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CS-W001157 4
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5-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine

  • CAS No. 183208-22-2

  • Cat. No. CS-0043009
  • Purity≥97%
  • MDL No.MFCD14706089

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

5-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine|CS-0043009

Structure of 183208-22-2

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General Information

  • CAS No. 183208-22-2
  • Cat. No. CS-0043009
  • Purity ≥97%
  • MDL No. MFCD14706089
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇BrN₂
  • Molecular Weight 211.06
  • Synonym(s) 5-BroMo-1-Methylpyrrolo[2,3-b]pyridine
  • SMILES CN1C=CC2=CC(Br)=CN=C12

Description

5-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine features a brominated pyrrolopyridine core with a methyl group at the nitrogen, enabling direct functionalization in cross-coupling reactions. The electron-deficient heterocycle integrates efficiently into complex scaffolds, offering high reactivity under standard conditions with minimal decomposition. This bench-stable compound serves as a key building block for pharmaceutical intermediates and advanced materials.

Application

5-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine serves as a versatile building block for the synthesis of biologically active heterocycles, enabling palladium-catalyzed cross-coupling reactions with broad functional group tolerance. The bromo group facilitates Suzuki, Stille, and Negishi couplings, while the methylated pyrrolopyridine core provides structural rigidity and enhanced metabolic stability. This compound exhibits excellent bench stability and simplifies purification, making it well-suited for medicinal chemistry campaigns and process development in API synthesis.

Synthesis

  • Route1
    • In-stock
      5-Bromo-7-azaindole|CS-B0096
      183208-35-7
    • null|null
      74-88-4
    • ~64%
    • In-stock
      5-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine|CS-0043009
      183208-22-2

    References

    • Guillard, Jerome; Larraya, Carlos; Viaud-Massuard, Marie-Claude Heterocycles, 2003 , vol. 60, # 4 p. 865 - 877
  • Route2

    References

    • Guillard, Jerome; Larraya, Carlos; Viaud-Massuard, Marie-Claude Heterocycles, 2003 , vol. 60, # 4 p. 865 - 877
  • Route3

    References

    • Guillard, Jerome; Larraya, Carlos; Viaud-Massuard, Marie-Claude Heterocycles, 2003 , vol. 60, # 4 p. 865 - 877

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   17.82
  • LogP   2.3358
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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