82626-72-0

Usage

Chemical Properties

Brown Solid

Uses

An intermediate for the synthesis of Alpidem.

Upstream product

• 59463-54-6 S-cyanomethyl O-ethyl carbonodithioate 
• 88964-99-2 6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine 
• 624-75-9 iodoacetonitrile 
• 1072-98-6 5-chloro-2-pyridylamine 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 590-17-0 cyanomethyl bromide 
• 99-91-2 para-chloroacetophenone 
• 75-05-8 acetonitrile 
• 151-50-8 potassium cyanide 
• 365213-33-8 [6-chloro-2-(4-chlorophenyl)-imidazo[1,2-a]pyridin-3-ylmethyl]-dimethylamine 

Relevant academic research and scientific papers

Synthesis of C3-Cyanomethylated Imidazo[1,2- a ]pyridines via Ultrasound-Promoted Three-Component Reaction under Catalyst- and Oxidant-Free Conditions

An efficient synthesis of C3-cyanomethylated imidazo[1,2-α]pyridines via ultrasound-promoted three-component reaction under catalyst-free, oxidant-free, and mild conditions has been developed. A series of C3-cyanomethylated imidazo[1,2-α]pyridines were rapidly prepared with satisfactory yields and good functional group compatibility. This strategy cloud also be applied to the synthesis of zolpidem and alpidem in short steps.

A cyanogen methylation imidazopyridine compound of preparation method (by machine translation)

The invention discloses a cyanogen methylation imidazopyridine compound of preparation method, in order to imidazo [1, 2 - a] pyridine compound as raw material, with the bromine second grade nitrile or [...] and under the action of the photocatalysis reaction, is obtained. Compared with the prior art, the method of the invention avoids the use of potassium cyanide or sodium cyanide and two connecting, iodomethane, and in the preparation of imidazo [1, 2 - a] pyridine compound of the cyanogen methylation product in the process, the chemical conversion from the original threestep shortened to step. The invention short preparation route, the preparation method is simple, the production cost is low, and the yield is high, have reduced the solvent to use and at the time of blowdown to the environment caused by pollution, easy to implement, easy to realize industrial. (by machine translation)

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.

Visible-Light-Induced Regioselective Cyanomethylation of Imidazopyridines and Its Application in Drug Synthesis

3-Cyanomethylated imidazopyridines were synthesized via a visible light-promoted reaction of imidazopyridines with bromoacetonitrile or iodoacetonitrile catalyzed by fac-Ir(ppy)3 under mild conditions. For the substrates with various substituents on benzene or pyridine ring, the reaction proceeded smoothly to give the corresponding products in moderate to good yields. The synthetic utility of this visible-light-induced reaction has been illustrated in the efficient synthesis of zolpidem and alpidem.

Iron-Catalyzed Dehydrogenative sp3-sp2 Coupling via Direct Oxidative C-H Activation of Acetonitrile

An iron-catalyzed dehydrogenative sp3-sp2 coupling of acetonitrile and 2-arylimidazo[1,2-a]pyridine has been realized, which can serve as a novel approach toward heteroarylacetonitriles. The merit of this strategy is illustrated by the breadth of functional groups tolerated in the transformation and the fast access to pharmaceuticals (such as zolpidem) directly from the heteroarylacetonitriles.

A structure-activity relationship study of the affinity of selected imidazo[1,2-a]pyridine derivatives, congeners of zolpidem, for the ω1-subtype of the benzodiazepine receptor

A series of 6-substituted 2-aryl-N,N-dimethylimidazol [1,2-a]pyridine-3-acetamides, congeners of zolpidem and alpidem, was synthesized and tested in vitro for binding with the benzodiazepine receptor in the competition with 3H-zolpidem as an ω1-selective radioligand. Molecular electrostatic potential (MEP) and the HOMO and LUMO energies were calculated for the compounds by semi-empirical quantum chemistry methods. The lipophilicity parameter of the compounds, expressed as the logarithm of the octanol-water partition coefficient (log P), was calculated; alternatively, standard values of the Hansch hydrophobic substituent constants π were used. In agreement with earlier investigations on the benzodiazepine receptor ligands with a high preference for the ω1-subtype, a quantitative correlation of the biological data with molecular parameters has revealed a significant dependence (r=0.954) of the binding affinity (IC50) on the deepest MEP minimum, in this case associated with the amide carbonyl oxygen atom. The lipophilicity parameters were found to be of lower significance.