193979-43-0

Upstream product

• 1072-98-6 5-chloro-2-pyridylamine 
• 39225-30-4 ethyl 3-benzoyl-3-bromopropionate 
• 71-36-3 butan-1-ol 
• 6270-17-3 ethyl 3-benzoylpropanoate 
• 98-86-2 acetophenone 
• 15121-89-8 ethyl 3-benzoyl acrylate 
• 196959-66-7 C₁₂H₉ClN₂ 
• 623-47-2 propynoic acid ethyl ester 
• 100-52-7 benzaldehyde 
• 3278-34-0 ethyl 2-(ethoxythiocarbonylthio)acetate 
• 168837-18-1 6-chloro-2-phenylimidazo[1,2-a]pyridine 

Downstream Products

• 365213-62-3 (6-Chloro-2-phenyl-imidazo[1,2-a]pyridin-3-yl)-acetic acid 

Relevant academic research and scientific papers

Visible light/Ir(III) photocatalytic initiation of xanthate-based radical-chain reactions: Xanthate group transfer and oxidative addition to aromatic systems

A photocatalyzed redox generation of radicals from O-ethyl xanthates to generate electrophilic radicals under photoredox catalysis, using Ir(ppy)3 and blue LEDs irradiation is described. The protocol can be used in classical xanthate-based inter- and intra-molecular group transfer reactions and oxidative radical addition to several heteroaromatic systems. The process does not require high temperature and reactions are cleaner compared with the traditional peroxide initiation. In the oxidative addition to aromatic systems, the oxidation process is part of the catalytic cycle and does not require a stoichiometric oxidant such as DLP which is particularly difficult to separate from the product.

Xanthate-based microwave-assisted C–H radical functionalization of caffeine, 1,3-dimethyluracil, and imidazo[1,2-a]pyridines

Xanthate-based radical chemistry was used for the regioselective direct alkylation of caffeine, uracil, and imidazo[1,2-a]pyridine systems, using dilauroyl peroxide as initiator and oxidant, under microwave irradiation. Under these conditions, several electrophilic radicals (located alpha to a carbonyl function such as esters, amides, ketones, malonates and cyano groups) were added to the title heterocyclic systems. The methodology allows the intermolecular regioselective construction of a sp2-sp3C–C bond via a C–H functionalization in an aromatic substitution, from readily available starting materials.

Metal-free C-3 alkylation of imidazopyridines with xanthates and convenient access to alpidem and zolpidem

A metal-free process for the C-3 alkylation of imidazopyridines has been developed. Various alkylation products including alkyl ester-, cyano-, ketone- and amide-substituted imidazopyridines were prepared in good yields. With this method, a highly efficie

Copper(II)-Mediated Aerobic Synthesis of Imidazo[1,2-a]pyridines via Cascade Aminomethylation/Cycloisomerization of Alkynes

A single copper(II)-catalyzed three-component cascade aminomethylation/cycloisomerization of propiolates to form imidazo[1,2-a]pyridines was explored. A straightforward method was developed for the practical synthesis of functionalized imidazo[1,2-a]pyridines from benzaldehydes, 2-aminopyridines, and propiolate derivatives catalyzed by Cu(OAc)2 hydrate in the presence of air. The protocol is marked by excellent yields, functional group tolerance, and, above all, adaptability to synthesize imidazo[1,2-a]pyridine-based drug molecules such as Alpidem.

Flow chemistry synthesis of zolpidem, alpidem and other GABAA agonists and their biological evaluation through the use of in-line frontal affinity chromatography

The flow of information between chemical and biological research can present a bottleneck in pharmaceutical research. Tools that bridge these disciplines and aid information exchange have therefore clear value. Over the last few years, both synthetic chemistry and biological screening have benefited from automation, and a seamless chemistry-biology interface is now possible. We report here on the use of flow processes to perform synthesis and biological evaluation in an integrated manner. As proof of concept, a flow synthesis of a series of imidazo[1,2-a]pyridines, including zolpidem and alpidem, was developed and connected to a Frontal Affinity Chromatography screening assay to investigate their interaction with Human Serum Albumin (HSA). The Royal Society of Chemistry 2013.

Synthesis and binding affinity of 2-phenylimidazo[1,2-α]pyridine derivatives for both central and peripheral benzodiazepine receptors. A new series of high-affinity and selective ligands for the peripheral type

A number of 6-substituted or 6,8-disubstituted alkyl 2- phenylimidazo[1,2-a]pyridine-3-carboxylates 5a-h,-acetates 5i-s, 6a-g, and - propionates 5t, 6h and of N,N-dialkyl-2-phenylimidazo[1,2-α]pyridlne-3- carboxamides 7a-d, -aceramides 7e-t or -propionamide 7u were prepared following new synthetic methods, and their affinities for both the central (CBR) and the peripheral (PBR) benzodiazepine receptors evaluated. The compounds of the ester series displayed low affinity for both receptor types. Conversely, most of N,N-dialkyl(2-phenylimidazo[1,2-a]pyridin-3-yl)acetamides 7e-t proved to possess high affinity and selectivity for CBR or PBR depending on the nature of substituents at C(6)- and/or C(8) on the heterocyclic ring system. In particular, the 6-substituted compounds 7f-n displayed ratios of IC50 values (IC50(CBR)/IC50(PBR)) ranging from 0.32 (7m) to 232 (7k), while the 6,8-disubstituted compounds 7o-t were more than 1000-fold more selective for PBR versus CBR. Compounds 7f,m were examined in several different benzodiazepine receptor subtypes. Expression of specific GABA(A) receptor subunit assemblies in Xenopus oocytes was utilized to evaluate functionally both the efficacy and potency of the positive modulation of GABA-evoked C1+ currents by 7f and 7m in comparison with Zolpidem. The rank order of potencies of these drugs was 7f (EC50 = 3.2 x 10-8 M) > Zolpidem (EC50 = 3.6 x 10-8 M) > 7m (EC50 = 2.2 x 10-7 M). The actions of these compounds were also tested on α2β2γ2(s) receptors. However, the EC50 of these compounds was increased, compared to α1β2γ2(s) receptors, by 30-, 4-, and 5-fold for 7m, 7f, and Zolpidem, respectively. Finally, these compounds were almost completely devoid of activity at receptors containing the α5 subunit.