Potassium Carbonate → Methyl 5-(2,2-difluoroethoxy)-3-methylpyrazine-2-carboxylate

HRID 627704Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627704
Cl[C:2]1[N:3]=[C:4]([CH3:12])[C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[F:13][CH:14]([F:17])[CH2:15][OH:16].C(=O)([O-])[O-].[K+].[K+]>O>[F:13][CH:14]([F:17])[CH2:15][O:16][C:2]1[N:3]=[C:4]([CH3:12])[C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 1361872,2-Difluoroethan-1-olHCID 72218580Methyl 5-chloro-3-methylpyrazine-2-carboxylate

Produkt 1

HCID 86728150Methyl 5-(2,2-difluoroethoxy)-3-methylpyrazine-2-carboxylateAusbeute 20,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of methyl 5-chloro-3-methylpyrazine-2-carboxylate (255 mg, 1.367 mmol) in 2,2-difluoroethanol (0.52 mL, 8.20 mmol) was added potassium carbonate (227 mg, 1.640 mmol). The reaction was stirred at ambient temperature for 1.5 hrs. The reaction was treated with water and extracted with ethyl acetate. The organic portion was dried over Na2SO4, filtered, concentrated and purified by column chromatography, eluting with 0-2% MeOH/DCM to give the title compound (63.8 mg, 0.275 mmol, 20.1%). MS m/z=233.1 (M+H).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic portion was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by column chromatography
  6. washeluting with 0-2% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-268f8a4fb9ae4328941255e471e9b755
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309263B2

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