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CS-W001157 4
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3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

  • CAS No. 945256-29-1

  • Cat. No. CS-0002345
  • Purity≥97%
  • MDL No.MFCD11616359

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

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine|CS-0002345

Structure of 945256-29-1

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General Information

  • CAS No. 945256-29-1
  • Cat. No. CS-0002345
  • Purity ≥97%
  • MDL No. MFCD11616359
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₇BN₂O₂
  • Molecular Weight 244.10
  • Synonym(s) 7-Azaindole-3-Boronic Acid Pinacol Ester
  • SMILES CC1(C)OB(OC(C)1C)C2=CNC3=NC=CC=C23

Description

This boronate-functionalized pyrrolopyridine integrates readily into Suzuki-Miyaura coupling reactions under standard conditions. The tetramethylborolane moiety ensures high stability and compatibility with diverse reaction environments, enabling efficient C–C bond formation in synthetic sequences.

Application

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine serves as a versatile boronate building block for palladium-catalyzed cross-coupling reactions. Its pyrrolo[2,3-b]pyridine core provides a rigid, electron-deficient heterocyclic scaffold commonly found in bioactive molecules. The pinacol boronate group enables excellent bench stability, facile purification, and compatibility with diverse reaction conditions, facilitating efficient construction of complex scaffolds in medicinal chemistry and materials science.

Synthesis

  • Route1
    • In-stock
      7-Azaindole|CS-B0516
      271-63-6
    • null|null
      25015-63-8
    • ~77%
    • In-stock
      3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine|CS-0002345
      945256-29-1

    References

    • Preshlock, Sean M.; Plattner, Donald L.; Maligres, Peter E.; Krska, Shane W.; Maleczka Jr., Robert E.; Smith III, Milton R. Angewandte Chemie - International Edition, 2013 , vol. 52, # 49 p. 12915 - 12919 Angew. Chem., 2013 , vol. 125, # 49 p. 13153 - 13157,5
  • Route2

    References

    • Larsen, Matthew A.; Hartwig, John F. Journal of the American Chemical Society, 2014 , vol. 136, # 11 p. 4287 - 4299
  • Route3

    References

    • Larsen, Matthew A.; Hartwig, John F. Journal of the American Chemical Society, 2014 , vol. 136, # 11 p. 4287 - 4299

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   47.14
  • LogP   1.8621
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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