Production Method 1

7295-76-3

1331850-50-0

93560-55-5

Reaction Conditions

1.1 Reagents: Piperidine, 2,2,6,6-tetramethyl-, lithium salt (1:1) Solvents: Tetrahydrofuran ,  Hexane ;  5 min, 0 °C
1.2 Reagents: Dichloro(N,N,N′,N′-tetramethylethylenediamine)zinc ;  15 min, 0 °C
1.3 0 - 10 °C; 2 h, 20 °C
1.4 Reagents: Iodine Solvents: Tetrahydrofuran ;  overnight, 20 °C

Reference

Deprotometalation of substituted pyridines and regioselectivity-computed CH acidity relationships

Hedidi, Madani; Bentabed-Ababsa, Ghenia; Derdour, Aicha; Halauko, Yury S.; Ivashkevich, Oleg A.; et al, Tetrahedron, 2016, 72(17), 2196-2205

Production Method 2

7295-76-3

1331850-50-0

93560-55-5

142929-12-2

Reaction Conditions

1.1 Reagents: Butyllithium ,  2,2,6,6-Tetramethylpiperidine Solvents: Tetrahydrofuran ,  Hexane ;  15 min, 0 °C
1.2 0 - 10 °C; 2 h, rt
1.3 Reagents: Iodine Solvents: Tetrahydrofuran ;  overnight, rt

Reference

Deprotonative Metalation of Methoxy-Substituted Arenes Using Lithium 2,2,6,6-Tetramethylpiperidide: Experimental and Computational Study

Akimoto, Gaku; Otsuka, Mai; Takita, Ryo ; Uchiyama, Masanobu ; Hedidi, Madani; et al, Journal of Organic Chemistry, 2018, 83(21), 13498-13506

4-Iodo-3-methoxypyridine Raw materials

• 3-Methoxypyridine

4-Iodo-3-methoxypyridine Preparation Products

• 2-iodo-3-methoxy-pyridine (93560-55-5)
• 4-Iodo-3-methoxypyridine (1331850-50-0)
• 4,4'-Bipyridine, 3,3'-dimethoxy- (142929-12-2)

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Introduction to 4-Iodo-3-methoxypyridine (CAS No. 1331850-50-0)

4-Iodo-3-methoxypyridine, with the chemical formula C?H?INO?, is a versatile heterocyclic compound that has garnered significant attention in the field of pharmaceutical and chemical research. This compound, identified by its unique CAS No. 1331850-50-0, serves as a crucial intermediate in the synthesis of various biologically active molecules. Its molecular structure, featuring both an iodine substituent and a methoxy group on a pyridine ring, makes it particularly valuable for constructing complex pharmacophores.

The significance of 4-Iodo-3-methoxypyridine lies in its utility as a building block in medicinal chemistry. The presence of the iodine atom allows for further functionalization via cross-coupling reactions, such as Suzuki-Miyaura and Stille couplings, which are widely employed in the development of novel therapeutic agents. Additionally, the methoxy group enhances the compound's reactivity and stability, making it an ideal candidate for diverse synthetic applications.

In recent years, 4-Iodo-3-methoxypyridine has been extensively studied for its role in the development of small-molecule inhibitors targeting various disease pathways. For instance, researchers have leveraged this compound to design inhibitors of kinases and other enzymes involved in cancer metabolism. The pyridine core is particularly adept at mimicking natural substrates, allowing for high-affinity binding to biological targets. This has led to several promising candidates entering preclinical trials, showcasing the compound's potential in drug discovery.

One notable application of 4-Iodo-3-methoxypyridine is in the synthesis of antiviral agents. The structural motif of pyridine derivatives has been shown to interact effectively with viral proteases and polymerases, disrupting replication cycles. Recent studies have highlighted the use of this compound in generating inhibitors against RNA viruses, including those that cause severe respiratory infections. The ability to modify the pyridine ring further allows researchers to fine-tune properties such as solubility and metabolic stability, critical factors for therapeutic efficacy.

The industrial production of 4-Iodo-3-methoxypyridine (CAS No. 1331850-50-0) adheres to stringent quality control measures to ensure consistency and purity. Manufacturers employ advanced synthetic methodologies to optimize yield while minimizing byproducts. This is essential for downstream applications where impurities can significantly impact biological activity. Furthermore, green chemistry principles are increasingly being integrated into its synthesis, aiming to reduce environmental impact without compromising performance.

From a chemical biology perspective, 4-Iodo-3-methoxypyridine offers insights into enzyme-substrate interactions. Its scaffold can be used to develop probes that elucidate mechanistic details of enzymatic processes. Such probes are invaluable tools for understanding disease pathogenesis and identifying new therapeutic targets. The compound's reactivity also makes it suitable for generating libraries of derivatives through combinatorial chemistry approaches, enabling high-throughput screening for drug candidates.

The future prospects of 4-Iodo-3-methoxypyridine are vast, with ongoing research exploring its potential in areas beyond traditional pharmaceuticals. For example, its application in materials science is emerging as a promising field due to its ability to form coordination complexes with metal ions. These complexes exhibit unique optical and electronic properties that could be exploited in sensors or luminescent materials.

In conclusion,4-Iodo-3-methoxypyridine (CAS No. 1331850-50-0) stands as a cornerstone in modern synthetic chemistry and drug development. Its unique structural features enable diverse applications across multiple disciplines, from medicine to materials science. As research continues to uncover new functionalities and synthetic pathways, this compound will undoubtedly remain at the forefront of scientific innovation.

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