23742-35-0

Upstream product

• 583-68-6 2-bromo-p-toluidine 
• 4023-34-1 cyclopropanecarboxylic acid chloride 

Downstream Products

• 959855-39-1 2-cyclopropyl-6-methyl-1-(2-methylphenyl)-1H-benzimidazole 
• 1426228-32-1 N-(2-bromo-4-methylphenyl)-N-methylcyclopropanecarboxamide 
• 1156170-78-3 C₁₁H₁₄BrN 
• 1426327-88-9 N-(2-bromo-4-methylphenyl)-N-(cyclopropylmethyl)-1,1,1-trifluoromethanesulfonamide 

Relevant academic research and scientific papers

Synthesis of functionalized spiroindolines via palladium-catalyzed methine C-H arylation

The synthesis of cyclopropyl spiroindolines is described using an intramolecular palladium(0)-catalyzed C-H functionalization of a methine C(sp3)-H bond. This transformation can be coupled with intermolecular Suzuki couplings or direct arylations of heteroaromatics to access functionalized indoline scaffolds in a single step.

Silver-promoted, palladium-catalyzed direct arylation of cyclopropanes: Facile access to spiro 3,3′-cyclopropyl oxindoles

The Pd-catalyzed, Ag(I)-mediated intramolecular direct arylation of cyclopropane C-H bonds is described. Various spiro 3,3′-cyclopropyl oxindoles can be obtained in good to excellent yields from easily accessible 2-bromoanilides. The kinetic isotope effect was determined and epimerization studies were conducted, suggesting that the formation of a putative Pd-enolate is not operative and that the reaction proceeds via a C-H arylation pathway.

A palladium-catalyzed regiospecific synthesis of N-aryl benzimidazoles

(Chemical Equation Presented) Highly tolerated: A catalytic method employing [Pd2(dba)3] and XPhos or RuPhos permits the efficient synthesis of N-aryl benzimidazoles in regioisomerically pure form starting from ortho-halo-anilides (see scheme), and tolerates a wide range of functional groups, dba = trans,trans-dibenzylideneacetone.