3512-75-2

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-2,6-dimethylpyridine is used as a key building block for the synthesis of various pharmaceutical compounds. Its reactivity allows for the creation of a wide range of drug molecules, contributing to the development of new treatments and medications.
Used in Agrochemical Industry:
In the agrochemical sector, 4-Chloro-2,6-dimethylpyridine serves as a crucial component in the synthesis of pesticides. Its incorporation into these products enhances their effectiveness in controlling pests and diseases, thereby supporting agricultural productivity.
Used as an Intermediate in Chemical Production:
4-Chloro-2,6-dimethylpyridine is also utilized as an intermediate in the production of other chemicals. Its role in chemical synthesis processes is essential for obtaining specific end products, highlighting its importance in the broader chemical industry.

InChI:InChI=1/C7H8ClN/c1-5-3-7(8)4-6(2)9-5/h3-4H,1-2H3

Upstream product

• 3512-80-9 4-amino-2,6-lutidine 
• 7516-31-6 2,6-dimethyl-1H-pyridin-4-one 
• 6890-58-0 2,6-dimethylpyridine N-oxide hydrochloride 
• 121-44-8 triethylamine 
• 10025-87-3 trichlorophosphate 
• 42051-83-2 4-Hydroxy-2,6-dimethyl-pyridin-N-oxid 
• 108-48-5 2,6-dimethylpyridine 
• 1073-23-0 2,6-lutidine N-oxide 
• 81128-26-9 2,6-dimethyl-4-(trimethyl-stannyl)pyridine 
• 325142-95-8 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 
• 13603-44-6 2,6-dimethylpyridin-4-ol 
• 10026-13-8 phosphorus pentachloride 
• 7647-01-0 hydrogenchloride 
• 7782-77-6 cis-nitrous acid 

Downstream Products

• 28232-11-3 2,6-dimethyl-4-p-tolyloxy-pyridine 
• 20815-02-5 4-methoxy-2,6-dimethylpyridine 
• 857435-75-7 (2,6-dimethyl-[4]pyridyl)-phenyl-acetonitrile 
• 102077-21-4 4-benzyloxy-2,6-dimethyl-pyridine 
• 28232-10-2 2,6-dimethyl-4-m-tolyloxy-pyridine 
• 28232-09-9 2,6-dimethyl-4-o-tolyloxy-pyridine 
• 86776-04-7 (2,6-dimethyl-[4]pyridyl)-(2-nitro-phenyl)-amine 
• 86775-90-8 (2,6-dimethyl-pyridin-4-yl)-phenyl-amine 
• 855643-04-8 benzyl-(2,6-dimethyl-[4]pyridyl)-amine 
• 28223-15-6 2,6-dimethyl-4-phenoxy-pyridine 
• 101090-18-0 2-(2,6-dimethyl-[4]pyridyloxy)-benzoic acid methyl ester 
• 108-48-5 2,6-dimethylpyridine 
• 3512-80-9 4-amino-2,6-lutidine 

Relevant academic research and scientific papers

Electronic influence of substitution on the pyridine ring within NNN pincer-type molecules

Pincer molecules are of increasing interest due to the modular nature of modification and range of reactivity observed when coordinated to metal ions. A subset within the family of pincer molecules use a pyridine group to bridge the outer two arms as well as provide a N-donor atom for metal binding. While the arm appendages have been studied extensively, little research has been conducted on the electronic effects of the central, substituted pyridine systems. Therefore, a series of NNN pincer-type ligands with substitution on the 4-position of the pyridine ring with -OH, -OBn, -H, -Cl, and -NO2 functional groups were synthesized and characterized through NMR spectroscopy and ESI-HRMS. Each pincer was metalated with Cu(ii) salts and evaluated through X-ray diffraction analysis, cyclic voltammetry, and density functional theory analysis. The results indicate that the relatively unstudied -OBn group demonstrates both electron-withdrawing (XRD bond lengths) and electron-donating (NMR spectroscopy) properties. The -NO2 pincer ligand shows a redox event within experimental windows evaluated, in contrast to the other congeners studied. In addition, electron-donating groups increase the electron density around the Cu(ii) center based on DFT studies and cyclic voltammetry. These findings can be applied to other pyridine-based pincer systems when considering ligand design and warrants future characterization of 4-position substituted pyridines.

