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

HRID 2198128Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2198128
[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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8b7571f0c4e843cd91290cb319291d10
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338610B2

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