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CS-W001157 4
Total: USD 88.00

Methyl imidazo[1,2-a]pyridine-6-carboxylate

  • CAS No. 136117-69-6

  • Cat. No. CS-0048890
  • Purity≥97%
  • MDL No.None

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

Methyl imidazo[1,2-a]pyridine-6-carboxylate|CS-0048890

Structure of 136117-69-6

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General Information

  • CAS No. 136117-69-6
  • Cat. No. CS-0048890
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₈N₂O₂
  • Molecular Weight 176.17
  • Synonym(s) Imidazo[1,2-a]pyridine-6-carboxylic acid, methyl ester
  • SMILES COC(=O)C1=CN2C=CN=C2C=C1

Description

Methyl imidazo[1,2-a]pyridine-6-carboxylate is a heterocyclic ester featuring a fused imidazo[1,2-a]pyridine core with a methyl carboxylate handle at the 6-position. This scaffold integrates electron-rich aromaticity with a reactive ester group, enabling direct incorporation into synthetic sequences. The compound exhibits bench-stable handling and compatibility with standard coupling conditions, facilitating efficient access to advanced intermediates in medicinal chemistry and materials synthesis.

Application

Methyl imidazo[1,2-a]pyridine-6-carboxylate serves as a versatile heterocyclic building block for medicinal chemistry and catalysis research. Its fused imidazopyridine core exhibits enhanced metabolic stability and π-stacking potential, while the ester group enables straightforward functionalization via hydrolysis, reduction, or coupling reactions. The compound demonstrates excellent bench stability and compatibility with common reaction conditions, facilitating efficient access to complex scaffolds in drug discovery campaigns.

Synthesis

  • Route1

    References

    • METHYLGENE, INC. Patent: WO2005/30704 A1, 2005 ; Location in patent: Page/Page column 247 ;
  • Route2
    • null|null
      107-20-0
    • In-stock
      methyl 6-aminonicotinate|CS-W002681
      36052-24-1
    • ~80%
    • In-stock
      Methyl imidazo[1,2-a]pyridine-6-carboxylate|CS-0048890
      136117-69-6

    References

    • Hughes, Samantha J.; Millan, David S.; Kilty, Iain C.; Lewthwaite, Russell A.; Mathias, John P.; Reilly, Mark A.O.; Pannifer, Andrew; Phelan, Anne; Stuehmeier, Frank; Baldock, Darren A.; Brown, David G. Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 21 p. 6586 - 6590
  • Route3
    • In-stock
      Imidazo[1,2-a]pyridine-6-carboxylic acid|CS-W005545
      139022-25-6
    • null|null
      74-88-4
    • ~39%
    • In-stock
      Methyl imidazo[1,2-a]pyridine-6-carboxylate|CS-0048890
      136117-69-6

    References

    • Gardinier, Kevin M.; Gernert, Douglas J.; Grese, Timothy A.; Neel, David A.; Mapes, Christopher M.; Michellys, Pierre-Yves; Boehm, Marcus F. Patent: US2004/167160 A1, 2004 ;

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   1.1209
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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