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

HRID 854432Notes

Reaction equation

HRID 854432 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 (65.0 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%).

Workup

  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

Sources & evidence

ORD record
ord-c54c353e6d42405cb01cd9378b56e6e0
Source dataset
uspto-grants-2007_08
Patent number
US07259171B2

Reaction notes

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