Potassium Carbonate → p-Tolyl 4-(5-chloro-6-fluoropyridin-3-yloxy)-2,5-difluorobenzoate

HRID 2048080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2048080
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:23]=[C:22](F)[C:21]([F:25])=[CH:20][C:9]=1[C:10]([O:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)=[O:11].[Cl:26][C:27]1[CH:28]=[C:29]([OH:34])[CH:30]=[N:31][C:32]=1[F:33]>CS(C)=O.CCOC(C)=O>[Cl:26][C:27]1[CH:28]=[C:29]([O:34][C:22]2[C:21]([F:25])=[CH:20][C:9]([C:10]([O:12][C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)=[O:11])=[C:8]([F:7])[CH:23]=2)[CH:30]=[N:31][C:32]=1[F:33]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 224515553-Chloro-2-fluoro-5-hydroxypyridineHCID 580424084-Methylphenyl 2,4,5-trifluorobenzoate

Produkt 1

HCID 58042398p-Tolyl 4-(5-chloro-6-fluoropyridin-3-yloxy)-2,5-difluorobenzoateAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Potassium carbonate (1.40 g, 10.14 mmol) was added to a solution of 4-Methylphenyl 2,4,5-trifluorobenzoate (Preparation 12, 1.80 g, 6.76 mmol), 5-chloro-6-fluoropyridin-3-ol (1.05 g, 7.10 mmol) in DMSO and the mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted in EtOAc (50 mL), washed with water (2×25 mL) and the organic layer dried over sodium sulfate, filtered, and concentrated in vacuo. The remaining crude was then purified by silica gel chromatography eluting with 10 to 50% EtOAc in heptane to afford the title compound (1.48 g, 56%):

Aufarbeitung

  1. washwashed with water (2×25 mL)
  2. dry with materialthe organic layer dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe remaining crude was then purified by silica gel chromatography
  6. washeluting with 10 to 50% EtOAc in heptane

Quellen und Nachweise

ORD-Eintrag
ord-7cec99d6b67a4b2b8fa8389d57b0cf6b
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592629B2

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