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

HRID 892239Notes

Reaction equation

HRID 892239 reaction equation
[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

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 115356995-Bromo-2-hydrazinopyridine

Product 1

HCID 222368766-Bromo-3-cyclopropyl[1,2,4]triazolo[4,3-a]pyridineYield 106.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-bromo-pyridin-2-yl-hydrazine (15.0 g, 79.8 mmol) and cyclopropane carbonyl chloride (65 mL, 71.8 mmol) was heated at 90° C. for 18 hours. The brown mixture was allowed to cool to room temperature, filtered, and washed with toluene to afford a light brown solid. This solid was taken up in CHCl3, and washed with saturated aqueous NaHCO3. The organic layer was isolated, and the aqueous layer extracted with CHCl3 (2×). The combined organics were washed with brine, dried over magnesium sulfate, and concentrated in vacuo to give the title compound as a tan solid (18.2 g, 96%).

Workup

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

Sources & evidence

ORD record
ord-4318df9c902f48128a09e73a64a88f45
Source dataset
uspto-grants-2006_02
Patent number
US07005523B2

Reaction notes

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