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CS-W001157 4
Total: USD 88.00

2-Bromo-5H-pyrrolo[2,3-b]pyrazine

  • CAS No. 875781-43-4

  • Cat. No. CS-W008866
  • Purity≥98%
  • MDL No.MFCD09834822

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

2-Bromo-5H-pyrrolo[2,3-b]pyrazine|CS-W008866

Structure of 875781-43-4

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General Information

  • CAS No. 875781-43-4
  • Cat. No. CS-W008866
  • Purity ≥98%
  • MDL No. MFCD09834822
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₄BrN₃
  • Molecular Weight 198.02
  • Synonym(s) 2-Bromo-5H-pyrrolo[2,3-b]pyrazine; 5-Bromo-4,7-diazaindole; 2-bromo-5H-pyrrolo[3,2-b]pyrazine
  • SMILES BrC1=CN=C(NC=C2)C2=N1

Description

2-Bromo-5H-pyrrolo[2,3-b]pyrazine is a heterocyclic bromide featuring a fused pyrrole-pyrazine core, offering a rigid, electron-deficient scaffold. This structure enables direct functionalization in cross-coupling reactions, integrating readily into complex molecular architectures. The bromine atom serves as a high-reactivity handle for palladium-catalyzed transformations, facilitating efficient access to diversified nitrogen-rich frameworks under standard conditions.

Application

2-Bromo-5H-pyrrolo[2,3-b]pyrazine serves as a versatile heterocyclic building block for the synthesis of advanced pharmaceutical intermediates. Its bromine substituent enables efficient palladium-catalyzed cross-coupling reactions, including Suzuki and Buchwald-Hartwig aminations, facilitating rapid access to functionalized pyrrolopyrazine scaffolds. The compound exhibits good bench stability and compatibility with common protecting groups, supporting its use in multi-step synthetic sequences for targeted API development.

Synthesis

  • Route1
    • null|null
      875781-42-3
    • ~42%
    • In-stock
      2-Bromo-5H-pyrrolo[2,3-b]pyrazine|CS-W008866
      875781-43-4

    References

    • WO2006/15124 A2, ; Page/Page column 102-103 ; WO 2006/015124 A2
  • Route2
    • null|null
      1416740-15-2
    • ~70%
    • In-stock
      2-Bromo-5H-pyrrolo[2,3-b]pyrazine|CS-W008866
      875781-43-4

    References

    • WO2012/178123 A1, ; Page/Page column 63-64 ; WO 2012/178123 A1
  • Route3

    References

    • WO2011/149950 A2, ; WO 2011/149950 A2

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   41.57
  • LogP   1.7204
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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