Cas no 1159982-08-7 (3-bromo-1h-pyrrolo[2,3-b]pyridine-4-carbaldehyde)

3-bromo-1h-pyrrolo[2,3-b]pyridine-4-carbaldehyde structure
1159982-08-7 structure
Product Name:3-bromo-1h-pyrrolo[2,3-b]pyridine-4-carbaldehyde
CAS No:1159982-08-7
MF:C8H5BrN2O
MW:225.042100667953
CID:1206008
PubChem ID:45790302
Update Time:2025-11-02

3-bromo-1h-pyrrolo[2,3-b]pyridine-4-carbaldehyde Chemical and Physical Properties

Names and Identifiers

    • 3-bromo-1h-pyrrolo[2,3-b]pyridine-4-carbaldehyde
    • DTXSID60672262
    • SB14458
    • 1159982-08-7
    • Inchi: 1S/C8H5BrN2O/c9-6-3-11-8-7(6)5(4-12)1-2-10-8/h1-4H,(H,10,11)
    • InChI Key: ZEMGCLLLXCWXPJ-UHFFFAOYSA-N
    • SMILES: BrC1=CNC2C1=C(C=O)C=CN=2

Computed Properties

  • Exact Mass: 223.95853g/mol
  • Monoisotopic Mass: 223.95853g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 188
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.5
  • Topological Polar Surface Area: 45.8?2

3-bromo-1h-pyrrolo[2,3-b]pyridine-4-carbaldehyde Pricemore >>

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Additional information on 3-bromo-1h-pyrrolo[2,3-b]pyridine-4-carbaldehyde

Recent Advances in the Application of 3-Bromo-1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde (CAS: 1159982-08-7) in Chemical Biology and Pharmaceutical Research

The compound 3-bromo-1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde (CAS: 1159982-08-7) has recently emerged as a key intermediate in the synthesis of novel bioactive molecules, particularly in the fields of oncology and infectious diseases. This heterocyclic aldehyde, featuring a pyrrolopyridine core, has garnered significant attention due to its versatile reactivity and potential as a pharmacophore. Recent studies have demonstrated its utility in the development of kinase inhibitors, antiviral agents, and other targeted therapies.

A 2023 study published in the Journal of Medicinal Chemistry highlighted the role of 3-bromo-1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde in the synthesis of selective JAK2 inhibitors. The researchers utilized this compound as a crucial building block to create a series of derivatives with improved potency and selectivity profiles. The bromo substituent at the 3-position proved particularly valuable for subsequent palladium-catalyzed cross-coupling reactions, enabling rapid diversification of the molecular scaffold.

In parallel developments, several research groups have explored the antiviral potential of derivatives based on this chemical structure. A recent preprint on bioRxiv described the synthesis and evaluation of 3-bromo-1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde derivatives as potential inhibitors of SARS-CoV-2 main protease. The aldehyde functionality was strategically employed in reductive amination reactions to generate a library of compounds with varying pharmacological properties.

The synthetic accessibility of 3-bromo-1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde has also been improved through recent methodological advances. A 2024 publication in Organic Letters detailed a novel one-pot synthesis approach that significantly increases the yield while reducing purification steps. This development is particularly important for scaling up production for preclinical and clinical studies.

From a structural perspective, computational chemistry studies have provided insights into the molecular interactions of derivatives containing this scaffold. Molecular docking simulations have shown that the planar pyrrolopyridine system can effectively engage in π-π stacking interactions with aromatic residues in protein binding sites, while the aldehyde group serves as a versatile handle for further structural modifications.

Looking forward, the unique combination of reactivity and biological activity displayed by 3-bromo-1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde suggests it will continue to play an important role in medicinal chemistry campaigns. Several pharmaceutical companies have included derivatives of this compound in their pipelines, particularly for immune-oncology applications. The coming years are likely to see additional structure-activity relationship studies and optimization efforts focused on this promising scaffold.

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