Potassium Carbonate → HCID 58042385, Verbindung

HRID 2048084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2048084
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:9](F)=[CH:10][C:11]([F:21])=[C:12]([CH:20]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[Cl:23][C:24]1[CH:25]=[C:26]([OH:38])[CH:27]=[N:28][C:29]=1[O:30][CH2:31][C:32]([F:37])([F:36])[CH:33]([F:35])[F:34].COC(C)(C)C>CS(C)=O>[Cl:7][C:8]1[C:9]([O:38][C:26]2[CH:27]=[N:28][C:29]([O:30][CH2:31][C:32]([F:36])([F:37])[CH:33]([F:35])[F:34])=[C:24]([Cl:23])[CH:25]=2)=[CH:10][C:11]([F:21])=[C:12]([CH:20]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 15413tert-Butyl methyl etherHCID 580423945-Chloro-6-(2,2,3,3-tetrafluoropropoxy)pyridin-3-olHCID 58042499Tert-butyl 5-chloro-2,4-difluorobenzoate

Produkt 1

HCID 58042385HCID 58042385, VerbindungAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Potassium carbonate (3.02 g, 21.85 mmol) was added portionwise to a suspension of tert-butyl 5-chloro-2,4-difluorobenzoate (Preparation 59, 2.26 g, 9.09 mmol), 5-chloro-6-(2,2,3,3-tetrafluoropropoxy)pyridin-3-ol (Preparation 73, 2.25 g, 8.67 mmol) in DMSO (13.5 mL). The mixture was stirred at room temperature under nitrogen for 3 hours. tert-butyl methyl ether (50.0 mL) was added and the mixture was washed with water (3×50.0 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting oil was suspended with heptane (20.0 mL) and concentrated in vacuo. The resulting solid was suspended in heptane (20.0 mL) and heated to 90° C. until full dissolution. The mixture was cooled with stirring and the residual solid collected by filtration. The filtrate was concentrated in vacuo and the resulting solid was suspended in heptane (10.0 mL) and heated to 90° C. until dissolution. The mixture was again cooled with stirring and the residual solid collected by filtration. The two crops were combined to yield the title compound as a white solid (2.58 g, 5.29 mmol, 61%):

Aufarbeitung

  1. washthe mixture was washed with water (3×50.0 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. concentrationconcentrated in vacuo
  6. temperatureheated to 90° C. until full dissolution
  7. temperatureThe mixture was cooled
  8. stirringwith stirring
  9. filtrationthe residual solid collected by filtration
  10. concentrationThe filtrate was concentrated in vacuo
  11. temperatureheated to 90° C. until dissolution
  12. temperatureThe mixture was again cooled
  13. stirringwith stirring
  14. filtrationthe residual solid collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-1aaa9902cbb2402f9a3e1bd58b355198
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592629B2

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