53698-47-8

Usage

Uses

Used in Pharmaceutical Industry:
2-Methoxy-5-phenylpyridine serves as a crucial intermediate in the synthesis of various pharmaceuticals. Its unique structure and reactivity allow it to be incorporated into the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Production:
In the agrochemical sector, 2-Methoxy-5-phenylpyridine is utilized as a key component in the creation of pesticides and other agricultural chemicals. Its role in these applications is vital for enhancing crop protection and yield.
Used in the Production of Fine Chemicals:
2-Methoxy-5-phenylpyridine is also employed in the synthesis of fine chemicals, which are high-purity chemicals used in various industries, including fragrances, dyes, and other specialty applications. Its versatility and stability make it an essential component in these high-value chemical productions.

Upstream product

• 66600-05-3 2-chloro-5-phenylpyridine 
• 124-41-4 sodium methylate 
• 857436-23-8 N-(6-methoxy-[3]pyridyl)-N-nitroso-acetamide 
• 71-43-2 benzene 
• 624-28-2 2,5-dibromopyridine 
• 13472-85-0 2-methoxy-5-bromopyridine 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 
• 2996-92-1 phenyl trimethylsiloxane 
• 98-88-4 benzoyl chloride 
• 163105-89-3 2-methoxy-pyridine-5-boronic acid 
• 108-90-7 chlorobenzene 
• 108-86-1 bromobenzene 
• 445264-61-9 2-methoxy-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)pyridine 

Downstream Products

• 76053-45-7 2-hydroxy-5-phenylpyridine 

Relevant academic research and scientific papers

Monitoring chemical reactions by low-field benchtop NMR at 45 MHz: Pros and cons

Monitoring chemical reactions is the key to controlling chemical processes where NMR can provide support. High-field NMR gives detailed structural information on chemical compounds and reactions; however, it is expensive and complex to operate. Conversely, low-field NMR instruments are simple and relatively inexpensive alternatives. While low-field NMR does not provide the detailed information as the high-field instruments as a result of their smaller chemical shift dispersion and the complex secondary coupling, it remains of practical value as a process analytical technology (PAT) tool and is complimentary to other established methods, such as ReactIR and Raman spectroscopy. We have tested a picoSpin-45 (currently under ThermoFisher Scientific) benchtop NMR instrument to monitor three types of reactions by 1D 1H NMR: a Fischer esterification, a Suzuki cross-coupling, and the formation of an oxime. The Fischer esterification is a relatively simple reaction run at high concentration and served as proof of concept. The Suzuki coupling is an example of a more complex, commonly used reaction involving overlapping signals. Finally, the oxime formation involved a reaction in two phases that cannot be monitored by other PAT tools. Here, we discuss the pros and cons of monitoring these reactions at a low-field of 45 MHz by 1D 1H NMR.

Synthesis and anticancer activity of mitotic-specific 3,4-dihydropyridine-2(1h)-thiones

Most anticancer drugs target mitosis as the most crucial and fragile period of rapidly dividing cancer cells. However the limitations of classical chemotherapeutics drive the search for new more effective and selective compounds. For this purpose structur

Decarbonylative Suzuki-Miyaura Cross-Coupling of Aroyl Chlorides

Herein, we report a catalyst system for Pd-catalyzed decarbonylative Suzuki-Miyaura cross-coupling of aroyl chlorides with boronic acids to furnish biaryls. This strategy is suitable for a broad range of common aroyl chlorides and boronic acids. The synthetic utility is highlighted in the direct late-stage functionalization of pharmaceuticals and natural products capitalizing on the presence of carboxylic acid moiety. Extensive mechanistic and DFT studies provide key insight into the reaction mechanism and high decarbonylative cross-coupling selectivity.

The Hiyama Cross-Coupling Reaction at Parts Per Million Levels of Pd: In Situ Formation of Highly Active Spirosilicates in Glycol Solvents

A palladium NNC-pincer complex at a 5 mol ppm loading efficiently catalyzed the Hiyama coupling reaction of aryl bromides with aryl(trialkoxy)silanes in propylene glycol to give the corresponding biaryls in excellent yields. This method was applied to the syntheses of adapalene and a biaryl-type liquid-crystalline compound, as well as to the derivatization of dextromethorphan and norfloxacin. ESI-MS and NMR analyses of the reaction mixture suggested the formation of pentacoordinate spirosilicate intermediates in situ. Preliminary theoretical studies revealed that the glycol-derived silicate intermediates formed in situ are quite reactive silicon reagents in the transmetalation step.

