4926-54-9

Usage

Uses

Due to the limited information available on 5-bromo-3-methylH-imidazo[1,2-a]pyridine, its specific applications are not well-defined. However, as a chemical compound with a unique molecular structure, it may have potential uses in various industries, such as:
Used in Organic Chemistry Research:
5-bromo-3-methylH-imidazo[1,2-a]pyridine is used as a research compound for studying its chemical properties, reactivity, and potential applications in organic chemistry.
Used in Pharmaceutical Industry:
Although not well-documented, 5-bromo-3-methylH-imidazo[1,2-a]pyridine may be used as a building block or intermediate in the synthesis of pharmaceutical compounds, given its unique molecular structure.
Used in Chemical Synthesis:
5-bromo-3-methylH-imidazo[1,2-a]pyridine could be used as a reactant or catalyst in various chemical synthesis processes, depending on its reactivity and properties.

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

Upstream product

• 19798-81-3 2-Amino-6-bromopyridine 
• 19967-57-8 bromo-2 propanal 
• 74420-50-1 3-Methyl-5-aminoimidazo<1,2-a>pyridine 
• 141-86-6 2.6-diaminopyridine 
• 3400-55-3 2-bromopropionaldehyde diethyl acetal 

Relevant academic research and scientific papers

Unique Sulfur-Aromatic Interactions Contribute to the Binding of Potent Imidazothiazole Indoleamine 2,3-Dioxygenase Inhibitors

Indoleamine 2,3-dioxygenase (IDO1) inhibitors are speculated to be useful in cancer immunotherapy, but a phase III clinical trial of the most advanced IDO1 inhibitor, epacadostat, did not meet its primary end point and was abandoned. In previous work, we identified the novel IDO1 inhibitor N-(4-chlorophenyl)-2-((5-phenylthiazolo[2,3-c][1,2,4]triazol-3-yl)thio)acetamide 1 through high-throughput screening (HTS). Herein, we report a structure-activity relationship (SAR) study of this compound, which resulted in the potent IDO1 inhibitor 1-(4-cyanophenyl)-3-(3-(cyclopropylethynyl)imidazo[2,1-b]thiazol-5-yl)thiourea 47 (hIDO IC50 = 16.4 nM). X-ray cocrystal structural analysis revealed that the basis for this high potency is a unique sulfur-aromatic interaction network formed by the thiourea moiety of 47 with F163 and F226. This finding is expected to inspire new approaches toward the discovery of potent IDO1 inhibitors in the future.

HETEROCYCLIC COMPOUND

Provided is a compound having an antagonistic action on an NMDA receptor containing the NR2B subunit, and is useful as a prophylactic or therapeutic agent for major depression, bipolar disorder, migraine, pain, peripheral symptoms of dementia 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.