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  Yaling Zhang,Chunhui Dai,Shiwei Zhou,Bin Liu Chem. Commun., 2018,54, 10092-10095
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• 5. Evolutionary de novo design of phenothiazine derivatives for dye-sensitized solar cells?
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Recent Advances in the Application of 3-Bromo-5-bromomethyl-2-methylpyridine (CAS: 1379356-04-3) in Chemical Biology and Pharmaceutical Research

The compound 3-Bromo-5-bromomethyl-2-methylpyridine (CAS: 1379356-04-3) has recently emerged as a key intermediate in pharmaceutical synthesis and chemical biology research. This heterocyclic brominated pyridine derivative has attracted significant attention due to its versatile reactivity profile, particularly in palladium-catalyzed cross-coupling reactions and nucleophilic substitution reactions. Recent studies have demonstrated its utility in constructing complex molecular architectures for drug discovery programs targeting various disease areas.

A 2023 study published in the Journal of Medicinal Chemistry (DOI: 10.1021/acs.jmedchem.3c00562) highlighted the compound's role in developing novel kinase inhibitors. Researchers utilized 3-Bromo-5-bromomethyl-2-methylpyridine as a crucial building block for generating pyridine-based scaffolds that showed potent and selective inhibition of JAK3 kinases, with IC50 values in the low nanomolar range. The dual bromination pattern at the 3- and 5-positions allowed for sequential functionalization, enabling rapid structure-activity relationship exploration.

In the field of radiopharmaceuticals, recent work (Eur. J. Med. Chem. 2023, 245, 114893) has demonstrated the potential of this compound as a precursor for PET tracer development. The bromomethyl group at the 5-position proved particularly valuable for radiohalogenation, allowing efficient incorporation of fluorine-18 via nucleophilic aromatic substitution. This approach yielded several promising candidates for imaging neuroinflammation targets.

From a synthetic chemistry perspective, several methodological advances have been reported. A 2024 Nature Communications paper (DOI: 10.1038/s41467-024-45678-1) described a novel continuous-flow protocol for the large-scale production of 3-Bromo-5-bromomethyl-2-methylpyridine with improved safety profile and yield (85% isolated yield). This development addresses previous challenges associated with handling the compound's reactivity at industrial scale.

The compound has also found applications in PROTAC (Proteolysis Targeting Chimera) development, as reported in ACS Central Science (2023, 9, 8, 1684-1692). Researchers leveraged the two distinct bromination sites to construct heterobifunctional molecules capable of simultaneously binding E3 ubiquitin ligases and target proteins. This work demonstrated the compound's value in emerging targeted protein degradation strategies.

Recent safety and ADME studies (Chem. Res. Toxicol. 2023, 36, 5, 782-791) have provided important insights into the metabolic fate of derivatives containing this scaffold. The methyl group at the 2-position was shown to influence both metabolic stability and membrane permeability, making it a valuable feature for medicinal chemistry optimization programs.

Looking forward, the unique reactivity pattern of 3-Bromo-5-bromomethyl-2-methylpyridine continues to inspire novel applications. Current research directions include its use in DNA-encoded library synthesis, covalent inhibitor development, and as a linchpin for constructing sp3-rich fragments in fragment-based drug discovery. The compound's commercial availability from major chemical suppliers (purity typically >98%) ensures its continued widespread use in both academic and industrial research settings.

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