Water → Ethyl 1-(3-chloro-2-pyridinyl)-3-(2,2,2-trifluoroethoxy)-1H-pyrazole-5-carboxylate

HRID 516526Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 516526
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][C:10](=[O:18])[NH:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[CH2:31][C:32]([F:35])([F:34])[F:33])(=O)=O.O>C(#N)C>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][C:10]([O:18][CH2:31][C:32]([F:35])([F:34])[F:33])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 21113391Ethyl 2-(3-chloro-2-pyridinyl)-2,5-dihydro-5-oxo-1H-pyrazole-3-carboxylate2×

Produkt 1

HCID 21113392Ethyl 1-(3-chloro-2-pyridinyl)-3-(2,2,2-trifluoroethoxy)-1H-pyrazole-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a suspension of ethyl 1-(3-chloro-2-pyradinyl)-2,3-dihydro-3-oxo-1H-pyrazole-5-carboxylate (i.e. product of Step A) (0.8 g, 3 mmol) stirred in dry acetonitrile (15 mL) at −5° C. was added potassium carbonate (0.85 g, 6.15 mmol). The suspension was stirred for 15 minutes at 20° C. The stirred suspension was then cooled to 5° C., and 2,2,2-trifluoro-ethyl trifluoromethanesulfonate (0.8 g, 3.45 mmol) was added dropwise. The reaction mixture was warmed to room temperature and then heated to reflux, at which time thin layer chromatography showed the reaction to be complete. Water (25 mL) was added to the reaction mixture, which was then extracted with ethyl ether. The ether extract was dried over magnesium sulfate and concentrated to yield the title product compound (1.05 g) as a pale yellow oil.

Aufarbeitung

  1. temperatureThe stirred suspension was then cooled to 5° C.
  2. temperatureThe reaction mixture was warmed to room temperature
  3. temperatureheated
  4. temperatureto reflux, at which time thin layer chromatography
  5. customthe reaction
  6. extractionwas then extracted with ethyl ether
  7. extractionThe ether extract
  8. dry with materialwas dried over magnesium sulfate
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-08acf2dc00d74ec1929f74ede0468e91
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09113630B2

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