1H-1,2,4-Triazole → 3-[1,2,4]Triazol-1-yl-pyridine-2-carbonitrile

HRID 857719Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 857719
[C:1]([C:3]1[C:8](F)=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].C(=O)([O-])[O-].[Cs+].[Cs+].[NH:16]1[CH:20]=[N:19][CH:18]=[N:17]1>CN(C=O)C.O>[N:16]1([C:8]2[C:3]([C:1]#[N:2])=[N:4][CH:5]=[CH:6][CH:7]=2)[CH:20]=[N:19][CH:18]=[N:17]1

Komponenten

6

Edukt 3

HCID 92571H-1,2,4-TriazoleHCID 10796Cesium carbonateHCID 70604082-Cyano-3-fluoropyridine

Produkt 1

HCID 218663013-[1,2,4]Triazol-1-yl-pyridine-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of 2-cyano-3-fluoro-pyridine (2.99 g, 24.49 mmol, preparation described in case 20443, filed Jun. 4, 1999) in DMF (30 ml) is added cesium carbonate (2.03 g, 29.39 mmol) and 1,2,4-triazole (2.03 g, 29.39 mmol) and the reaction mixture is stirred at 65° C. for 4 h. After cooling to room temperature, the mixture is diluted with water and extracted with EtOAc 3 times. The aqueous layer is saturated with LiCl and further extracted with EtOAc. The combined organic layer is dried on sodium sulfate, concentrated in vacuo. The crude product is purified by flash chromatography (silica gel, 2% MeOH containing 10% NH4OH in CH2Cl2 to 6%) to give 3-[1,2,4]Triazol-1-yl-pyridine-2-carbonitrile. 1H NMR (CDCl3, 400 MHz) δ 8.95 (s, 1H); 8.8 (d, J=4 Hz, 1 H); 8.24 (s, 1H); 8.22 (d, J=8.5 Hz, 1 H); 7.75 (dd, J=4, 8.5 Hz, 1 H).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc 3 times
  3. extractionfurther extracted with EtOAc
  4. customThe combined organic layer is dried on sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by flash chromatography (silica gel, 2% MeOH containing 10% NH4OH in CH2Cl2 to 6%)

Quellen und Nachweise

ORD-Eintrag
ord-f2e2dbc6b08e4a5c8d0bf356ec0363d6
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144899B2

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