Ethyl Acetate → tert-Butyl 4-({5-chloro-6-[(3,3-difluorocyclobutyl)methoxy]pyridin-3-yl}oxy)-2,5-difluorobenzoate

HRID 2048038Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2048038
[F:1][C:2]1[CH:14]=[C:13](F)[C:12]([F:16])=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[Cl:17][C:18]1[CH:19]=[C:20]([OH:32])[CH:21]=[N:22][C:23]=1[O:24][CH2:25][CH:26]1[CH2:29][C:28]([F:31])([F:30])[CH2:27]1.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CS(C)=O>[Cl:17][C:18]1[CH:19]=[C:20]([O:32][C:13]2[C:12]([F:16])=[CH:11][C:3]([C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[C:2]([F:1])[CH:14]=2)[CH:21]=[N:22][C:23]=1[O:24][CH2:25][CH:26]1[CH2:27][C:28]([F:30])([F:31])[CH2:29]1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 10868153Tert-butyl 2,4,5-trifluorobenzoateHCID 580423895-Chloro-6-((3,3-difluorocyclobutyl)methoxy)pyridin-3-OL

Produkt 1

HCID 58042465tert-Butyl 4-({5-chloro-6-[(3,3-difluorocyclobutyl)methoxy]pyridin-3-yl}oxy)-2,5-difluorobenzoateAusbeute 101 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

tert-Butyl 2,4,5-trifluorobenzoate (Preparation 6, 0.200 g, 0.86 mmol), 5-chloro-6-[(3,3-difluorocyclobutyl)methoxy]pyridin-3-ol (Preparation 5, 0.258 g, 1.03 mmol) and potassium carbonate (0.178 g, 1.29 mmol) were suspended in DMSO (5.0 mL). The mixture was stirred at room temperature under nitrogen for 16 hours. EtOAc (50 mL) was added and the mixture was washed with water (3×150 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound (0.400 g, 101%):

Aufarbeitung

  1. washthe mixture was washed with water (3×150 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d8b963e3398e4a6887ec3f3ed0853f96
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592629B2

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