914253-86-4

Usage

Category

Pyridine family compound

Structure

Contains a pyridine ring with a 2,4-dimethylphenyl group attached

Usage

Mainly used as an intermediate in the pharmaceutical industry for drug synthesis and as a building block for other organic compounds

Physical Appearance

Yellow solid

Molecular Weight

187.25 g/mol

Melting Point

90-93°C

Significance

Valuable component in the development of new drugs and compounds with potential medicinal applications

Upstream product

• 4467-06-5 2-(4-methylphenyl)pyridine 
• 823-96-1 Trimethylboroxine 
• 109-04-6 2-bromo-pyridine 
• 1351117-44-6 C₁₂H₁₀FN 
• 544-97-8 dimethyl zinc(II) 
• 3385-78-2 trimethyl indium 
• 109-09-1 2-chloropyridine 
• 55499-44-0 2,4-dimethylbenzeneboronic acid 
• 80-43-3 bis(1-methyl-1-phenylethyl)peroxide 
• 5720-05-8 4-methylphenylboronic acid 
• 124-38-9 carbon dioxide 
• 6063-88-3 methoxydimethylaluminium 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 75722-64-4 2-(2,4,6-trimethylphenyl)pyridine 

Relevant academic research and scientific papers

Palladium-Catalyzed Electrochemical C-H Alkylation of Arenes

Palladium-catalyzed electrochemical C-H functionalization reactions have emerged as attractive tools for organic synthesis. This process offers an alternative to conventional methods that require harsh chemical oxidants. However, this electrolysis requires divided cells to avoid catalyst deactivation by cathodic reduction. Herein, we report the first example of palladium-catalyzed electrochemical C-H alkylation of arenes using undivided electrochemical cells in water, thereby providing a practical solution for the introduction of alkyl groups into arenes.

Triorganoindium reagents in Rh-catalyzed C–H activation/C–C cross-coupling reactions of 2-arylpyridines

The activation of C–H bonds through catalytic reactions using transition metals is an important challenge in organic chemistry in which the intermediates are related to those produced in the classical cross-coupling reactions. As part of our research program devoted to the development of metal-catalyzed reactions using indium organometallics, a protocol for the C–H activation and C–C coupling of 2-arylpyridines with triorganoindium reagents under Rh(I) catalysis is reported. Under the optimized conditions, we found that Me3In and Ar3In reagents reacted with 2-arylpyridines and related compounds in the presence of Rh(PPh3)3Cl, in PhCl/THF (9:1), at 120?C for 48 h, to afford the ortho-coupling products in moderate to good yields. The nitrogen atom in the pyridine ring acts as a directing group to assist the functionalization at the ortho position of the aryl group forming a new C–C bond at this position.

Enantioselective Synthesis of α-(Hetero)aryl Piperidines through Asymmetric Hydrogenation of Pyridinium Salts and Its Mechanistic Insights

Enantioselective synthesis of α-aryl and α-heteroaryl piperidines is reported. The key step is an iridium-catalyzed asymmetric hydrogenation of substituted N-benzylpyridinium salts. High levels of enantioselectivity up to 99.3:0.7 er were obtained for a range of α-heteroaryl piperidines. DFT calculations support an outersphere dissociative mechanism for the pyridinium reduction. Notably, initial protonation of the final enamine intermediate determines the stereochemical outcome of the transformation rather than hydride reduction of the resultant iminium intermediate.

Pd-PEPPSI Complexes bearing bulky [(1,2-Di-(tert-butyl)acenaphthyl] (DtBu-An) on N-heterocarbene backbones: Highly efficient for suzuki-miyaura cross-coupling under aerobic conditions

With the goal of achieving highly efficient palladium-catalyzed cross-coupling reactions under mild reaction conditions, the Pd-PEPPSI complexes C1 and C2 bearing 1,2-di(tert-butyl)acenaphthyl (DtBu-An) backbones were synthesized and characterized, and their use in Suzuki-Miyaura cross-coupling was investigated. The effects of catalyst structure and reaction conditions on the cross-coupling efficiency were evaluated in detail. The significant differences in catalytic activity compared with classical PEPPSI-IPr and PEPPSI-IPrAn precatalysts are discussed, where the axial sterics on the backbone play an important role. At low palladium loadings of 0.05-0.1 mol % and upon the addition of the relatively weak base K3PO4, the palladium complex C1 was found to be highly efficient for the coupling of (hetero)aryl chlorides with arylboronic acids under aerobic conditions, affording the corresponding biaryls in excellent yields.

Nickel-catalyzed N-heterocycle-directed cross-coupling of fluorinated arenes with organozinc reagents

Nickel-catalyzed N-heteroaromatics, such as pyridine, pyrazine or pyrimidine-directed cross-coupling of fluorinated arenes with organozinc reagents in the presence of sodium and PCy3 was reported.

Rhodium(I)-catalyzed direct carboxylation of arenes with CO2 via chelation-assisted C-H bond activation

Rh-catalyzed direct carboxylation of unactivated aryl C-H bond under atmospheric pressure of carbon dioxide was realized via chelation-assisted C-H activation for the first time. Variously substituted and functionalized 2-arylpyridines and 1-arylpyrazoles underwent the carboxylation in the presence of the rhodium catalyst and a stoichiometric methylating reagent, AlMe 2(OMe), to give carboxylated products in good yields. The catalysis is proposed to consist of methylrhodium(I) species as the key intermediate, which undergoes C-H activation to afford rhodium(III), followed by reductive elimination of methane to give nucleophilic arylrhodium(I). This approach demonstrates promising application of C-H bond activation strategy in the field of carbon dioxide fixation.

TRANSITION METAL-CATALYZED ALKYLATION OF C-H BONDS WITH ORGANOBORON REAGENTS

One aspect of the present invention relates to methods for functionalization of 2-arylpyridine and arylpyrazoles with organoboron reagents in the presence of a transition metal catalyst to furnish alkylated arylpyridines and arylpyrazoles via regioselective functionalization of sp2 -hybridized C-H bonds at a position ortho to the point of attachment of the pyridine or pyrazole ring to the aromatic nucleus, hi other embodiments, the present invention provides for alkylation of sp3-hybridized C-H bonds in alkylpyridines.

Palladium-catalyzed methylation of aryl C-H bond by using peroxides

A novel Pd(OAc)2-catalyzed methylation reaction by dicumyl peroxide via aryl C-H bond activation was discovered. Various 2-phenylpyridine and acetanilides can be used as reactants in these reactions. Peroxide was used as both the methylating reagent and the hydrogen acceptor. Copyright

Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids: Two distinct C-H activation pathways

Palladium-catalyzed alkylations of sp2 and sp3 C-H bonds with either methylboroxine or alkylboronic acids were developed. Ag2O or AgCO3 is used as a crucial oxidant and promoter for the transmetalation step. Ether, ester, alcohol, and alkene functional groups are tolerated. A new C-H activation pathway differing from the cyclometalation process is elucidated using methylboroxine as the coupling partner. Copyright

Solid phase synthesis of heterocycles

Methods for solid phase and combinatorial synthesis using a resin activation/capture approach are provided. In particular, methods for the production of dihydropyridones, N-acyidihydropyridones, tetrahydropyridones, pyridines, aminopyridines, N-acyltetrah