Potassium Carbonate → 2-Pyrazinecarboxylic acid, 5-(difluoromethoxy)-, methyl ester

HRID 571684Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571684
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([OH:11])=[CH:7][N:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl[C:19]([F:24])([F:23])C([O-])=O.[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([O:11][CH:19]([F:24])[F:23])=[CH:7][N:6]=1)=[O:4]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 2734985Sodium chlorodifluoroacetateHCID 178498852HCID 178498852, Verbindung

Produkt 1

HCID 578272862-Pyrazinecarboxylic acid, 5-(difluoromethoxy)-, methyl esterAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To 5-hydroxypyrazine-2-carboxylic acid methyl ester (2.0 g, 13 mmol) in a glass tube reaction vessel in DMF (26 mL) was added potassium carbonate (5.3 g, 39 mmol) and sodium 2-chloro-2,2-difluoroacetate (4.0 g, 26 mmol). The reaction vessel was capped and warmed to 100° C. The reaction was stirred for 30 minutes and cooled to room temperature. The reaction was filtered washing with EtOAc. The filtrate was concentrated in vacuo. The residue was taken up into EtOAc and washed with brine. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-40% EtOAc/hex) to give methyl-5-(difluoromethoxy)pyrazine-2-carboxylate (0.09 g, 0.46 mmol) (0.40 g, 20%).

Aufarbeitung

  1. customThe reaction vessel was capped
  2. temperaturecooled to room temperature
  3. filtrationThe reaction was filtered
  4. washwashing with EtOAc
  5. concentrationThe filtrate was concentrated in vacuo
  6. washwashed with brine
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel chromatography (0-40% EtOAc/hex)

Quellen und Nachweise

ORD-Eintrag
ord-54a46a51e9eb40d1978da4ca3d3e3373
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029362B2

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