Synthesis of 12-Membered Tetra-aza Macrocyclic Pyridinophanes Bearing Electron-Withdrawing Groups

The number of substituted pyridine pyridinophanes found in the literature is limited due to challenges associated with 12-membered macrocycle and modified pyridine synthesis. Most notably, the electrophilic character at the 4-position of pyridine in pyridinophanes presents a unique challenge for introducing electrophilic chemical groups. Likewise, of the few reported, most substituted pyridine pyridinophanes in the literature are limited to electron-donating functionalities. Herein, new synthetic strategies for four new macrocycles bearing the electron-withdrawing groups CN, Cl, NO2, and CF3 are introduced. Potentiometric titrations were used to determine the protonation constants of the new pyridinophanes. Further, the influence of such modifications on the chemical behavior is predicted by comparing the potentiometric results to previously reported systems. X-ray diffraction analysis of the 4-Cl substituted species and its Cu(II) complex are also described to demonstrate the metal binding nature of these ligands. DFT analysis is used to support the experimental findings through energy calculations and ESP maps. These new molecules serve as a foundation to access a range of new pyridinophane small molecules and applications in future work.

Cobalt-Catalyzed C(sp2)-H Borylation: Mechanistic Insights Inspire Catalyst Design

A comprehensive study into the mechanism of bis(phosphino)pyridine (PNP) cobalt-catalyzed C-H borylation of 2,6-lutidine using B2Pin2 (Pin = pinacolate) has been conducted. The experimentally observed rate law, deuterium kinetic isotope effects, and identification of the catalyst resting state support turnover limiting C-H activation from a fully characterized cobalt(I) boryl intermediate. Monitoring the catalytic reaction as a function of time revealed that borylation of the 4-position of the pincer in the cobalt catalyst was faster than arene borylation. Cyclic voltammetry established the electron withdrawing influence of 4-BPin, which slows the rate of C-H oxidative addition and hence overall catalytic turnover. This mechanistic insight inspired the next generation of 4-substituted PNP cobalt catalysts with electron donating and sterically blocking methyl and pyrrolidinyl substituents that exhibited increased activity for the C-H borylation of unactivated arenes. The rationally designed catalysts promote effective turnover with stoichiometric quantities of arene substrate and B2Pin2. Kinetic studies on the improved catalyst, 4-(H)2BPin, established a change in turnover limiting step from C-H oxidative addition to C-B reductive elimination. The iridium congener of the optimized cobalt catalyst, 6-(H)2BPin, was prepared and crystallographically characterized and proved inactive for C-H borylation, a result of the high kinetic barrier for reductive elimination from octahedral Ir(III) complexes.

PYRAZOLOQUINOLINE DERIVATIVES

A compound and/or pharmacologically acceptable salt thereof represented by the formula (I) has PDE9 inhibitory action, so that the intracerebral cGMP concentration is anticipated to be elevated. The PDE9 inhibitory action and the increase in cGMP lead to the improvement of learning and memory behaviors, and the compound (I) has applicability as a therapeutic agent for cognitive dysfunctions in Alzheimer's disease. wherein R1 is a hydrogen atom; R2 is an aromatic ring group, etc.; R3 is a hydrogen atom, etc; R4 is a hydrogen atom; R5 is an oxepanyl group, etc.; R6 is a hydrogen atom.

