4,6-Dichloro-7-azaindole: Synthesis and Applications in Medicinal Chemistry
Medicinal chemistry constantly seeks novel molecular scaffolds that can serve as a basis for developing new therapeutic agents. Heterocyclic compounds, particularly those containing nitrogen, are of immense interest due to their prevalence in biologically active molecules. 4,6-Dichloro-7-azaindole, also known by its systematic name 4,6-Dichloro-1H-pyrrolo[2,3-b]pyridine (CAS 5912-18-5), is a prime example of such a valuable intermediate, offering a unique combination of structural features and reactivity for drug design.
The synthesis of 4,6-Dichloro-7-azaindole typically starts with the core 7-azaindole structure, which is then subjected to halogenation at the specific 4 and 6 positions. Modern synthetic strategies often involve sophisticated multi-step procedures designed for regioselectivity and high yield. For instance, N-oxidation followed by chlorination using reagents like phosphorus oxychloride (POCl3) is a commonly employed technique. The ability to reliably produce this compound with high purity (often exceeding 98%) is crucial for its utility in pharmaceutical synthesis, ensuring that downstream reactions proceed cleanly and the final API meets stringent quality standards. Manufacturers specializing in pharmaceutical intermediates, such as NINGBO INNO PHARMCHEM CO.,LTD., are adept at executing these complex syntheses at scale.
In medicinal chemistry, 4,6-Dichloro-7-azaindole is highly valued for its potential as a versatile building block. Its fused ring system mimics structural elements found in many bioactive natural products and synthetic drugs. The chlorine substituents at the 4 and 6 positions are particularly important; they can be readily displaced by various nucleophiles, allowing for the introduction of diverse pharmacophores. This facilitates the exploration of chemical space for drug candidates targeting a range of diseases, including but not limited to, infectious diseases (like tuberculosis, by synthesizing specific azaindole formamides) and oncology. Its structural relationship to purines and indoles also makes it a compelling scaffold for kinase inhibitors and other targeted therapies.
The utility of 4,6-Dichloro-7-azaindole is further enhanced by its potential for various coupling reactions, enabling the construction of more complex molecular architectures. For R&D scientists looking to purchase this intermediate, partnering with a dependable chemical supplier that prioritizes quality and offers technical support is essential. By providing this crucial building block, manufacturers empower medicinal chemists to accelerate their discovery pipelines and bring innovative treatments to market.
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Future Origin 2025
“For instance, N-oxidation followed by chlorination using reagents like phosphorus oxychloride (POCl3) is a commonly employed technique.”
Core Analyst 01
“The ability to reliably produce this compound with high purity (often exceeding 98%) is crucial for its utility in pharmaceutical synthesis, ensuring that downstream reactions proceed cleanly and the final API meets stringent quality standards.”
Silicon Seeker One
“Manufacturers specializing in pharmaceutical intermediates, such as NINGBO INNO PHARMCHEM CO.”