53484-16-5

Usage

Uses

Used in Organic Synthesis:
6-Bromo-1-methyl-1H-benzo[d]imidazole serves as a valuable building block in organic synthesis, particularly for the preparation of pharmaceuticals, agrochemicals, and materials. Its unique structure and reactivity make it a key component in the development of new chemical entities.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 6-Bromo-1-methyl-1H-benzo[d]imidazole is used as a precursor for the synthesis of biologically active compounds. It plays a crucial role in the creation of kinase inhibitors and antiviral agents, contributing to the advancement of treatments for various diseases.
Used in Agrochemical Industry:
6-Bromo-1-methyl-1H-benzo[d]imidazole also finds application in the agrochemical industry, where it is employed in the synthesis of compounds with pesticidal properties. Its use in this sector helps in the development of effective solutions for crop protection and management.
Used as a Reagent in Synthesis:
Furthermore, 6-Bromo-1-methyl-1H-benzo[d]imidazole functions as a reagent in the synthesis of a wide range of biologically active compounds. Its versatility in chemical reactions allows for the exploration of new synthetic pathways and the discovery of novel molecules with potential applications in various fields.

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

Upstream product

• 67-56-1 methanol 
• 337915-79-4 4-bromo-N²-methylbenzene-1,2-diamine 
• 122-51-0 orthoformic acid triethyl ester 
• 4887-88-1 5-bromo-1H-benzo[d]imidazole 
• 74-88-4 methyl iodide 
• 64-18-6 formic acid 
• 302800-13-1 5-bromo-N-methyl-2-nitroaniline 
• 321-23-3 4-bromo-2-fluoronitrobenzene 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 1616059-85-8 C₁₇H₁₆N₂O₂ 
• 1616059-76-7 3-(1-methyl-1H-benzo[d]imidazol-6-yl)phenol 
• 1616059-77-8 1-methyl-6-(3-(oxiran-2-ylmethoxy)phenyl)-1H-benzo[d]imidazole 
• 181867-19-6 1-methyl-1H-benzo[d]imidazole-6-carbaldehyde 
• 50591-23-6 1-methyl-1H-benzo[d]imidazol-6-ol 
• 26530-93-8 1-methyl-6-amino-1H-benzo[d]imidazole 
• 1616099-43-4 3-(1-methyl-1H-benzo[d]imidazol-6-yl)aniline 
• 10406-94-7 1-methyl-6-chloro-1H-benzo[d]imidazole 

Relevant academic research and scientific papers

Using Methanol as a Formaldehyde Surrogate for Sustainable Synthesis of N-Heterocycles via Manganese-Catalyzed Dehydrogenative Cyclization

The development of an efficient and sustainable synthetic route for formaldehyde production from renewable feedstock, especially in combination with a subsequent transformation to straightforwardly construct valuable chemicals, is highly desirable. Herein, we report a novel manganese-catalyzed dehydrogenative cyclization of methanol as a formaldehyde surrogate with a variety of dinucleophiles for facile synthesis of N-heterocycles. The in situ generated formaldehyde via catalytic methanol dehydrogenation can be selectively trapped by diverse dinucleophiles to avoid several possible side reactions. The utility of this transformation is further highlighted by its successful application to the synthesis of 13C-labeled N-heterocycles using 13CH3OH as a readily accessible 13C-isotope reagent.

Cu-Catalyzed C-H Allylation of Benzimidazoles with Allenes

CuH-catalyzed intramolecular cyclization and intermolecular allylation of benzimidazoles with allenes have been described. The reaction proceeded smoothly with the catalytic system of Cu(OAc)2/Xantphos and catalytic amount of (MeO)2MeSiH. This protocol features mild reaction conditions and a good tolerance of substrates bearing electron-withdrawing, electron-donating, or electron-neutral groups. A new catalytic mechanism was proposed for this copper hydride catalytic system.

Solvent-Controlled, Site-Selective N-Alkylation Reactions of Azolo-Fused Ring Heterocycles at N1-, N2-, and N3-Positions, Including Pyrazolo[3,4- d]pyrimidines, Purines, [1,2,3]Triazolo[4,5]pyridines, and Related Deaza-Compounds

Alkylation of 4-methoxy-1H-pyrazolo[3,4-d]pyrimidine (1b) with iodomethane in THF using NaHMDS as base selectively provided N2-methyl product 4-methoxy-2-methyl-2H-pyrazolo[3,4-d]pyrimidine (3b) in an 8/1 ratio over N1-methyl product (2b). Interestingly, conducting the reaction in DMSO reversed selectivity to provide a 4/1 ratio of N1/N2 methylated products. Crystal structures of product 3b with N1 and N7 coordinated to sodium indicated a potential role for the latter reinforcing the N2-selectivity. Limits of selectivity were tested with 26 heterocycles which revealed that N7 was a controlling element directing alkylations to favor N2 for pyrazolo- and N3 for imidazo- and triazolo-fused ring heterocycles when conducted in THF. Use of 1H-detected pulsed field gradient-stimulated echo (PFG-STE) NMR defined the molecular weights of ionic reactive complexes. This data and DFT charge distribution calculations suggest close ion pairs (CIPs) or tight ion pairs (TIPs) control alkylation selectivity in THF and solvent-separated ion pairs (SIPs) are the reactive species in DMSO.

BENZIMIDAZOLE DERIVATIVES AND USES THEREOF

Benzimidazole derivatives of Formula I, that modulate the activity of ACSS2 are disclosed for therapeutic use. The fused imidazole ring of the compounds disclosed has a diarylmethyl or diarylmethanol moiety attached at the 2-position and the compounds have at least one other substituent at the 5 or 6 position of the benzimidazole. Also disclosed are methods of using the benzimidazole compounds for the treatment of diseases or disorders, such as cancer.

PRMT5 INHIBITORS AND USES THEREOF

Described herein are compounds of Formula (A), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof:wherein Y1 is of formula (?) or formula (y):Ring Y is a 5- to 6-membered heteroaryl ring; and V4, V5, Rx, x, y, and n are as defined herein. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5-mediated disorders are also described.

PRMT5 INHIBITORS AND USES THEREOF

Described herein are compounds of formula (A), pharmaceutically acceptable salts thereof, and pharmaceutical com-positions thereof. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5-mediated disorders are also described.

BICYCLIC TRIAZOLES AS PROTEIN KINASE MODULATORS

The present disclosure provides bicyclic triazole protein kinase modulators and methods of using these compounds to treat diseases mediated by kinase activity.

4- (HETEROCYCLYL- FUSED PHENYL)- 3- (PHENYL OR PYRID -2- YL) PYRAZOLES AS INHIBITORS OF THE ALK-5- RECEPTOR

The invention relates to novel pyrazole derivatives which are inhibitors of the transforming growth factor, ("TGF")-β signalling pathway, in particular, the phosphorylation of smad2 or smad3 by the TGF-β type I or activin-like kinase ("ALK")-5 receptor, m