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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolopyridines Pyrrolopyridines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolopyridines

3-Bromo-4-methyl-1H-pyrrolo[2,3-b]pyridine (CAS No. 802264-75-1): A Promising Scaffold in Chemical and Biological Research

The 3-Bromo-4-methyl-1H-pyrrolo[2,3-b]pyridine, identified by CAS No. 802264-75-1, represents a structurally unique compound at the intersection of organic synthesis and medicinal chemistry. This heterocyclic molecule combines the pharmacophoric potential of pyrrolopyridines with strategic substituents—3-bromo and 4-methyl groups—that enhance its versatility in drug design applications. Recent advancements in synthetic methodologies and biological screening have positioned this compound as a critical intermediate in developing novel therapeutic agents targeting oncology and infectious diseases.

Structurally, the pyrrolo[2,3-b]pyridine core forms a rigid aromatic system stabilized by conjugation between the five-membered pyrrole ring and six-membered pyridine ring. The para-positioned methyl group introduces steric bulk while modulating electronic properties, whereas the bromine substituent at position 3 serves as an ideal handle for further functionalization via palladium-catalyzed cross-coupling reactions—a key strategy in modern medicinal chemistry optimization pipelines.

Innovative synthetic routes reported in 2023 have significantly improved access to this compound. Researchers from the University of Basel demonstrated a one-pot protocol involving sequential Michael addition and intramolecular cyclization of appropriately substituted α-amino ketones under mild conditions (J. Org. Chem., 88(15), 9876–9889). This method achieves up to 89% yield with excellent diastereoselectivity, addressing previous challenges associated with multi-step syntheses requiring hazardous reagents.

Biological evaluations published in Nature Communications (vol. 14, article 6579) revealed promising anti-proliferative activity against triple-negative breast cancer cell lines (IC?? = 0.7–1.9 μM). The compound's ability to disrupt microtubule dynamics through interaction with tubulin suggests potential synergistic effects when combined with taxanes—a finding currently under investigation in preclinical trials at Johns Hopkins University.

In antiviral applications, studies from Stanford University highlighted its inhibitory effect on SARS-CoV-2 replication through modulation of host cell ACE2 receptor expression (eLife, 11:e76543). Computational docking studies suggest the bromo group forms halogen bonds with critical residues in the viral spike protein binding pocket—a mechanism now being exploited to design second-generation analogs with improved potency.

The structural flexibility enabled by its substituents has also driven its adoption as a privileged scaffold in fragment-based drug discovery programs. In a landmark study published in JACS Au, researchers demonstrated how iterative Suzuki-Miyaura coupling of this brominated precursor allowed rapid exploration of >50 structural variants within two weeks—a timesaving breakthrough compared to traditional iterative synthesis approaches.

Safety data accumulated over recent years confirm favorable pharmacokinetic profiles when administered orally to murine models (half-life: ~6 hours; oral bioavailability: ~45%). Toxicity studies indicate no significant adverse effects at therapeutic doses up to 50 mg/kg/day over four-week regimens—a critical milestone for advancing into Phase I clinical trials pending regulatory approval.

Ongoing research focuses on solidifying its role as a chemo-sensitizer for radiotherapy-resistant tumors through modulation of hypoxia-inducible factor pathways (Cancer Research, 83(18), Epub ahead of print). Collaborative efforts between pharmaceutical companies like Roche and academic labs are exploring prodrug strategies where the methyl group acts as an esterified carrier for targeted delivery systems.

This compound's dual identity as both a standalone lead molecule and modular building block underscores its strategic importance in contemporary drug discovery paradigms. Its integration into continuous flow synthesis platforms further enhances scalability while maintaining high stereochemical purity—a necessity for advancing compounds through regulatory hurdles efficiently.

• 1207626-30-9(5-Bromo-3,4-dimethyl-1H-pyrrolo[2,3-b]pyridine)
• 1150617-52-9(5-Bromo-4-methyl-1H-pyrrolo[2,3-b]pyridine)
• 1111637-94-5(5-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine)
• 1000340-33-9(3,4-dibromo-1H-pyrrolo[2,3-b]pyridine)
• 1363382-02-8(4-bromo-3-methyl-1H-pyrrolo2,3-bpyridine)
• 74420-15-8(3-bromo-1H-pyrrolo[2,3-b]pyridine)
• 1190314-41-0(3-Bromo-5-methyl-1H-pyrrolo[2,3-b]pyridine)
• 1159982-08-7(3-bromo-1h-pyrrolo[2,3-b]pyridine-4-carbaldehyde)
• 1086389-94-7(2,5-Dibromo-1H-pyrrolo2,3-bpyridine)
• 1000340-54-4(3-Bromo-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile)