For chemists and procurement specialists in the pharmaceutical and fine chemical industries, understanding the synthetic pathways of key intermediates is fundamental. 3-Amino-4-iodopyridine (CAS 105752-11-2) is a crucial compound with documented applications, and knowledge of its synthesis aids in quality assessment and sourcing. This article outlines common methods to manufacture this important heterocyclic intermediate.

A prevalent route for synthesizing 3-Amino-4-iodopyridine involves the electrophilic iodination of a suitably protected 3-aminopyridine derivative. Often, the amino group is first protected, for instance, by acylation to form an amide. A common precursor is N-(pyridin-3-yl)pivalamide, derived from 3-aminopyridine. This protected intermediate can then undergo directed ortho-metalation. Treatment with a strong base, such as n-butyllithium, in the presence of a chelating agent like TMEDA at low temperatures, directs lithiation to the C-4 position adjacent to the protected amino group.

Following metalation, the resulting organolithium species is quenched with an iodine source, typically molecular iodine (I2), to introduce the iodine atom at the desired C-4 position. This yields the iodinated protected intermediate, N-(4-iodopyridin-3-yl)pivalamide. The final step involves the deprotection of the amino group, commonly achieved through acid hydrolysis, for example, using aqueous hydrochloric acid. This process regenerates the free amino group, yielding the target compound, 3-Amino-4-iodopyridine.

Alternatively, direct iodination of 4-aminopyridine has been explored, though it often requires careful optimization to achieve regioselectivity. Modern iodination reagents like N-Iodosuccinimide (NIS) can also be employed, sometimes in the presence of catalysts such as trifluoroacetic acid, to facilitate the electrophilic aromatic substitution more efficiently. These methods are crucial for industries looking to buy 3-Amino-4-iodopyridine with guaranteed purity.

The efficiency of these synthetic routes is critical for manufacturers aiming to provide a reliable supply of 3-Amino-4-iodopyridine. When you search for a “3-Amino-4-iodopyridine manufacturer” or inquire about “4-iodopyridin-3-ylamine price”, the underlying synthesis directly influences the quality and cost. Understanding these pathways allows researchers and procurement specialists to better assess the value proposition from different suppliers and make informed decisions for their organic synthesis projects.