916203-52-6

Usage

Uses

Used in Pharmaceutical Research:
4-Bromo-2-chloro-3-iodopyridine is used as a building block for the synthesis of biologically active molecules in pharmaceutical research. Its unique structure and reactivity allow for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Research:
In agrochemical research, 4-Bromo-2-chloro-3-iodopyridine serves as a key intermediate in the synthesis of various pesticides and other chemical products. Its functional group compatibility enables the creation of novel agrochemicals with improved efficacy and selectivity.
Used in Materials Science:
4-Bromo-2-chloro-3-iodopyridine finds applications in the field of materials science, where it can be used to develop new materials with specific properties. Its versatile reactivity allows for the synthesis of materials with tailored characteristics for various applications.
Used in Organic Synthesis:
As a substituted pyridine derivative, 4-Bromo-2-chloro-3-iodopyridine is utilized in organic synthesis for the preparation of a wide range of organic compounds. Its unique structure and reactivity make it a valuable component in the synthesis of complex organic molecules for various industries.

InChI:InChI=1/C5H2BrClIN/c6-3-1-2-9-5(7)4(3)8/h1-2H

Upstream product

• 73583-37-6 2-chloro-4-bromopyridine 
• 14432-12-3 4-Amino-2-chloropyridine 

Downstream Products

• 916203-59-3 5-chloro-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one 
• 872973-93-8 7-chloro-1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-1,6-naphthyridin-2-(1H)-one 
• 444665-44-5 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-1,6-naphthyridin-2(1H)-one 
• 913556-82-8 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-1,6-naphthyridin-2(1H)-one 6-oxide 

Relevant academic research and scientific papers

Synthesis of a naphthyridone p38 MAP kinase inhibitor

Compound 1 is a p38 MAP kinase inhibitor potentially useful for the treatment of rheumatoid arthritis and psoriasis. A novel six-step synthesis suitable for large-scale preparation was developed in support of a drug development program at Merck Research Laboratories. The key steps include a tandem Heck-lactamization, N-oxidation, and a highly chemoselective Grignard addition of 4-(N-tert-butylpiperidinyl)-magnesium chloride to a naphthyridone N-oxide. The N-oxide exerted complete chemoselectivity via chelation in directing the Grignard addition to the α position as opposed to 1,4-addition on the enelactam. The dihydropyridyl adduct was in situ aromatized with isobutylchloroformate followed by heating in pyridine. Syntheses of Grignard precursor, N-tert-butyl-4-chloro-piperidine, were accomplished via transamination with a quaternary ammonium piperidone or via addition of methylmagnesium chloride to an iminium ion. Utilizing this chemistry, multi-kilogram preparation of compound 1 was successfully demonstrated. American Chemical Society.

Unique tandem heck-lactamization naphthyridinone ring formation between acrylanilides and halogenated pyridines

The Heck coupling of acrylanilides with 4-bromo-2-chloro-3-iodo-pyridine using palladium acetate can produce bis-Heck products or undergo an unusual tandem Heck-lactamization ring formation to generate 5-chloro-1-aryl-1,6- naphthyridin-2(1H)-ones.