212908-12-8

Upstream product

• 7290-99-5 N,N-dimethyl-m-methoxybenzamide 
• 22921-68-2 2-bromo-5-methoxy-benzoic acid 
• 56658-04-9 2-bromo-5-methoxybenzoyl chloride 
• 124-40-3 dimethyl amine 

Downstream Products

• 497179-52-9 6-methoxy-2-methylisoindolin-1-one 
• 77973-25-2 1-(2-dimethylaminomethyl-4-methoxyphenyl)ethanone 
• 10126-37-1 (2-bromo-5-methoxyphenyl)-N,N-dimethylmethanamine 

Relevant academic research and scientific papers

Investigation of the mechanism of C(sp3)-H bond cleavage in Pd(0)-catalyzed intramolecular alkane arylation adjacent to amides and sulfonamides

The reactivity of C(sp3)-H bonds adjacent to a nitrogen atom can be tuned to allow intramolecular alkane arylation under Pd(0) catalysis. Diminishing the Lewis basicity of the nitrogen lone pair is crucial for this catalytic activity. A range of N-methylamides and sulfonamides react exclusively at primary C(sp3)-H bonds to afford the products of alkane arylation in good yields. The isolation of a Pd(II) reaction intermediate has enabled an evaluation of the reaction mechanism with a focus on the role of the bases in the C(sp3)-H bond cleaving step. The results of these stoichiometric studies, together with kinetic isotope effect experiments, provide rare experimental support for a concerted metalation-deprotonation (CMD) transition state, which has previously been proposed in alkane C(sp3)-H arylation. Moreover, DFT calculations have uncovered the additional role of the pivalate additive as a promoter of phosphine dissociation from the Pd(II) intermediate, enabling the CMD transition state. Finally, kinetic studies were performed, revealing the reaction rate expression and its relationship with the concentration of pivalate.

Cationic chalcone antibiotics. Design, synthesis, and mechanism of action

This paper describes how the introduction of "cationic" aliphatic amino groups in the chalcone scaffold results in potent antibacterial compounds. It is shown that the most favorable position for the aliphatic amino group is the 2-position of the B-ring, in particular in combination with a lipophilic substituent in the 5-position of the B-ring. We demonstrate that the compounds act by unselective disruption of cell membranes. Introduction of an additional aliphatic amino group in the á-ring results in compounds that are selective for bacterial membranes combined with a high antibacterial activity against both Gram-positive and -negative pathogens. The most potent compound in this study (78) has an MIC value of 2 μM against methicillin resistant Staphylococus aureus.

Simple and practical halogenation of arenes, alkenes and alkynes with hydrohalic acid/H2O2 or TBHP)

A simple protocol for the halogenation of arenes utilizing a combination of aqueous hydrogen peroxide (34 %) or tert-butylhydroperoxide (70 %) and hydrohalic acid is presented. A similar procure of oxyhalogenation involving the in situ generation of positive halogen reagents is applied for the preparation of vicinal trans-dibromoalkanes and dichloroalkanes from alkenes. The reaction of alkenes with a combination of hydrochloric acid and hydrobromic acid with hydrogen peroxide gave a mixture of 1-bromo 2-chloro alkanes and 1,2-dibromoalkanes: Oxidative bromination of alkynes is also reported under similar conditions.

Simple and efficient chlorination and bromination of aromatic compounds with aqueous TBHP (or H2O2) and a hydrohalic acid

A combination of aqueous tert-butylhydroperoxide (70%) or hydrogen peroxide (34%) and a hydrohalic acid was found effective in chlorination and bromination of aromatic compounds.