Water → 4-(1-(2,2-difluoroethyl)-1H-pyrazolo[4,3-b]pyridin-3-yl)phenol

HRID 573351Notes

Reaction equation

HRID 573351 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19]3=[N:20][CH:21]=[CH:22][CH:23]=[C:18]3[NH:17][N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].FC(F)(F)S(O[CH2:36][CH:37]([F:39])[F:38])(=O)=O.O>CN(C=O)C>[F:38][CH:37]([F:39])[CH2:36][N:17]1[C:18]2[C:19](=[N:20][CH:21]=[CH:22][CH:23]=2)[C:15]([C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)=[N:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27740892,2-Difluoroethyl trifluoromethanesulfonateHCID 866889913-[4-(Benzyloxy)phenyl]-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 1364090914-(1-(2,2-difluoroethyl)-1H-pyrazolo[4,3-b]pyridin-3-yl)phenolYield 51.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 3-[4-(benzyloxy)phenyl]-1H-pyrazolo[4,3-b]pyridine (300 mg) and Cs2CO3 (649 mg) in DMF (4 ml) was added 2,2-difluoroethyl trifluoromethanesulfonate (234 mg) at 0° C. The mixture was stirred at room temperature for 12 h, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was dissolved in EtOH (8 mL) and 10% Pd—C (200 mg) was added. The mixture was stirred at room temperature for 30 min under H2 atmosphere, filtered and evaporated. The residue was purified by silica gel column chromatography (hexane/AcOEt) to give the title compound (142 mg).

Workup

  1. extractionextracted with AcOEt
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in EtOH (8 mL)
  5. addition10% Pd—C (200 mg) was added
  6. stirringThe mixture was stirred at room temperature for 30 min under H2 atmosphere
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by silica gel column chromatography (hexane/AcOEt)

Sources & evidence

ORD record
ord-2d93f91c60a54f20900506bdedc76ff6
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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