68223-13-2

Usage

InChI:InChI=1/C11H9NO/c13-11-5-3-9(4-6-11)10-2-1-7-12-8-10/h1-8,13H

Upstream product

• 82261-42-5 4-pyridin-3-ylaniline 
• 106-41-2 4-bromo-phenol 
• 1692-25-7 3-pyridylboronic acid 
• 2510-23-8 3-Ethynylpyridine 
• 54781-19-0 2-(trimethylsiloxy)cyclohexa-1,3-diene 
• 626-55-1 3-Bromopyridine 
• 71597-85-8 (p-hydroxyphenyl)boronic acid 
• 59020-10-9 3-(tributylstannyl)pyridine 
• 220565-63-9 pyridin-3-ylzinc(II) bromide 
• 540-38-5 p-Iodophenol 
• 929917-95-3 3-(4-Benzyloxy-phenyl)-pyridine 
• 626-60-8 3-Chloropyridine 
• 5720-07-0 4-methoxyphenylboronic acid 
• 5958-02-1 3-(4-methoxyphenyl)pyridine 

Downstream Products

• 85633-41-6 5-(3-pyridyl)salicylaldehyde 
• 925438-84-2 3-(4-{3-[4-(1-trityl-1H-imidazol-4-ylmethyl)-piperidin-1-yl]-propoxy}-phenyl)-pyridine 
• 319015-56-0 4-(pyridin-3-yl)phenyl sulfamate 
• 929917-96-4 (R)-2-[4-(4-pyridin-3-yl-phenoxy)-phenoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 1396803-60-3 1,2-bis[4-(pyridin-3-yl)phenoxy]ethane 
• 439608-06-7 2-amino-4-pyridin-3-yl-phenol 
• 1012886-71-3 C₁₂H₁₂NO⁽¹⁺⁾*I^(1-) 

Relevant academic research and scientific papers

Sequential Xanthalation and O-Trifluoromethylation of Phenols: A Procedure for the Synthesis of Aryl Trifluoromethyl Ethers

Molecules containing trifluoromethoxyaryl groups are of interest in pharmaceutical, agrochemical, and materials science research, due to their unique physical and electronic properties. Many of the known methods to synthesize aryl trifluoromethyl ethers require harsh reagents and highly controlled reaction conditions and rarely occur when heteroaromatic units are present. The two-step O-trifluoromethylation of phenols via aryl xanthates is one such method that suffers from these drawbacks. Herein, we report a method for the synthesis of aryl trifluoromethyl ethers from phenols by the facile conversion of the phenol to the corresponding aryl and heteroaryl xanthates with newly synthesized imidazolium methylthiocarbonothioyl salts and conversion of these xanthates to the trifluoromethyl ethers under mild reaction conditions.

High Throughput Experimentation and Continuous Flow Validation of Suzuki–Miyaura Cross-Coupling Reactions

Traditional methods to discover optimal reaction conditions for small molecule synthesis is a time-consuming effort that requires large quantities of material and a significant expenditure of labor. High-throughput techniques are a potentially transformative approach for reaction condition screening, however, rapid validation of the reaction hotspots under continuous flow conditions remains necessary to build confidence in high throughput screening hits. Continuous flow technology offers the opportunity to upscale the screening hotspots and optimize their output of the target compounds due to the exceptional heat and mass transfer ability of flow reactions that are conducted in a smaller and safer reaction volume. We report a robotic high throughput technique to execute reactions in multi-well plates that were coupled with fast mass spectrometric analysis using an autosampler to accelerate the reaction screening process. Palladium-catalyzed Suzuki–Miyaura cross-coupling reactions were screened in this system and a heat map was generated to identify the best reaction conditions for downstream scale-up under continuous flow. Here, high throughput experimentation reactions in 96-well plates were performed for 1 h at 50 °C, 100 °C, 150 °C, and 200 °C before diluting them into 384-well plates for mass analysis. With the aid of high throughput tools, 648 unique experiments were conducted in duplicate. The cross-coupling reactions were evaluated as a function of stoichiometry, temperature, concentration, order of addition, and substrate type. The hotspots from high throughput experimentation were examined using a microfluidic Chemtrix system that confirmed the positive reaction leads as true positives. Negative outcomes identified by these experiments were found to be true negatives by microfluidic reaction evaluation. Quantitation of product yields was performed using high-performance liquid chromatography-mass spectrometry (HPLC/MS-MS).

Facile synthesis of 3-arylpyridine derivatives by palladacycle-catalyzed Stille cross-coupling reaction

The Stille cross-coupling reaction of a variety of aryl halides (X=Cl, Br, I) with 3-alkylstannylpyridines highly catalyzed by cyclopalladated ferrocenylimine has been developed. This reaction allows formation of arylpyridine derivatives in moderate to excellent yields. Functional groups on aryl halides, such as amino, hydroxyl, keto, and aldehyde are tolerated and the reactions with arylbenzoxale substrates also proceed well.

Synthesis of functionalized arylpyridines and -pyrimidines by domino [4+2]/retro [4+2] cycloadditions of electron-rich dienes with alkynylpyridines and -pyrimidines

Aryl-substituted pyridines and pyrimidines were prepared by [4+2] cycloadditions of alkynyl-substituted pyridines and -pyrimidines with electron-rich dienes. The reactions proceed by formation of a bridged cycloadduct and subsequent thermal extrusion of ethylene. The pyridine moiety plays a crucial role for the success of the reaction.

2-Pyridyl and 3-pyridylzinc bromides: direct preparation and coupling reaction

A facile synthetic approach to the direct preparation of 2-pyridyl and 3-pyridylzinc bromides has been demonstrated using Rieke zinc with 2-bromopyridine and 3-bromopyridine, respectively. A variety of different electrophiles have been coupled with the resulting organozinc reagents to give the corresponding cross-coupling products in moderate to good yields.

Vesicular monoamine transporter substrate/inhibitor activity of MPTP/MPP+ derivatives: A structure-activity study

The active metabolite of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), N-methyl-4-phenylpyridinium (MPP+), selectively destroys the dopaminergic neurons and induces the symptoms of Parkinson's disease. Inhibition of mitochondrial complex

BIARYL SUBSTITUTED HETEROCYCLE INHIBITORS OF LTA4H FOR TREATING INFLAMMATION

The present invention relates to a chemical genus of biaryl substituted heterocycle inhibitors of LTA4H (leukotriene A4 hydrolase) useful for the treatment and prevention and prophylaxis of inflammatory diseases and disorders. The compounds have general formula Ψ: An example is

Reduction of CYP450 inhibition in the 4-[(1H-imidazol-4-yl)methyl] piperidine series of histamine H3 receptor antagonists

A novel series of histamine H3 receptor antagonists based on the 4-[(1H-imidazol-4-yl)methyl]piperidine template displaying low CYP2D6 and CYP3A4 inhibitory profiles has been identified. Structural features responsible for the reduction of P450 activity, a typical liability of 4-substituted imidazoles, have been established.

Pharmaceutical composition for the treatment of CNS and other disorders

The present invention relates to a method of treating disorders of the Central Nervous System (CNS) and other disorders in a mammal, including a human, by administering to the mammal a CNS-penetrant α7 nicotinic receptor agonist. It also relates to pharma

Pharmaceutical compositions for CNS and other disorders

The present invention relates to a method of treating disorders of the Central Nervous System (CNS) and other disorders in a mammal, including a human, by administering to the mammal a CNS-penetrant α7 nicotinic receptor agonist. It also relates to pharmaceutical compositions containing a pharmaceutically acceptable carrier and a CNS-penetrant α7 nicotinic receptor agonist.