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CS-W001157 4
Total: USD 88.00

4-Bromo-6-azaindole

  • CAS No. 69872-17-9

  • Cat. No. CS-W019705
  • Molecule weight197.03
  • Purity≥97%
  • MDL No.MFCD11847768

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

4-Bromo-6-azaindole|CS-W019705

Structure of 69872-17-9

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General Information

  • CAS No. 69872-17-9
  • Cat. No. CS-W019705
  • Purity ≥97%
  • MDL No. MFCD11847768
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅BrN₂
  • Molecular Weight 197.03
  • Synonym(s) 4-Bromo-1H-pyrrolo[2,3-c]pyridine; 4-Bromo-1H-pyrrolo[2,3-c]pyridine (69872-17-9)
  • SMILES BrC1=CN=CC2=C1C=CN2

Description

4-Bromo-6-azaindole is a heterocyclic building block featuring a bromine substituent at the 4-position and a nitrogen atom at the 6-position of the indole scaffold. This electron-deficient core enables direct functionalization in cross-coupling reactions, integrating seamlessly into pharmaceutical intermediates and advanced materials. The bromo group facilitates palladium-catalyzed transformations under standard conditions, while the azaindole framework enhances solubility and metabolic stability.

Application

4-Bromo-6-azaindole serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions for the construction of biaryl and heteroaryl scaffolds. The bromine substituent provides high reactivity in Suzuki, Stille, and Negishi couplings, while the 6-azaindole core offers enhanced solubility and hydrogen-bonding capacity. Its bench-stable nature and compatibility with diverse functional groups make it ideal for iterative synthesis in API development.

Synthesis

  • Route1
    • 2-(3-Bromo-5-nitro-4-pyridinyl)-N,N-dimethylethenamine|CS-0193056
      1258875-12-5
    • ~73%
    • In-stock
      4-Bromo-6-azaindole|CS-W019705
      69872-17-9

    References

    • PFIZER INC Patent: US2005/90529 A1, 2005 ; Location in patent: Page/Page column 82-83 ; US 20050090529 A1
  • Route2
    • null|null
      69872-16-8
    • ~81%
    • In-stock
      4-Bromo-6-azaindole|CS-W019705
      69872-17-9

    References

    • Chekler, Eugene L. Piatnitski; Unwalla, Rayomond; Khan, Taukeer A.; Tangirala, Raghuram S.; Johnson, Mark; St. Andre, Michael; Anderson, James T.; Kenney, Thomas; Chiparri, Sue; McNally, Chris; Kilbourne, Edward; Thompson, Catherine; Nagpal, Sunil; Weber, Gregory; Schelling, Scott; Owens, Jane; Morris, Carl A.; Powell, Dennis; Verhoest, Patrick R.; Gilbert, Adam M. Journal of Medicinal Chemistry, 2014 , vol. 57, # 6 p. 2462 - 2471
  • Route3

    References

    • Tetrahedron Letters, , vol. 53, # 4 p. 377 - 379

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

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Computational Chemistry Data

  • TPSA   28.68
  • LogP   2.3254
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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