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5-Bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridine

  • CAS No. 1172067-95-6

  • Cat. No. CS-0004477
  • Molecule weight215.02
  • Purity≥96%
  • MDL No.MFCD12031517

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

5-Bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridine|CS-0004477

Structure of 1172067-95-6

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General Information

  • CAS No. 1172067-95-6
  • Cat. No. CS-0004477
  • Purity ≥96%
  • MDL No. MFCD12031517
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄BrFN₂
  • Molecular Weight 215.02
  • Synonym(s) 5-BroMo-4-fluoro-7-azaindole
  • SMILES FC1=C2C(NC=C2)=NC=C1Br

Description

5-Bromo-4-fluoro-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 palladium-catalyzed transformations, while the bromo and fluoro groups offer orthogonal reactivity for sequential derivatization. This bench-stable heterocycle serves as a key building block in medicinal chemistry and materials science.

Application

5-Bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridine serves as a versatile building block in the synthesis of bioactive heterocycles, enabling palladium-catalyzed cross-coupling reactions due to its orthogonal halogen reactivity. The bromo and fluoro substituents facilitate sequential functionalization, while the pyrrolo[2,3-b]pyridine core offers structural rigidity and favorable electronic properties for pharmaceutical scaffold development. Its bench stability and compatibility with standard coupling conditions make it ideal for medicinal chemistry campaigns and process-scale applications.

Synthesis

  • Route1

    References

    • VERNALIS (RandD) LIMITED; STOKES, Stephen; GRAHAM, Christoper John; RAY, Stuart Christopher; STEFANIAK, Emma Jayne Patent: WO2013/114113 A1, 2013 ;
  • Route2

    References

    • VERNALIS (RandD) LIMITED; STOKES, Stephen; GRAHAM, Christoper John; RAY, Stuart Christopher; STEFANIAK, Emma Jayne Patent: WO2013/114113 A1, 2013 ;
  • Route3
    • 4-Fluoro-1-(triisopropylsilanyl)-7-azaindole|CS-B0521
      640735-25-7
    • ~%
    • In-stock
      5-Bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridine|CS-0004477
      1172067-95-6

    References

    • VERNALIS (RandD) LIMITED; STOKES, Stephen; GRAHAM, Christoper John; RAY, Stuart Christopher; STEFANIAK, Emma Jayne Patent: WO2013/114113 A1, 2013 ;

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   28.68
  • LogP   2.4645
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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