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

HRID 1795268Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1795268
[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 Sakamoto et. al., Chem. Pharm. Bull. 1985, 33(2), 565–571) 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, 1H); 8.24 (s, 1H); 8.22 (d, J=8.5 Hz, 1H); 7.75 (dd, J=4, 8.5 Hz, 1H).

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-a5686d635e1f4e9f905ae2316ac9d293
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07026324B2

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