2-Chlorophenol → HCID 50908543, compound

HRID 1846949Notes

Reaction equation

HRID 1846949 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

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-e1d3634133d54cf5aeb2f0e53e014376
Source dataset
uspto-grants-2015_02
Patent number
US08952034B2

Reaction notes

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