Potassium Carbonate → (S)-tert-Butyl 5-chloro-4-((5-chloro-6-((1,1,1-trifluoropropan-2-yl)oxy)pyridin-3-yl)oxy)-2-fluorobenzoate

HRID 2048121Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2048121
[Cl:1][C:2]1[C:3](F)=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[Cl:17][C:18]1[CH:19]=[C:20]([OH:31])[CH:21]=[N:22][C:23]=1[O:24][C@@H:25]([CH3:30])[C:26]([F:29])([F:28])[F:27].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:1][C:2]1[C:3]([O:31][C:20]2[CH:21]=[N:22][C:23]([O:24][C@@H:25]([CH3:30])[C:26]([F:29])([F:28])[F:27])=[C:18]([Cl:17])[CH:19]=2)=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 580424575-chloro-6-[(1S)-2,2,2-trifluoro-1-methylethoxy]pyridin-3-olHCID 58042499Tert-butyl 5-chloro-2,4-difluorobenzoate

Produkt 1

HCID 58042393(S)-tert-Butyl 5-chloro-4-((5-chloro-6-((1,1,1-trifluoropropan-2-yl)oxy)pyridin-3-yl)oxy)-2-fluorobenzoateAusbeute 58,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

tert-Butyl 5-chloro-2,4-difluorobenzoate (Preparation 59, 8.3 g, 33.4 mmol) was added to a solution of 5-chloro-6-[(1S)-2,2,2-trifluoro-1-methylethoxy]pyridin-3-ol (Preparation 231, 16.2 g, 66.8 mmol) and potassium carbonate (27.8 g, 200 mmol) in dimethyl sulfoxide (100 mL). The reaction mixture was stirred at room temperature for 18 hours then quenched with an aqueous solution of sodium hydroxide (1 M, 100 mL). A white precipitate formed and was collected by filtration to give the title compound as a white solid (9.2 g).

Aufarbeitung

  1. customthen quenched with an aqueous solution of sodium hydroxide (1 M, 100 mL)
  2. customA white precipitate formed
  3. filtrationwas collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-d068bf8968dc4366997578e0602ec724
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592629B2

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