22282-60-6

Usage

Uses

Used in Pharmaceutical Industry:
Pyridine, 2-iodo-4-methylis used as a critical intermediate for the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a key component in the development of new drugs and medications.
Used in Medicinal Chemistry:
Pyridine, 2-iodo-4-methylis used as a building block in the design and synthesis of new molecules with potential therapeutic applications. Its versatility in chemical reactions makes it a valuable tool for medicinal chemists in their quest to discover new drugs.
Used in Organometallic Chemistry:
Pyridine, 2-iodo-4-methylis used as a ligand in organometallic chemistry, where it can form stable complexes with metal ions. These complexes have potential applications in catalysis and materials science, contributing to the advancement of chemical processes and the development of new materials.

InChI:InChI=1/C6H6IN/c1-5-2-3-8-6(7)4-5/h2-4H,1H3

Upstream product

• 4926-28-7 2-Bromo-4-picoline 

Downstream Products

• 1243715-28-7 1-ethoxycarbonyl-7-methyl-3-phenethyindolizine 
• 30413-54-8 2-ethynyl-4-methylpyridine 

Relevant academic research and scientific papers

Cheap and easy synthesis of highly functionalized (het)aryl iodides via the aromatic finkelstein reaction

Aryl iodides are superior coupling partners in cross-couplingA- reactions compared to the corresponding chlorides or bromides. Unfortunately, the iodides are much more expensive, if commercially available at all, than the other halides. Thus, it is often mandatory to transform the available bromides into the corresponding iodides. The copper-catalyzed aromatic Finkelstein reaction turned out to be the method of choice to prepare a number of highly functionalized iodo(het)aryls, including pyridines, 2,2′-bipyridines, and chiral compounds. Georg Thieme Verlag Stuttgart? New York.

Homoleptic zincate-promoted room-temperature halogen-metal exchange of bromopyridines

Homoleptic lithium tri- and tetraalkyl zincates were reacted with a set of bromopyridines. Efficient and chemoselective bromine-metal exchanges were realized at room temperature with a substoichiometric amount of nBu 4ZnLi2·TMEDA reagent (1/3 equiv; TMEDA=N,N,N′,N′-tetramethylethylenediamine). This reactivity contrasted with that of tBu4ZnLi2·TMEDA, which was inefficient below one equivalent. DFT calculations allowed us to rationalize the formation of N...Li stabilized polypyridyl zincates in the reaction. The one-pot difunctionalization of dibromopyridines was also realized using the reagent stoichiometrically. The direct creation of C-Zn bonds in bromopyridines enabled us to perform efficient Negishi-type cross-couplings. Mild zincation! nBu4ZnLi2·TMEDA (in substoichiometric amounts) promoted efficient and chemoselective room-temperature bromine-metal exchange of a range of bromopyridines (see scheme). DFT calculations strongly supported the formation of a stabilized tripyridylzincate, which could be reacted with electrophiles or be directly involved in palladium-catalyzed cross-coupling reactions.