Palladium-catalyzed decarbonylative Suzuki-Miyaura cross-coupling of amides by carbon-nitrogen bond activation

Palladium-catalyzed Suzuki-Miyaura cross-coupling or aryl halides is widely employed in the synthesis of many important molecules in synthetic chemistry, including pharmaceuticals, polymers and functional materials. Herein, we disclose the first palladium-catalyzed decarbonylative Suzuki-Miyaura cross-coupling of amides for the synthesis of biaryls through the selective activation of the N-C(O) bond of amides. This new method relies on the precise sequence engineering of the catalytic cycle, wherein decarbonylation occurs prior to the transmetallation step. The reaction is compatible with a wide range of boronic acids and amides, providing valuable biaryls in high yields (>60 examples). DFT studies support a mechanism involving oxidative addition, decarbonylation and transmetallation and provide insight into high N-C(O) bond activation selectivity. Most crucially, the reaction establishes the use of palladium catalysis in the biaryl Suzuki-Miyaura cross-coupling of the amide bond and should enable the design of a wide variety of cross-coupling methods in which palladium rivals the traditional biaryl synthesis from aryl halides and pseudohalides.

Cobalt-Catalyzed Cross-Coupling Reactions of Arylboronic Esters and Aryl Halides

An efficient cobalt catalyst system for the Suzuki-Miyaura cross-coupling reaction of arylboronic esters and aryl halides has been identified. In the presence of cobalt(II)/terpyridine catalyst and potassium methoxide, a diverse array of (hetero)biaryls have been prepared in moderate to excellent yields.

Pyridine sulfinates as general nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions with aryl halides

Pyridine rings are ubiquitous in drug molecules; however, the pre-eminent reaction used to form carbon-carbon bonds in the pharmaceutical industry, the Suzuki-Miyaura cross-coupling reaction, often fails when applied to these structures. This phenomenon is most pronounced in 2-substituted pyridines, and results from the difficulty in preparing, the poor stability of, and low efficiency in reactions of pyridine-2-boronates. We demonstrate that by replacing these boronates with pyridine-2-sulfinates, a cross-coupling process of unrivalled scope and utility is realized. The corresponding 3-And 4-substituted pyridine variants are also efficient coupling partners. In addition, we apply these sulfinates in a library format to the preparation of medicinally relevant derivatives of the drugs varenicline (Chantix) and mepyramine (Anthisan).

PYRIDINE DERIVATIVES AND APPLICATION OF ANTI-MACOBACTERIUM THEREOF

The present invention provides a series of pyridine derivatives and their preparation method and application thereof. The series of pyridine derivatives can be applied to treating mycobacterium-related diseases, especially to treatments of fatal mycobacterium-related diseases. The fatal diseases may be related to mycobacterium tuberculosis, mycobacterium bovis, mycobacterium avium, and mycobacterium marinum.

Pd-Catalyzed Ligand-Free Synthesis of Arylated Heteroaromatics by Coupling of N-Heteroaromatic Bromides with Iodobenzene Diacetate, Iodosobenzene, or Diphenyliodonium Salts

An efficient method for synthesizing arylated heteroaromatics has been reported via Pd-catalyzed ligand-free cross-coupling of N-heteroaromatic bromides with iodine(III) reagents under mild conditions. Iodobenzene diacetate, iodosobenzene, and diphenyliod

Oxygen-promoted Pd/C-catalyzed Suzuki-Miyaura reaction of potassium aryltrifluoroborates

A simple and highly efficient protocol has been developed for the Pd/C-catalyzed ligand-free Suzuki-Miyaura reaction of potassium aryltrifluoroborates. In this catalytic system, the results demonstrate that oxygen plays a positive role in the cross-coupling reaction. In addition, this catalytic system could be successfully applied to synthesize biaryl compounds containing a carbazole moiety and the catalyst was recycled seven times without significant loss of catalytic activity.