10406-94-7

Usage

Uses

Used in Pharmaceutical Industry:
1H-Benzimidazole,6-chloro-1-methyl-(9CI) is used as a pharmaceutical intermediate for the development of new drugs. Its unique structure and potential biological activity make it a promising candidate for the synthesis of compounds with therapeutic applications.
1H-Benzimidazole,6-chloro-1-methyl-(9CI) is also used as a research compound for studying its chemical and physical properties, as well as its potential interactions with biological systems. This can provide valuable insights into its possible uses and effects in medicine and pharmaceuticals.
Additionally, 1H-Benzimidazole,6-chloro-1-methyl-(9CI) may be utilized in the development of novel drug delivery systems, aiming to improve the efficacy and bioavailability of therapeutic agents.

InChI:InChI=1/C8H7ClN2/c1-11-5-10-7-3-2-6(9)4-8(7)11/h2-5H,1H3

Upstream product

• 64-18-6 formic acid 
• 84859-27-8 5-chloro-N¹-methylbenzene-1,2-diamine 
• 4887-82-5 6-chloro-benzoimidazole 
• 74-88-4 methyl iodide 
• 35966-84-8 4-chloro-2-methylaminonitrobenzene 
• 149-73-5 trimethyl orthoformate 
• 53484-16-5 6-bromo-1-methyl-1H-benzo[d]imidazole 
• 67-56-1 methanol 
• 89-63-4 4-Chloro-2-nitroaniline 
• 4887-82-5 5-chloro-1H-benzimidazole 
• 700-37-8 4-chloro-2-fluoro-nitrobenzene 

Relevant academic research and scientific papers

C2-Selective Branched Alkylation of Benzimidazoles by Rhodium(I)-Catalyzed C-H Activation

Herein, we report a Rh(I)/bisphosphine/K3PO4 catalytic system allowing for the first time the selective branched C-H alkylation of benzimidazoles with Michael acceptors. Branched alkylation with N,N-dimethyl acrylamide was successfully applied to the alkylation of a broad range of benzimidazoles incorporating a variety of N-substituents and with both electron-rich and -poor functionality displayed at different sites of the arene. Moreover, the introduction of a quaternary carbon was achieved by alkylation with ethyl methacrylate. The method was also shown to be applicable to the C2-selective branched alkylation of azabenzimidazoles.

Direct, Regioselective N-Alkylation of 1,3-Azoles

Regioselective N-alkylation of 1,3-azoles is a valuable transformation. Organomagnesium reagents were discovered to be competent bases to affect regioselective alkylation of various 1,3-azoles. Counterintuitively, substitution selectively occurred at the more sterically hindered nitrogen atom. Numerous examples are provided, on varying 1,3-azole scaffolds, with yields ranging from 25 to 95%.

Supercritical methanol as solvent and carbon source in the catalytic conversion of 1,2-diaminobenzenes and 2-nitroanilines to benzimidazoles

Benzimidazoles and N-methylbenzimidazoles were synthesized by simply heating 1,2-diaminobenzenes in supercritical methanol over copper-doped porous metal oxides. These catalysts were derived from synthetic hydrotalcites that only contain earth-abundant starting materials. The carbon equivalents needed for the construction of the benzimidazole core originated from the solvent itself, which is known to undergo reforming to hydrogen and carbon monoxide through the formation of a formaldehyde intermediate. A variety of 1,2-diaminobenzenes were converted to the corresponding mixtures of benzimidazoles and N-methylated analogues in good yields. Interestingly, the more challenging, but readily available 2-nitroanilines, which require an additional reduction step prior to cyclization, could also be successfully converted to benzimidazoles in high selectivity. Furthermore, various other alcohols were applied besides methanol, to obtain 2-alkyl- and 1,2-dialkylbenzimidazoles. Preliminary mechanistic insights into the origins of N-alkylation as well as the reactivity of the nitro derivatives are discussed.

ARYL PYRIDINE AS ALDOSTERONE SYNTHASE INHIBITORS

The present invention provides a compound of Formula (I); a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

A mild, one-pot synthesis of disubstituted benzimidazoles from 2-nitroanilines

A one-pot synthesis of disubstituted benzimidazoles from 2-nitroanilines is described. Hydrogenation of N-substituted 2-nitroanilines with palladium on carbon as catalyst in the presence of trimethyl orthoformate and catalytic pyridinium p-toluenesulfonate (PPTS) at room temperature provided good to excellent yields of the corresponding disubstituted benzimidazoles.

Hydroheteroarylation of alkynes under mild nickel catalysis

Nickel complexes having a bulky tri(sec-alkyl)phosphine ligand catalyze hydroheteroarylation of alkynes at 35 °C. Selective activation of an Ar-H bond over an Ar-CN bond of N-protected 3-cyanoindoles is achieved by a proper choice of ligand and/or an N-protecting group. The catalysis is applicable to a diverse range of heteroarenes to afford cis-hydroheteroarylation products in highly chemo- and stereoselective manners. Excellent regioselectivity is observed with unsymmetrical alkynes to give the corresponding heteroaryl-substituted ethenes having a larger substituent trans to an aryl group. Copyright