Cyclopropanecarbonyl chloride → 6-Bromo-3-cyclopropyl[1,2,4]triazolo[4,3-a]pyridine

HRID 1743989Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1743989
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[CH:10]1([C:13](Cl)=O)[CH2:12][CH2:11]1>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:13]([CH:10]3[CH2:12][CH2:11]3)=[N:9][N:8]=2)[CH:7]=1

Komponenten

4

Edukt 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 115356995-Bromo-2-hydrazinopyridine

Produkt 1

HCID 222368766-Bromo-3-cyclopropyl[1,2,4]triazolo[4,3-a]pyridineAusbeute 106,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 5-bromo-pyridin-2-yl-hydrazine (15.0 g, 79.8 mmol) and cyclopropane carbonyl chloride (65.0 mL, 71.8 mmol) is heated at 90° C. for 18 hours. The brown mixture is allowed to cool to room temperature, filtered, and washed with toluene to afford a light brown solid. This solid is taken up in chloroform (CHCl3), and washed with saturated NaHCO3. The organic layer is isolated, and the aqueous layer extracted twice with chloroform (CHCl3). The combined organics are washed with brine, dried over magnesium sulfate, and concentrated in vacuo to give the title compound as a tan solid (18.2 g, 96%).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. washwashed with toluene
  4. customto afford a light brown solid
  5. washwashed with saturated NaHCO3
  6. customThe organic layer is isolated
  7. extractionthe aqueous layer extracted twice with chloroform (CHCl3)
  8. washThe combined organics are washed with brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cf35e6820a8b4cf385666f4ade8cc9d0
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07012143B2

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