Cesium carbonate → Ethyl 1-(2-fluoroethyl)-1H-pyrazole-5-carboxylate

HRID 244669

Reaktionsgleichung

Reaktionsgleichung von HRID 244669
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[N:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:17][CH2:18][CH2:19]I>C(#N)C>[F:17][CH2:18][CH2:19][N:2]1[C:3]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:5]=[N:1]1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 69804Ethane, 1-fluoro-2-iodo-HCID 178469268HCID 178469268, Verbindung

Produkt 1

HCID 58356443Ethyl 1-(2-fluoroethyl)-1H-pyrazole-5-carboxylateAusbeute 41,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of ethyl 1H-pyrazole-3-carboxylate (0.77 g) (available from ABCR) in acetonitrile (30 ml) was added cesium carbonate (1.79 g) and the mixture stirred for 5 min when 1-fluoro-2-iodoethane (0.96 g) was added and the mixture stirred at 20° C. for 18 h. The mixture was evaporated and the residue taken up in water (30 ml) and DCM (30 ml) separated by hydrophobic frit and concentrated to ˜5 ml, placed on an SPE cartridge (50 g silica) and eluted with a gradient of ethyl acetate in cyclohexane to give the Ethyl 1-(2-fluoroethyl)-1H-pyrazole-5-carboxylate (0.42 g) as a colourless oil.

Aufarbeitung

  1. additionwas added
  2. customThe mixture was evaporated
  3. customDCM (30 ml) separated by hydrophobic frit
  4. concentrationconcentrated to ˜5 ml
  5. washeluted with a gradient of ethyl acetate in cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-a3a04461567e418a95a2dc047cba8e48
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658635B2

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