Isopropyl iodide → ethyl 1-isopropyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate

HRID 82186

Reaktionsgleichung

Reaktionsgleichung von HRID 82186
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][NH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH:22]([CH3:24])[CH3:23]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]([F:13])([F:14])[F:12])=[N:9][N:8]([CH:22]([CH3:24])[CH3:23])[CH:7]=1)=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 596095Ethyl 3-(Trifluoromethyl)pyrazole-4-carboxylate

Produkt 1

HCID 57574507ethyl 1-isopropyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of 5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (13 g, 62.5 mmol) and cesium carbonate (61.1 g, 187.5 mmol) in DMF (70 mL) was added 2-iodo-propane (6.86 mL, 68.75 mmol) and the resulting mixture allowed to stir at room temperature for 16 hours. The crude reaction mixture was poured onto water (100 mL) and extracted with EtOAc (100 mL×3). The combined organics were washed with water (50 mL×2), brine (50 mL), dried over sodium sulphate, filtered and concentrated under reduced pressure to afford the title compound as an off-white solid in 65% yield, 10.2 g.

Aufarbeitung

  1. customThe crude reaction mixture
  2. additionwas poured onto water (100 mL)
  3. extractionextracted with EtOAc (100 mL×3)
  4. washThe combined organics were washed with water (50 mL×2), brine (50 mL)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-db3f9af732d44991838e63257ff6b3ca
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846698B2

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