100727-17-1

Usage

Physical form

Yellow to white crystalline powder

Usage

Synthesis of pharmaceutical compounds and agrochemicals

Applications

Organic synthesis, development of drugs, pesticides, and specialty chemicals

Potential use

Treatment of various diseases, key intermediate in production of advanced materials

Properties

Useful in development of novel materials for industrial applications

Upstream product

• 142-08-5 2-hydroxypyridin 
• 70-11-1 α-bromoacetophenone 
• 109-00-2 3-HYDROXYPYRIDINE 
• 5633-34-1 (benzoylmethylene)dimethylsulfurane 
• 20912-84-9 Diphenylsulfonium phenacylid 
• 3282-32-4 2-diazo-acetophenone 
• 22918-00-9 2-hydroxypyridine silver salt 

Downstream Products

• 13472-81-6 3,5-dibromo-2-hydroxypyridine 

Relevant academic research and scientific papers

Human iPSC-derived cardiomyocytes and pyridyl-phenyl mexiletine analogs

In the United States, approximately one million individuals are hospitalized every year for arrhythmias, making arrhythmias one of the top causes of healthcare expenditures. Mexiletine is currently used as an antiarrhythmic drug but has limitations. The purpose of this work was to use normal and Long QT syndrome Type 3 (LQTS3) patient-derived human induced pluripotent stem cell (iPSC)-derived cardiomyocytes to identify an analog of mexiletine with superior drug-like properties. Compared to racemic mexiletine, medicinal chemistry optimization of substituted racemic pyridyl phenyl mexiletine analogs resulted in a more potent sodium channel inhibitor with greater selectivity for the sodium over the potassium channel and for late over peak sodium current.

Ruthenium-catalyzed chemoselective N?H bond insertion reactions of 2-pyridones/7-azaindoles with sulfoxonium ylides

A ruthenium-catalyzed highly chemoselective N-alkylation of 2-pyridones has been developed, affording N-alkylated 2-pyridone derivatives in good yields and excellent N-selectivity. The key to achieve this unprecedented N?H rather than O?H insertion reaction is the use of CpRu(PPh3)2Cl as the catalyst and sulfoxonium ylides as the alkylation reagents. Moreover, this protocol is also amenable to 7-azaindoles by slightly varying the reaction conditions. Furthermore, sulfonium ylides are also suitable alkylation reagents, providing the N-alkylated 2-pyridones in good selectivity.

HALOGENATION AND NITRATION OF 2-PYRIDONES

Halogenation of the 2-pyridones 2 afforded the corresponding mono-di- or tri-halo derivative depending on the conditions of the reaction.Nitration of 2a gave the dinitro-2-pyridone 4k, while nitration of 2c yielded the 3-nitro derivative 4p.Structures were confirmed by spectral data.