Di-substituted pyridinyl aminohydantoins as potent and highly selective human β-secretase (BACE1) inhibitors

The identification of highly selective small molecule di-substituted pyridinyl aminohydantoins as β-secretase inhibitors is reported. The more potent and selective analogs demonstrate low nanomolar potency for the BACE1 enzyme as measured in a FRET assay, and exhibit comparable activity in a cell-based (ELISA) assay. In addition, these pyridine-aminohydantoins are highly selectivity (>500×) against the other structurally related aspartyl proteases BACE2, cathepsin D, pepsin and renin. Our design strategy followed a traditional SAR approach and was supported by molecular modeling studies based on the previously reported aminohydantoin 3a. We have taken advantage of the amino acid difference between the BACE1 and BACE2 at the S2′ pocket (BACE1 Pro70 changed to BACE2 Lys86) to build ligands with >500-fold selectivity against BACE2. The addition of large substituents on the targeted ligand at the vicinity of this aberration has generated a steric conflict between the ligand and these two proteins, thus impacting the ligand's affinity and selectivity. These ligands have also shown an exceptional selectivity against cathepsin D (>5000-fold) as well as the other aspartyl proteases mentioned. One of the more potent compounds (S)-39 displayed an IC50 value for BACE1 of 10 nM, and exhibited cellular activity with an EC50 value of 130 nM in the ELISA assay.

AZETIDINES AND CYCLOBUTANES AS HISTAMINE H3 RECEPTOR ANTAGONISTS

The invention relates to compounds of formula (I) wherein R, R0, R1, m, n and X1 to X4 have the meaning as cited in the description and the claims. Said compounds are useful as Histamine H3 receptor antagonists. The invention also relates to pharmaceutical compositions, the preparation of such compounds as well as the production and use as medicament.

Meta halogenation of 1,3-disubstituted arenes via iridium-catalyzed arene borylation

We report the meta halogenation of 1,3-disubstituted arenes to form 3,5-disubstituted aryl bromides and chlorides by using iridium-catalyzed arene borylation chemistry. Iridium-catalyzed borylation of arenes with B2pin2, followed by reaction of the boronic ester with copper(II) bromide or chloride converts arylboronic esters to the corresponding aryl halides. A variety of arenes containing alkoxy, alkyl, halogen, nitrile, ester, amide, and pivaloyl and TIPS-protected alcohols were converted to the corresponding 3,5-disubstituted aryl bromides and chlorides in yields ranging from 46% to 85%. In addition, 2,6-disubstituted and 3-substituted pyridines were converted to the 4-halo and 5-halopyridines, respectively. The utility of this methodology was demonstrated by the formal conversion of nicotine to Altinicline in three steps with an overall yield of 61% using meta bromination of nicotine as the first step. Copyright

Novel nevirapine-like inhibitors with improved activity against NNRTI-resistant HIV: 8-Heteroarylthiomethyldipyridodiazepinone derivatives

A series of 8-heteroarylthiomethyldipyridodiazepinone derivatives were prepared and evaluated for their antiviral profile against wild type virus and the important K103N/Y181C mutant as an indicator for broad activity. 2,6-Dimethylpyridine derivative 16 was found to have a good pharmacokinetic profile in spite of poor metabolic stability in rat liver microsomes.

Pyridinyl-quinolone compounds, their preparation and use

Fluorinated 1-cyclopropyl-7-(substituted-pyridinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids of the formula STR1 wherein R is hydrogen, R' and R" are hydrogen or fluoro, or other groups and Z is 3- or 4-pyridinyl substituted by alkyl groups or substituted alkyl groups, are superior antibacterial agents. They are prepared via a coupling reaction between the corresponding esters (R=alkyl) having a halo group in the 7-position and a substituted (trialkylstannyl)pyridine.

A Convenient Large Scale Synthesis of 2,6-Dimethyl-4-(trimethylstannyl)pyridine

Reaction of phosphorus oxychloride with 2,6-dimethylpyridine N-oxide hydrochloride (1) gave a mixture of 2-(chloromethyl)-6-methylpyridine (2) and 4-chloro-2,6-dimethylpyridine (3).Treatment of this mixture with triethylamine converted 2 to the quaterny salt 4 which was separated by water extraction leaving 3 which was subsequently reacted with trimethylstannyl sodium to yield 2,6-dimethyl-4-(trimethylstannyl)pyridine (6).