Potassium Carbonate → 5-(3-Trifluoromethyl-pyrazol-1-yl)-pyridine-2-carboxylic acid methyl ester

HRID 1255791Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1255791
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](Cl)=[CH:7][N:6]=1)=[O:4].[F:12][C:13]([F:20])([F:19])[C:14]1[CH:18]=[CH:17][NH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:16]2[CH:17]=[CH:18][C:14]([C:13]([F:20])([F:19])[F:12])=[N:15]2)=[CH:7][N:6]=1)=[O:4]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 18070343-(Trifluoromethyl)pyrazoleHCID 11298216Methyl 5-chloropyridine-2-carboxylate

Produkt 1

HCID 574965955-(3-Trifluoromethyl-pyrazol-1-yl)-pyridine-2-carboxylic acid methyl esterAusbeute 3,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A mixture of 5-chloro-pyridine-2-carboxylic acid methyl ester (1.37 g), 3-trifluoromethyl-1H-pyrazole (1.63 g) and powdered K2CO3 (1.67 g) in DMF (20 ml) was heated to 105° C. for 20 h. The mixture was evaporated and the residue partitioned between water and dichloromethane, the organic layer was washed with water, dried and evaporated. The residue was chromatographed on silica using n-heptane/ethyl acetate (gradient from 3:1 to 1:1) to give 5-(3-trifluoromethyl-pyrazol-1-yl)-pyridine-2-carboxylic acid methyl ester (70 mg) as a colorless solid. MS (ESI): m/z=272.1 [ M+H]+.

Aufarbeitung

  1. customThe mixture was evaporated
  2. customthe residue partitioned between water and dichloromethane
  3. washthe organic layer was washed with water
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on silica

Quellen und Nachweise

ORD-Eintrag
ord-03dbbf478e74446dadac04aaf8e86fd9
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461160B2

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