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CS-W001157 4
Total: USD 88.00

5-Bromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one

  • CAS No. 183208-34-6

  • Cat. No. CS-B0502
  • Purity≥95%
  • MDL No.MFCD07367221

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

5-Bromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one|CS-B0502

Structure of 183208-34-6

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General Information

  • CAS No. 183208-34-6
  • Cat. No. CS-B0502
  • Purity ≥95%
  • MDL No. MFCD07367221
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅BrN₂O
  • Molecular Weight 213.03
  • Synonym(s) 5-Bromo-7-Aza-Indolin-2(3h)-One
  • SMILES O=C(C1)NC(C1=C2)=NC=C2Br

Description

5-Bromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one features a fused heterocyclic core with a bromo substituent at the 5-position, enabling direct functionalization in cross-coupling reactions. The lactam moiety imparts stability and polarity, facilitating solubility in common organic solvents. This scaffold serves as a key building block for medicinal chemistry applications, particularly in kinase inhibitor development and macrocyclic peptide synthesis.

Application

5-Bromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one serves as a versatile building block for constructing bioactive heterocycles, enabling palladium-catalyzed cross-coupling reactions due to its stable bromine handle. The pyrrolopyridinone core exhibits favorable functional group tolerance and bench stability, facilitating downstream modifications in medicinal chemistry and process development workflows.

Synthesis

  • Route1
    • null|null
      183208-32-4
    • ~92%
    • In-stock
      5-Bromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one|CS-B0502
      183208-34-6

    References

    • Journal of the American Chemical Society, , vol. 128, # 45 p. 14426 - 14427
  • Route2
    • 3,3,5-Tribromoindolin-2-one|CS-0596187
      92635-29-5
    • ~73%
    • In-stock
      5-Bromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one|CS-B0502
      183208-34-6

    References

    • US6350747 B1, ; Page column 69 ;
  • Route3
    • 3,3-Dibromo-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one|CS-0329581
      113423-51-1
    • ~%
    • In-stock
      5-Bromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one|CS-B0502
      183208-34-6

    References

    • US6369086 B1, ; US 6369086 B1

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   41.99
  • LogP   1.3387
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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