5938-16-9

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
4-(4-Methoxyphenyl)pyridine is utilized as a building block for the synthesis of various pharmaceuticals and agrochemicals. Its molecular structure allows for the creation of new compounds with potential therapeutic or pesticidal properties, contributing to the development of innovative treatments and crop protection agents.
Used as a Ligand in Catalysis:
In the field of catalysis, 4-(4-Methoxyphenyl)pyridine serves as a ligand, enhancing the efficiency and selectivity of catalytic reactions. Its presence can modulate the activity of catalysts, facilitating specific transformations in organic synthesis and other chemical processes.
Used as a Precursor in Organic Synthesis:
4-(4-Methoxyphenyl)pyridine also functions as a precursor in organic synthesis, enabling the formation of a variety of complex organic molecules. Its reactivity and structural features make it a valuable intermediate in the preparation of specialized chemicals and materials.
Used in Medicinal Research:
4-(4-Methoxyphenyl)pyridine has demonstrated bioactive properties and is being explored for its potential medicinal applications. Researchers are investigating its interactions with biological targets, which may lead to the discovery of new drugs or therapeutic agents.
Overall, 4-(4-Methoxyphenyl)pyridine is a multifaceted chemical entity with a broad spectrum of applications in industrial and research settings, underscoring its importance in the advancement of science and technology.

InChI:InChI=1/C12H11NO/c1-14-12-4-2-10(3-5-12)11-6-8-13-9-7-11/h2-9H,1H3

Upstream product

• 110-86-1 pyridine 
• 849-83-2 bis(4-methoxybenzoyl) peroxide 
• 104-94-9 4-methoxy-aniline 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 93830-58-1 diethyl (pyridin-4-yl)borane 
• 15854-87-2 4-iodopyridine 
• 100-66-3 methoxybenzene 
• 35773-79-6 N-(methoxycarbonyl)pyridinium ion 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 5720-07-0 4-methoxyphenylboronic acid 
• 19524-06-2 4-bromopyridine hydrochloride 
• 259-79-0 bisbenzocyclobutene 
• 88345-97-5 3-bromo-4-(4'-methoxyphenyl)pyridine 
• 1692-15-5 4-pyridylboronic acid 

Downstream Products

• 1012886-81-5 4-(4'-methoxyphenyl)-1-(2-phenyl-allyl)pyridinium bromide 
• 39795-43-2 C₁₃H₁₄NO⁽¹⁺⁾*I^(1-) 
• 191602-60-5 4-(3-bromo-4-methoxyphenyl)pyridine 
• 196861-33-3 2-methoxy-5-(4-pyridinyl)phenylboronic acid 
• 80653-84-5 2-amino-4-(pyridin-4-yl)phenol 
• 1350737-69-7 4-(4-methoxyphenyl)-2-phenylpyridine 
• 144397-70-6 4-(pyridin-4-yl)benzonitrile 

Relevant academic research and scientific papers

Accessing Tricyclic Imines Comprising a 2-Azabicyclo[22.2]octane Scaffold by Intramolecular Hetero-Diels-Alder Reaction of 4-Alkenyl-Substituted N-Silyl-1,4-dihydropyridines

Tricyclic imines inheriting a 2-Azabicyclo[2.2.2]octane (isoquinuclidine) scaffold were provided with high regioselectivity in moderate to very good yields by a smooth, broadly applicable intramolecular hetero-Diels-Alder reaction of various 4-ω-Alkenyl-substituted 1,4-dihydropyridines (DHPs) under trifluoroacetic acid catalysis. The required? 4,4-disubstituted 1,4-DHPs were obtained by introduction of ω-Alkenyl moieties of varying chain length via diorganomagnesium reagents into the 4-position of diversely 4-substituted pyridines after prior N-Activation with triisopropylsilyltriflate.

Organocatalytic synthesis of (Het)biaryl scaffoldsviaphotoinduced intra/intermolecular C(sp2)-H arylation by 2-pyridone derivatives

A uniqueN,O-bidentate ligand 6-oxo-1,6-dihydro-pyridone-2-carboxylic acid dimethylamide (L1) catalyzed direct C(sp2)-H (intra/intermolecular) arylation of unactivated arenes has been developed to expedite access to (Het)biaryl scaffolds under UV-irradiation at room temperature. The protocol tolerated diverse functional groups and substitution patterns, affording the target products in moderate to excellent yields. Mechanistic investigations were also carried out to better understand the reaction pathway. Furthermore, the synthetic applicability of this unified approach has been showcasedviathe construction of biologically relevant 4-quinolone, tricyclic lactam and sultam derivatives.

Cobalt-catalyzed cross-coupling of nitrogen-containing heterocyclic phosphonium salts with arylmagnesium reagents

Cobalt-catalyzed cross-couplings of nitrogen-containing heterocyclic phosphonium salts with arylmagnesium halides proceeded efficiently with the aid of cobalt(II) catalyst and copper(I) salt in tetrahydrofuran at ambient temperature, producing the desired

Decarbonylative Pd-Catalyzed Suzuki Cross-Coupling for the Synthesis of Structurally Diverse Heterobiaryls

Heteroaromatic biaryls are core scaffolds found in a plethora of pharmaceuticals; however, their direct synthesis by the Suzuki cross-coupling is limited to heteroaromatic halide starting materials. Here, we report a direct synthesis of diverse nitrogen-containing heteroaromatic biaryls by Pd-catalyzed decarbonylative Suzuki cross-coupling of widely available heterocyclic carboxylic acids with arylboronic acids. The practical and modular nature of this cross-coupling enabled the straightforward preparation of >45 heterobiaryl products using pyridines, pyrimidines, pyrazines, and quinolines in excellent yields. We anticipate that the modular nature of this protocol will find broad application in medicinal chemistry and drug discovery research.

