3-Bromo-[1,2,4]triazolo[4,3-a]pyridine Chemical Properties

Melting point:

165-167 °C

Density 

1.89±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

0.97±0.50(Predicted)

Appearance

Light brown to brown Solid

InChI

InChI=1S/C6H4BrN3/c7-6-9-8-5-3-1-2-4-10(5)6/h1-4H

InChIKey

BOKHADJFZUWNSH-UHFFFAOYSA-N

SMILES

C12=NN=C(Br)N1C=CC=C2

Safety Information

HS Code 

2933998090

3-Bromo-[1,2,4]triazolo[4,3-a]pyridine Usage And Synthesis

Uses

3-Bromo-[1,2,4]triazolo[4,3-a]pyridine is an intermediate used to prepare bi-aryl amines as mGluR5 modulators for treating gastrointestinal, urinary tract, and nervous system disorders.

Synthesis

General procedure for the synthesis of 3-bromo-[1,2,4]triazolo[4,3-a]pyridine from [1,2,4]triazolo[4,3-a]pyridine: [1,2,4]triazolo[4,3-a]pyridine (1.26 g) and N-bromosuccinimide (NBS, 1.98 g) were dissolved in chloroform, and the reaction was carried out at reflux for 5 h followed by a 14-h stand at room temperature. Upon completion of the reaction, saturated aqueous potassium carbonate (200 mL) and potassium hydroxide (20 g) were added to the mixture, and the organic layer was separated after sufficient shaking. The aqueous layer was extracted twice with dichloromethane (DCM). All organic layers were combined and dried over anhydrous sodium sulfate (Na2SO4) followed by evaporation of the solvent under vacuum to afford the target product 3-bromo-[1,2,4]triazolo[4,3-a]pyridine in 60% yield.

References

[1] Patent: EP2743266, 2014, A2. Location in patent: Page/Page column

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