2-Bromo-7-fluoro-[1,2,4]triazolo[1,5-a]pyridine
[CAS# 2090398-13-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound
• Name: 2-Bromo-7-fluoro-[1,2,4]triazolo[1,5-a]pyridine
• Molecular Formula: C₆H₃BrFN₃
• Molecular Weight: 216.01
• CAS Registry Number: 2090398-13-1
• SMILES: C1=CN2C(=NC(=N2)Br)C=C1F

Properties

• Density: 2.0±0.1 g/cm³ Calc.^*
• Index of refraction: 1.721 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovery and Applications

2-Bromo-7-fluoro-[1,2,4]triazolo[1,5-a]pyridine is a fused heterocyclic compound that combines a pyridine ring with a 1,2,4-triazole moiety. The bromine atom at position 2 and the fluorine at position 7 provide reactive handles for further functionalization, making this scaffold useful for medicinal chemistry and agrochemical applications.

The triazolo[1,5-a]pyridine core is planar and electron-rich, enabling π–π stacking and hydrogen bonding interactions when binding to biological targets. This makes it a potential scaffold for kinase inhibitors, antiviral agents, and other enzyme modulators. The bromine atom allows cross-coupling reactions, such as Suzuki or Buchwald–Hartwig coupling, to introduce diverse substituents, while the fluorine atom can enhance metabolic stability, lipophilicity, and binding affinity.

Synthetic routes typically start from appropriately substituted pyridine precursors. Cyclization with hydrazine or substituted triazoles forms the fused triazolo ring, followed by selective halogenation to install the bromine and fluorine atoms. Careful control of reaction conditions ensures regioselectivity, particularly for the 2- and 7-positions.

In drug discovery, derivatives of 2-bromo-7-fluoro-[1,2,4]triazolo[1,5-a]pyridine have been investigated as kinase modulators, antiviral leads, and as intermediates in more complex heterocyclic libraries. The combination of a halogenated fused heterocycle allows fine-tuning of pharmacokinetic and pharmacodynamic properties.

References

CN-118561872-A (2023) Pyrimidopyridine biological inhibitor, preparation method and application thereof. Link

WO-2024178304-A1 (2023) KRAS modulators and preparation methods thereof. Link

TW-202430184-A (2022) Crystalline form of KRAS G12D inhibitors and preparation method thereof. Link