Magnetic chitosan-functionalized cobalt-NHC: Synthesis, characterization and catalytic activity toward Suzuki and Sonogashira cross-coupling reactions of aryl chlorides

Aryl chlorides are one of the most stable and available electrophiles, however, their coupling with nucleophiles remains a challenge in organic synthesis. Herein, we prepared a Cobalt-NHC (N-Heterocyclic carbene) complex anchored on magnetic chitosan nanoparticles and assayed its catalytic activity for the reactions of substituted phenylboronic acid and also phenlacetylene with derivatives of aryl chlorides. These reactions are of great importance since they are employed for the synthesis of unsymmetrical diarylethynes and biphenyls, which belong to a prime class of building blocks. The synthesized nanocatalyst was found to be highly efficient in Suzuki and Sonogashira coupling in terms of their activity and recyclability in polyethylene glycol (PEG) as a green reaction media under conditions of temperatures (70 and 100 °C) and Co loading (3 and 6 mol%). To the best of our knowledge, this is the first attempt of using cobalt-NHC complex for catalyzing the abovementioned reactions. Moreover, replacing the earth-abundant Cobalt-based catalyst as an alternative to high cost palladium make this approach promising from sustainable chemistry view.

Practical and Regioselective Synthesis of C-4-Alkylated Pyridines

The direct position-selective C-4 alkylation of pyridines has been a long-standing challenge in heterocyclic chemistry, particularly from pyridine itself. Historically this has been addressed using prefunctionalized materials to avoid overalkylation and mixtures of regioisomers. This study reports the invention of a simple maleate-derived blocking group for pyridines that enables exquisite control for Minisci-type decarboxylative alkylation at C-4 that allows for inexpensive access to these valuable building blocks. The method is employed on a variety of different pyridines and carboxylic acid alkyl donors, is operationally simple and scalable, and is applied to access known structures in a rapid and inexpensive fashion. Finally, this work points to an interesting strategic departure for the use of Minisci chemistry at the earliest possible stage (native pyridine) rather than current dogma that almost exclusively employs Minisci chemistry as a late-stage functionalization technique.

Base-Activated Latent Heteroaromatic Sulfinates as Nucleophilic Coupling Partners in Palladium-Catalyzed Cross-Coupling Reactions

Heteroaromatic sulfinates are effective nucleophilic reagents in Pd0-catalyzed cross-coupling reactions with aryl halides. However, metal sulfinate salts can be challenging to purify, solubilize in reaction media, and are not tolerant to multi-step transformations. Here we introduce base-activated, latent sulfinate reagents: β-nitrile and β-ester sulfones. We show that under the cross-coupling conditions, these species generate the sulfinate salt in situ, which then undergo efficient palladium-catalyzed desulfinative cross-coupling with (hetero)aryl bromides to deliver a broad range of biaryls. These latent sulfinate reagents have proven to be stable through multi-step substrate elaboration, and amenable to scale-up.

Sequential Ring-Opening and Ring-Closing Reactions for Converting para-Substituted Pyridines into meta-Substituted Anilines

Herein we report a method for converting para-substituted pyridine rings into meta-dialkylamino-substituted benzene rings through sequential ring-opening and ring-closing reactions. The nitrogen atom in the pyridine rings was replaced with a methine group, and a dialkylamino substituent was introduced onto the original unsubstituted carbon atom in the pyridine rings. This process can be formally regarded as a hybrid of the skeletal editing and C-H amination of pyridine rings.

Synthesis of Arylpalladium(II) Boronates: Confirming the Structure and Chemical Competence of Pre-transmetalation Intermediates in the Suzuki–Miyaura Reaction

Palladium(II) boronates are recognized as fundamental pre-transmetalation intermediates in Suzuki–Miyaura cross-couplings. While these typically transient species have been detected and studied spectroscopically, it is conspicuous that they have never been isolated since this important reaction was discovered over forty years ago. This study reports the synthesis of a family of unprecedented arylpalladium(II) boronates that are, by design, kinetically stable at ambient temperature, both in solution and in the solid state. These properties enabled unambiguous crystallographic confirmation of their structure for the first time and their chemical competence in a Suzuki–Miyaura reaction was demonstrated.

Quantifying Through-Space Substituent Effects

The description of substituents as electron donating or withdrawing leads to a perceived dominance of through-bond influences. The situation is compounded by the challenge of separating through-bond and through-space contributions. Here, we probe the experimental significance of through-space substituent effects in molecular interactions and reaction kinetics. Conformational equilibrium constants were transposed onto the Hammett substituent constant scale revealing dominant through-space substituent effects that cannot be described in classic terms. For example, NO2 groups positioned over a biaryl bond exhibited similar influences as resonant electron donors. Meanwhile, the electro-enhancing influence of OMe/OH groups could be switched off or inverted by conformational twisting. 267 conformational equilibrium constants measured across eleven solvents were found to be better predictors of reaction kinetics than calculated electrostatic potentials, suggesting utility in other contexts and for benchmarking theoretical solvation models.