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Methyl 4-chloro-7-azaindole-5-carboxylate

  • CAS No. 951625-93-7

  • Cat. No. CS-B0807
  • Purity≥95%
  • MDL No.MFCD09755979

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

Methyl 4-chloro-7-azaindole-5-carboxylate|CS-B0807

Structure of 951625-93-7

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General Information

  • CAS No. 951625-93-7
  • Cat. No. CS-B0807
  • Purity ≥95%
  • MDL No. MFCD09755979
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₇ClN₂O₂
  • Molecular Weight 210.62
  • Synonym(s) None
  • SMILES O=C(C1=CN=C(NC=C2)C2=C1Cl)OC

Description

Methyl 4-chloro-7-azaindole-5-carboxylate features a sterically hindered, electron-deficient azaindole core paired with a reactive ester handle. This combination enables direct coupling in late-stage functionalization workflows. The molecule exhibits enhanced stability under standard conditions and facilitates efficient incorporation into complex heterocyclic architectures.

Application

Methyl 4-chloro-7-azaindole-5-carboxylate serves as a versatile building block for heterocyclic synthesis, enabling direct functionalization at the C4 position via palladium-catalyzed cross-coupling reactions. Its chloro group exhibits high reactivity in Suzuki, Stille, and Negishi transformations, while the methyl ester facilitates downstream derivatization. The 7-azaindole core provides enhanced solubility and metabolic stability, making it valuable for medicinal chemistry applications. Bench-stable and amenable to standard purification methods, it functions efficiently in multi-step synthetic sequences.

Synthesis

  • Route1
    • null|null
      67-56-1
    • In-stock
      4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid|CS-M2751
      920966-03-6
    • ~%
    • In-stock
      Methyl 4-chloro-7-azaindole-5-carboxylate|CS-B0807
      951625-93-7

    References

    • Helicon Therapeutics, Inc. Patent: US2012/95016 A1, 2012 ; Location in patent: Page/Page column 24 ;
  • Route2

    References

    • BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian, T.; SCOTT, Daniel; CONLON, Patrick; JENKINS, Tracy, J.; POWELL, Noel; GUAN, Bing; CURERVO, Julio, H.; WANG, Deping; TAVERAS, Art Patent: WO2012/58645 A1, 2012 ; WO 2012/058645 A1

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   54.98
  • LogP   2.0029
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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