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 2048121Notes

Reaction equation

HRID 2048121 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 58042393(S)-tert-Butyl 5-chloro-4-((5-chloro-6-((1,1,1-trifluoropropan-2-yl)oxy)pyridin-3-yl)oxy)-2-fluorobenzoateYield 58.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-d068bf8968dc4366997578e0602ec724
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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