17744-99-9

Usage

InChI:InChI=1/C15H10ClN3/c16-12-6-4-11(5-7-12)15-13(8-9-17)19-10-2-1-3-14(19)18-15/h1-7,10H,8H2

Upstream product

• 151-50-8 potassium cyanide 
• 338415-39-7 1-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-N,N-dimethylmethanamine 
• 38922-74-6 2-(4-chlorophenyl)imidazolo[1,2-a]pyridine 
• 773837-37-9 sodium cyanide 
• 13138-21-1 diazoacetonitrile 
• 590-17-0 cyanomethyl bromide 
• 504-29-0 2-aminopyridine 
• 99-91-2 para-chloroacetophenone 
• 75-05-8 acetonitrile 

Downstream Products

• 1197849-65-2 C₁₉H₁₁Cl₂N₅ 
• 1197849-54-9 2-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-N'-hydroxyacetimidamide 
• 1197849-18-5 3-((2-(4-chlorophenyl)-6-fluoroimidazo[1,2-a]pyridin-3-yl)methyl)-N-hydroxy-1,2,4-oxadiazole-5-carboxamide 
• 1197849-43-6 N₁-(6-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)pyrimidin-4-yl)-N₂,N₂-dimethylethane-1,2-diamine 
• 1197849-10-7 3-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-1,2,4-oxadiazole-5-carbohydrazide 
• 1197849-04-9 ethyl 3-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-1,2,4-oxadiazole-5-carboxylate 
• 1197849-36-7 3-((6-fluoro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-1,2,4-oxadiazol-5(4H)-one 
• 1197849-66-3 6-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)pyrimidin-4-ol 
• 1197850-32-0 2-(4-chlorophenyl)-3-((6-chloropyrimidin-4-yl)methyl)imidazo[1,2-a]pyridine 

Relevant academic research and scientific papers

FeCl3-catalyzed C-3 functionalization of imidazo[1,2-a]pyridines with diazoacetonitrile under oxidant- and ligand-free conditions

A facile synthesis of 2-(imidazo[1,2-a]pyridin-3-yl)acetonitriles via FeCl3-catalyzed site-selective C(sp2)-H alkylation of imidazo[1,2-a]pyridines with diazoacetonitrile is presented. This new method features with an environmentally benign catalyst, easily obtainable substrates, and oxidant- and ligand-free reaction conditions. Moreover, the importance of the products thus obtained is showcased by their ready transformation into some synthetically and pharmaceutically interesting products with good efficiency.

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-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.

IMIDAZO[1,2-a]PYRIDINE COMPOUNDS

Imidazo[1,2-a]pyridines are disclosed. Compounds of the invention are useful therapeutic agents and their inclusion in pharmaceutical formulations and use in methods of treatment are disclosed.

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.