2-Chlorophenol → HCID 50908543, compound

HRID 2205743Notes

Reaction equation

HRID 2205743 reaction equation
[F:1][C:2]([C:10]1[N:14]2[CH:15]=[C:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=3)[CH:17]=[CH:18][C:13]2=[N:12][N:11]=1)([F:9])[CH2:3][O:4][CH2:5][CH:6]1[CH2:8][O:7]1.[Cl:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[OH:37].C(=O)([O-])[O-].[K+].[K+].[H-].[Na+]>CC(C)=O.CN(C=O)C>[Cl:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[O:37][CH2:8][CH:6]([OH:7])[CH2:5][O:4][CH2:3][C:2]([F:9])([F:1])[C:10]1[N:14]2[CH:15]=[C:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]([F:27])([F:28])[F:29])=[CH:21][CH:20]=3)[CH:17]=[CH:18][C:13]2=[N:12][N:11]=1

Participants

7

Reactant 4

HCID 72452-ChlorophenolHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 86650232HCID 86650232, compound

Product 1

HCID 50908543HCID 50908543, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

1 To a round bottom flask was added 3-(1,1-difluoro-2-(oxiran-2-ylmethoxy)ethyl)-6-(4-(trifluoromethoxy)phenyl)[1,2,4]triazolo[4,3-a]pyridine, prepared as described in Example 15, and 2-chlorophenol in acetone followed by potassium carbonate (sodium hydride in DMF at RT will also work). The reaction mixture was refluxed overnight. Potassium carbonate was filtered off. The filtrate was concentrated down and purified by prep TLC followed by prep HPLC to afford 1-(2-chlorophenoxy)-3-(2,2-difluoro-2-(6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)ethoxy)propan-2-ol.

Workup

  1. customprepared
  2. customat RT
  3. temperatureThe reaction mixture was refluxed overnight
  4. filtrationPotassium carbonate was filtered off
  5. concentrationThe filtrate was concentrated down
  6. custompurified by prep TLC

Sources & evidence

ORD record
ord-f6cfdfb5ef2b4ff89b17040afe1008a6
Source dataset
uspto-grants-2016_06
Patent number
US09371329B2

Reaction notes

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