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

  • CAS No. 866546-09-0

  • Cat. No. CS-0004723
  • Purity≥97%
  • MDL No.MFCD11100204

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

3-Bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine|CS-0004723

Structure of 866546-09-0

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General Information

  • CAS No. 866546-09-0
  • Cat. No. CS-0004723
  • Purity ≥97%
  • MDL No. MFCD11100204
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄BrClN₂
  • Molecular Weight 231.48
  • Synonym(s) 3-Bromo-5-chloro-7-azaindole
  • SMILES BrC1=CNC2=NC=C(Cl)C=C21

Description

3-Bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine is a heteroaryl halide featuring complementary electrophilic sites for cross-coupling. The bromo group enables palladium-catalyzed reactions, while the chloro substituent offers orthogonal reactivity under selective conditions. This scaffold integrates readily into complex molecular architectures through modular transformations.

Application

3-Bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine serves as a versatile heterocyclic building block for the synthesis of pharmaceutical intermediates and functional materials. Its complementary halogenation pattern enables selective metal-catalyzed cross-coupling reactions, including Suzuki-Miyaura and Stille couplings, with excellent functional group tolerance. The molecule exhibits good bench stability and facilitates efficient purification, making it well-suited for iterative synthetic sequences in medicinal chemistry and process development.

Synthesis

  • Route1

    References

    • ALZHEIMER'S INSTITUTE OF AMERICA, INC.; SEBAHAR, Paul R.; HALTER, Robert J.; MCLEOD, Donald A.; PARKER, Daniel P.; YAGER, Kraig M.; SHENDEROVICH, Mark D.; HOLCOMB, Ryan C.; RICHARDS, Burt; BARTEL, Paul L.; KIM, Se-Ho; SLATTUM, Paul M.; TANGALLAPALLY, Rajendra; TROVATO, Richard; YUNGAI, Ashantai J. Patent: WO2014/4863 A2, 2014 ; Location in patent: Paragraph 0230 ;
  • Route2

    References

    • WO2011/137022 A1, ;
  • Route3

    References

    • WO2011/137022 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   28.68
  • LogP   2.9788
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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