Cesium carbonate → 5-(benzyloxy)-3-(3-fluoro-2-(trifluoromethyl)phenyl)-3H-imidazo[4,5-b]pyridine

HRID 1890324Notes

Reaction equation

HRID 1890324 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]2[NH:15][CH:16]=[N:17][C:12]2=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21](F)[C:20]=1[C:26]([F:29])([F:28])[F:27].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOCC>[CH2:1]([O:8][C:9]1[N:14]=[C:13]2[N:15]([C:21]3[CH:22]=[CH:23][CH:24]=[C:19]([F:18])[C:20]=3[C:26]([F:27])([F:29])[F:28])[CH:16]=[N:17][C:12]2=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 156142331,3-Difluoro-2-(trifluoromethyl)benzeneHCID 178420377HCID 178420377, compound

Product 1

HCID 673123105-(benzyloxy)-3-(3-fluoro-2-(trifluoromethyl)phenyl)-3H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

5-(Benzyloxy)-3H-imidazo[4,5-b]pyridine (0.10 g, 0.44 mmol) and 1,3-difluoro-2-(trifluoromethyl)benzene (0.12 g, 0.67 mmol) were dissolved in DMF (1.0 mL) and Cs2CO3 (0.29 g, 0.89 mmol) was added. The reaction mixture was heated to 80° C. overnight. The solution was then diluted with ether and washed with water. The aqueous layer was back extracted with additional ether. The combined organic portions were washed with brine, dried over MgSO4 and concentrated under reduced pressure to give the title compound.

Workup

  1. washwashed with water
  2. extractionThe aqueous layer was back extracted with additional ether
  3. washThe combined organic portions were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f521f853eeaf48dcb9b1dcfb4838eec1
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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