Water → 3-fluoro-2-(4-methoxy-3-(4-(morpholin-4-yl)phenyl)-1H-pyrazolo[4,3-c]pyridin-1-yl)benzonitrile

HRID 2206245Notes

Reaction equation

HRID 2206245 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[C:9]([C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[CH:14][CH:13]=3)=[N:10][NH:11][C:7]=2[CH:6]=[CH:5][N:4]=1.F[C:25]1[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:26]=1[C:27]#[N:28].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:33][C:32]1[C:25]([N:11]2[C:7]3[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[C:8]=3[C:9]([C:12]3[CH:13]=[CH:14][C:15]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[CH:16][CH:17]=3)=[N:10]2)=[C:26]([CH:29]=[CH:30][CH:31]=1)[C:27]#[N:28]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 889352,3-DifluorobenzonitrileHCID 1179878324-methoxy-3-[4-(4-morpholinyl)phenyl]-1H-Pyrazolo[4,3-c]pyridine

Product 1

HCID 1179884943-fluoro-2-(4-methoxy-3-(4-(morpholin-4-yl)phenyl)-1H-pyrazolo[4,3-c]pyridin-1-yl)benzonitrileYield 77.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-methoxy-3-(4-(morpholin-4-yl)phenyl)-1H-pyrazolo[4,3-c]pyridine (355 mg), 2,3-difluorobenzonitrile (180 mg) and potassium carbonate in DMF (5 mL) was stirred at 100° C. for 2.5 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting solid was washed with petroleum ether to give the title compound (380 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe resulting solid was washed with petroleum ether

Sources & evidence

ORD record
ord-2fba54ed8ece4c31811c133d41824da7
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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