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CS-W001157 4
Total: USD 88.00

Ethyl imidazo[1,5-a]pyridine-3-carboxylate

  • CAS No. 81803-60-3

  • Cat. No. CS-W022717
  • Purity≥98%
  • MDL No.MFCD10697855

*For research and further manufacturing use only, not for direct human use.

Ethyl imidazo[1,5-a]pyridine-3-carboxylate|CS-W022717

Structure of 81803-60-3

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General Information

  • CAS No. 81803-60-3
  • Cat. No. CS-W022717
  • Purity ≥98%
  • MDL No. MFCD10697855
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₀N₂O₂
  • Molecular Weight 190.20
  • Synonym(s) Imidazo[1,5-a]pyridine-3-carboxylic acid ethyl ester
  • SMILES O=C(C1=NC=C2C=CC=CN21)OCC

Description

Ethyl imidazo[1,5-a]pyridine-3-carboxylate features a rigid, electron-deficient heterocyclic core that integrates seamlessly into medicinal chemistry scaffolds. This bench-stable ester delivers enhanced metabolic resilience and facilitates efficient derivatization in late-stage functionalization workflows.

Application

Ethyl imidazo[1,5-a]pyridine-3-carboxylate serves as a versatile heterocyclic building block for the synthesis of biologically active compounds. Its imidazopyridine core exhibits favorable stability and compatibility with standard synthetic transformations. The ester functionality enables facile derivatization via hydrolysis, reduction, or coupling reactions, supporting diverse functional group manipulations. This scaffold is particularly valuable in medicinal chemistry for constructing kinase inhibitors and other targeted therapeutics.

Synthesis

  • Route1
    • null|null
      46460-25-7
    • ~42%
    • In-stock
      Ethyl imidazo[1,5-a]pyridine-3-carboxylate|CS-W022717
      81803-60-3

    References

    • MERCK and CO., INC. Patent: WO2008/85302 A1, 2008 ; Location in patent: Page/Page column 96 ; WO 2008/085302 A1
  • Route2
    • In-stock
      2-(Aminomethyl)pyridine|CS-W007488
      3731-51-9
    • null|null
      4755-77-5
    • ~97%
    • In-stock
      Ethyl imidazo[1,5-a]pyridine-3-carboxylate|CS-W022717
      81803-60-3

    References

    • Trotter, B. Wesley; Nanda, Kausik K.; Burgey, Christopher S.; Potteiger, Craig M.; Deng, James Z.; Green, Ahren I.; Hartnett, John C.; Kett, Nathan R.; Wu, Zhicai; Henze, Darrell A.; Penna, Kimberly Della; Desai, Reshma; Leitl, Michael D.; Lemaire, Wei; White, Rebecca B.; Yeh, Suzie; Urban, Mark O.; Kane, Stefanie A.; Hartman, George D.; Bilodeau, Mark T. Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 8 p. 2354 - 2358
  • Route3

    References

    • Pelletier, Guillaume; Charette, Andre B. Organic Letters, 2013 , vol. 15, # 9 p. 2290 - 2293

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   43.6
  • LogP   1.511
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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