Triethylamine → 1-(4-fluorophenyl)-1H-pyrazolo[4,3-c]pyridine-4-carbonitrile

HRID 559659Notes

Reaction equation

HRID 559659 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH:15]=[CH:14][N+:13]([O-])=[CH:12][C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.C[Si]([C:22]#[N:23])(C)C.CCN(CC)CC>C(#N)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH:15]=[CH:14][N:13]=[C:12]([C:22]#[N:23])[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 580842441-(4-fluorophenyl)-1H-pyrazolo[4,3-c]pyridine 5-oxide

Product 1

HCID 592785181-(4-fluorophenyl)-1H-pyrazolo[4,3-c]pyridine-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-1H-pyrazolo[4,3-c]pyridine 5-oxide (0.300 g, 1.31 mmol) in acetonitrile (10 mL) was added trimethylsilyl cyanide (TMSCN) (931 μL, 6.99 mmol) followed by Et3N (0.930 mL, 6.69 mmol) and the mixture was warmed at reflux. After 3 hours, the mixture was diluted with water and the solid collected by filtration washing with water. The flakey solid was then dissolved in methanol and concentrated to afford 1-(4-fluorophenyl)-1H-pyrazolo[4,3-c]pyridine-4-carbonitrile.

Workup

  1. temperaturethe mixture was warmed
  2. temperatureat reflux
  3. filtrationthe solid collected by filtration
  4. washwashing with water
  5. dissolutionThe flakey solid was then dissolved in methanol
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cd62d2fafdfe4081bf3eb03a6609e2d2
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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