73583-37-6

Usage

Chemical Properties

Off-white Cryst

Uses

It is used in the synthesis of quaterpyridine nemertelline.

InChI:InChI=1/C5H3BrClN/c6-4-1-2-8-5(7)3-4/h1-3H

Upstream product

• 14432-12-3 4-Amino-2-chloropyridine 
• 52200-48-3 3-bromo-2-chloropyridine 
• 30766-03-1 4-bromo-2-picolinic acid 
• 14432-16-7 2-chloro-4-nitropyridine-N-oxide 
• 2402-95-1 2-chloropyridine-N-oxide 

Downstream Products

• 36404-88-3 2-chloro-3-carbaldehydepyridine 
• 458532-84-8 2-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine 
• 458532-96-2 2-chloropyridine-4-boronic acid 
• 633283-63-3 1-N-(tert-butoxycarbonyl)-4-N-(2-chloropyridin-4-yl)piperazine 
• 643082-10-4 2,2'-dichloro-3,4'-bipyridine 
• 916203-52-6 4-bromo-2-chloro-3-iodo-pyridine 
• 872973-93-8 7-chloro-1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-1,6-naphthyridin-2-(1H)-one 
• 916203-59-3 5-chloro-1-(2,6-dichlorophenyl)-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

Efficient Phosphorus-Free Chlorination of Hydroxy Aza-Arenes and Their Application in One-Pot Pharmaceutical Synthesis

The chlorination of hydroxy aza-arenes with bis(trichloromethyl) carbonate (BTC) and SOCl2 has been effectively performed by refluxing with 5 wt % 4-dimethylaminopyridine (DMAP) as a catalyst. Various substrates are chlorinated with high yields. The obtained chlorinated aza-arenes can be used directly with simple workup for succedent one-pot synthesis on a large scale.

Transition-metal-free decarboxylative halogenation of 2-picolinic acids with dihalomethane under oxygen conditions

A convenient and efficient method for the synthesis of 2-halogen-substituted pyridines is described. The decarboxylative halogenation of 2-picolinic acids with dihalomethane proceeded smoothly via N-chlorocarbene intermediates to afford 2-halogen-substituted pyridines in satisfactory to excellent yields under transition-metal-free conditions. This new type of decarboxylative halogenation is operationally simple and exhibits high functional-group tolerance.

Concise Entries to 4-Halo-2-pyridones and 3-Bromo-4-halo-2-pyridones

Methods for the synthesis of both simple 4-halo-2-pyridones and more functionalized 3,4-di- and (3,4,5-tri)-halo-2-pyridones are described that are based on a combination of Sandmeyer and regioselective (copper-mediated) halogenation, with a 2-chloro or a 2-benzyloxy moiety serving as a masked 2-pyridone.

Large-scale solvent-free chlorination of hydroxy-pyrimidines,-pyridines,- pyrazines and-amides using equimolar POCl3

Chlorination with equimolar POCl3 can be efficiently achieved not only for hydroxypyrimidines, but also for many other substrates such as 2-hydroxy-pyridines,-quinoxalines, or even-amides. The procedure is solvent-free and involves heating in a sealed reactor at high temperatures using one equivalent of pyridine as base. It is suitable for large scale (multigram) batch preparations.

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.

Arylpiperaszine derivatives, to the process for the production thereof and to the use thereof as therapeutic agents

The invention relates to compounds of the general formula (I): to the process for preparing them, and to the use thereof as a therapeutic agent.

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.

Migration du lithium en serie pyridinique: double catalyse et reformage. Acces aux derives de la bromo-2 lithio-3 pyridine et des bromo-4 halogeno-2 lithio-3 pyridines

The lithium of an organolithium-pyridinic derivative can be moved from one position to an another by an intermolecular reaction.Two new reactions are possible for pyridinic organic synthesis: the isomerisation of any lithio derivative to a more stable one, and a reaction that transforms a mixture of various bromo-lithio derivatives into a single one.The processes involved and the experimental tools used are described in terms of the 2-bromo-3-lithio- and 4-bromo-2-halogeno-3-lithiopyridines derivatives synthesis.