyl 8-fluoro-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

Ausbeute 60.6%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   Temperaturcooling
3. 3
   Temperaturcooling
4. 4
   workup.STIRRINGthe mixture was stirred for 30 min under ice-
5. 5
   Temperaturcooling
6. 6
   Extraktionthe mixture was extracted with ethyl acetate
7. 7
   WaschenThe extract was washed with saturated brine
8. 8
   Trocknendried over anhydrous sodium sulfate
9. 9
   Sonstigethe solvent was evaporated under reduced pressure
10. 10
    SonstigeThe residue was purified by silica gel column chromatography (methanol/ethyl acetate)

Vorschrift

Under an argon atmosphere, ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (200 mg) was added to a suspension of sodium hydride (60%, 23 mg) in DMF (2 mL) under ice-cooling. The reaction mixture was stirred for 30 min under ice-cooling, N-fluoro-N′-chloromethyltriethylenediamine bis(tetrafluoroborate) (371 mg) was added under ice-cooling, and the mixture was stirred for 30 min under ice-cooling. The reaction mixture was poured into saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (127 mg).

Quelle