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

  • CAS No. 799270-07-8

  • Cat. No. CS-0004744
  • Molecule weight222.04
  • Purity≥95%
  • MDL No.MFCD11046239

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

5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile|CS-0004744

Structure of 799270-07-8

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General Information

  • CAS No. 799270-07-8
  • Cat. No. CS-0004744
  • Purity ≥95%
  • MDL No. MFCD11046239
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₄BrN₃
  • Molecular Weight 222.04
  • Synonym(s) 5-BroMo-3-cyano-7-azaindole
  • SMILES N#CC1=CNC2=NC=C(Br)C=C21

Description

5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile features a fused heterocyclic core with dual electron-withdrawing groups: a bromine at the 5-position and a nitrile at the 3-position. This combination enhances electrophilicity for cross-coupling reactions while maintaining stability under standard conditions. The molecule serves as a key scaffold in medicinal chemistry for constructing bioactive compounds and functional materials.

Application

5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its compatible bromo and nitrile functionalities. The molecule exhibits excellent bench stability and facilitates efficient derivatization in late-stage functionalization workflows. Its rigid heterocyclic core supports integration into diverse API scaffolds, particularly in kinase inhibitor and CNS-targeted compound development.

Synthesis

  • Route1

    References

    • US2011/82138 A1, ; Page/Page column 69 ; US 20110082138 A1

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   52.47
  • LogP   2.19708
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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