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

  • CAS No. 876343-82-7

  • Cat. No. CS-D0707
  • Purity≥96%
  • MDL No.MFCD11046240

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

5-Bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine|CS-D0707

Structure of 876343-82-7

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General Information

  • CAS No. 876343-82-7
  • Cat. No. CS-D0707
  • Purity ≥96%
  • MDL No. MFCD11046240
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄BrClN₂
  • Molecular Weight 231.48
  • Synonym(s) 5-Brom-4-chlor-1H-pyrrolo[2,3-b]pyridin
  • SMILES ClC1=C2C(NC=C2)=NC=C1Br

Description

5-Bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine features a fused bicyclic core with complementary halogen substituents enabling direct functionalization in cross-coupling reactions. The electron-deficient pyrrolopyridine scaffold supports efficient C–H activation and transition metal catalysis. This bench-stable heterocycle serves as a key intermediate for pharmaceutical and agrochemical synthesis.

Application

5-Bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine serves as a versatile heterocyclic building block for the synthesis of biologically active compounds. Its complementary halogenation pattern enables sequential cross-coupling reactions under palladium catalysis, facilitating efficient construction of complex scaffolds. The molecule exhibits excellent bench stability and compatibility with standard reaction conditions, simplifying purification and scale-up. Functions effectively in Suzuki-Miyaura, Stille, and Negishi coupling protocols for medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • 5-Bromo-4-chloro-1-(triisopropylsilanyl)-7-azaindole|CS-W000380
      685513-96-6
    • ~87%
    • In-stock
      5-Bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine|CS-D0707
      876343-82-7

    References

    • ARRAY BIOPHARMA INC. Patent: WO2009/89352 A1, 2009 ; Location in patent: Page/Page column 59 ; WO 2009/089352 A1
  • Route2

    References

    • ChemMedChem, , vol. 9, # 2 p. 277 - 281
  • Route3

    References

    • ChemMedChem, , vol. 9, # 2 p. 277 - 281

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   2.9788
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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