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Methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate

  • CAS No. 916325-84-3

  • Cat. No. CS-0049002
  • Purity≥98%
  • MDL No.None

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

Methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate|CS-0049002

Structure of 916325-84-3

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General Information

  • CAS No. 916325-84-3
  • Cat. No. CS-0049002
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆BrN₃O₂
  • Molecular Weight 256.06
  • Synonym(s) None
  • SMILES COC(=O)C1=NNC2=NC=C(Br)C=C12

Description

Methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate features a brominated pyrazolopyridine core with a methyl ester at the 3-position, enabling direct incorporation into Suzuki-Miyaura and Buchwald-Hartwig coupling reactions. The electron-deficient heterocycle facilitates palladium-catalyzed transformations, while the bench-stable ester group supports straightforward derivatization in medicinal chemistry campaigns.

Application

Methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate serves as a versatile building block for constructing pyrazolopyridine-based scaffolds in medicinal chemistry. The bromo group enables palladium-catalyzed cross-coupling reactions, while the ester functionality supports further derivatization. Its bench-stable nature and compatibility with standard synthetic protocols facilitate efficient access to diverse heterocyclic architectures relevant to drug discovery.

Synthesis

  • Route1

    References

    • JANSSEN PHARMACEUTICA, N.V. Patent: WO2006/130673 A1, 2006 ; Location in patent: Page/Page column 74 ; WO 2006/130673 A1
  • Route2
    • null|null
      67-56-1
    • In-stock
      5-Bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid|CS-0037491
      916325-85-4
    • ~%
    • In-stock
      Methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate|CS-0049002
      916325-84-3

    References

    • US2013/296302 A1, ; Paragraph 0508 ;
  • Route3

    References

    • WO2011/84486 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-H320-H335
Precautionary Statements : P261-P280-P302+P352

Quality Control

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Computational Chemistry Data

  • TPSA   67.87
  • LogP   1.507
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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