74420-51-2

Usage

Uses

Used in Chemical Research and Drug Development:
5-Bromo-2-methylimidazo[1,2-a]pyridine is used as a chemical intermediate for the synthesis of various organic compounds and pharmaceuticals. Its unique structure allows it to be a valuable building block in the creation of new molecules with potential therapeutic applications.
Used in Toxicological Studies and Risk Assessments:
Due to its mutagenic and carcinogenic properties, 5-Bromo-2-methylimidazo[1,2-a]pyridine is used in toxicological studies to understand its effects on biological systems. This research is crucial for conducting risk assessments to determine safe exposure levels and to inform regulatory measures.
Used in Environmental Monitoring and Regulation:
As a potential environmental contaminant, 5-Bromo-2-methylimidazo[1,2-a]pyridine is utilized in environmental monitoring programs to detect its presence in various ecosystems. This helps in the development and enforcement of regulations aimed at controlling its release into the environment, thereby protecting both human health and ecological integrity.

InChI:InChI=1/C8H7BrN2/c1-6-5-11-7(9)3-2-4-8(11)10-6/h2-5H,1H3

Upstream product

• 19798-81-3 2-Amino-6-bromopyridine 
• 78-95-5 chloroacetone 

Relevant academic research and scientific papers

BICYCLIC COMPOUND AND PHARMACEUTICAL USE THEREOF

The present invention provides a compound represented by the formula wherein R1 is a hydrocarbon group optionally having substituent(s), amino optionally having substituent(s), hydroxy optionally having a substituent or a heterocyclic group optionally having substituent(s); R2 is a hydrogen atom or a hydrocarbon group optionally having substituent(s); Xa and Xb are each C, N, O or S; Xc and Xd are each C or N; m is 0-2; n is 1-3; ring A is a 5-membered ring optionally having substituent(s); ring B is a 6-membered ring optionally having substituent(s); and ring C is a 3- to 5-membered ring optionally having substituent(s), provided that when Xa, Xc and Xd are each C, then Xb is N or S, or a salt thereof, which is useful as an agent for the prophylaxis or treatment of a disease relating to an action of melatonin, and the like.

Reaction of 3-Substituted Imidazopyridines with Br+ and the Alleged 5-Bromo-Substituted Product

The reaction of 3-methylimidazopyridine with NBS was reinvestigated and is shown to give products formed by apparent nucleophilic substitution at the 2-position.NBS in CHCl3 gave compounds 4 and 6, while NBS in CCl4 or Br2 in CHCl3 gave exclusively 4.Mechanisms and differences in product formation are discussed; evidence that the previously reported NBS product was in fact 3-bromo-5-methylimidazopyridine, rather than the alleged 5-bromo-3-methyl derivative 3, is presented.Compound 3 was prepared by diazotization of 5-amino-3-methylimidazopyridine in the presence of HBr and by condensation of 2-bromopropanal (or its acetal) with 2-amino-6-bromopyridine (12).This latter reaction of the weakly basic aminopyridine 12 is shown to follow the normal pattern in which the amino nitrogen condenses with the carbonyl carbon.Structures are established by infrared, mass, and 1H-NMR spectral analyses, mechanistic considerations, and diagnostic reactions.Experimental and computer-generated 1H-NMR spectra of compounds 3 and 13 are reproduced.