113577-68-7

Upstream product

• 18368-63-3 6-chloro-2-picoline 
• 5720-06-9 2-Methoxyphenylboronic acid 
• 67-56-1 methanol 
• 5315-25-3 2-bromo-6-methylpyridine 

Downstream Products

• 201607-63-8 2-(2-hydroxyphenyl)-6-methylpyridine 

Relevant academic research and scientific papers

NITROGENOUS HETEROCYCLIC AROMATIC COMPOUND, PREPARATION METHOD THEREFOR, PHARMACEUTICAL COMPOSITION THEREOF, AND APPLICATION THEREOF

Provided are a nitrogenous heterocyclic aromatic compound, a preparation method therefor, a pharmaceutical composition thereof, and an application thereof. The nitrogenous heterocyclic aromatic compound can be used for treating and/or preventing various diseases mediated by ALK5.

Synthesis of Chemically and Configurationally Stable Monofluoro Acylboronates: Effect of Ligand Structure on their Formation, Properties, and Reactivities

The recent disclosures of two classes of acylborons, potassium acyltrifluoroborates (KATs) and N-methyliminodiacetyl (MIDA) acylboronates, demonstrated that certain acylboron species can be both remarkably stable and uniquely reactive. Here we report new classes of ligands for acylboronates that have a significant influence on the formation, properties, and reactivities of acylboronates. Our systematic investigations identified a class of neutral, monofluoroboronates that can be prepared in a one step, gram-scale fashion from readily accessible KATs. These monofluoroboronates are stable to air, moisture, and silica gel chromatography and can be easily handled without any special precautions. X-ray crystallography, NMR spectroscopy, and HPLC studies showed that they are tetravalent, configurationally stable B-chiral acylboronates. Significantly, the ligands on the boronate allow for fine-tuning of the properties and reactivity of acylboronates. In amide-forming ligation with hydroxylamines under aqueous conditions, a considerable difference in reactivity was observed as a function of ligand structure. The solid-state structures suggested that subtle steric and conformational factors modulate the reactivities of the acylboronates.

Copper-catalyzed fluorination of 2-pyridyl aryl bromides

Copper(i)-catalyzed cross-coupling of aryl halides is the subject of extensive interest in synthetic chemistry, but the related catalytic fluorination is unsuccessful. Herein, we have developed a novel copper-catalyzed fluorination of aryl bromides using AgF as the fluorine source. In this transformation a pyridyl directing group is essential for successful catalytic fluorination. A XANES/EXAFS study indicated that the presence of the pyridyl group is essential to stabilize the Cu(i) species and accelerate oxidative addition of the aryl bromide. Further mechanistic studies implicated a Cu(i/iii) catalytic cycle in this Cu(i)-catalyzed fluorination, and final aryl C-F bond formation possibly proceeds through an irreversible reductive elimination of the ArCu(iii)-F species. This rare report of catalytic fluorination by a copper catalyst provides a valuable foundation for further development of Cu(i)-catalyzed fluorination of aryl halides.

α1-Adrenoceptor agonists: The identification of novel α1A subtype selective 2′-heteroaryl-2-(phenoxymethyl)imidazolines

Novel 2′-heteroaryl-2-(phenoxymethyl)imidazolines have been identified as potent agonists of the cloned human α1-adrenoceptors in vitro. The nature of the 2′-heteroaryl group can have significant effects on the potency, efficacy, and subtype selectivity in this series. α1A Subtype selective agonists have been identified.

The palladium catalysed Suzuki coupling of 2- and 4-chloropyridines

The Suzuki coupling of 2- and 4-chloropyridines with arylboronic acids is successfully performed under Pd(PPh3)4 catalysis. Moderate to good yields are obtained with 4-chloropyridines while 2-chloropyridines give excellent yields. The corresponding pyridine N-oxides react in the same manner. An easy and cheap access to arylpyridines, a class of compound with medicinal interest, is thus achieved.

Process for making 6-aryl-2-methylpyridines

This invention relates to a process for making 6-aryl-2-methylpyridines from substituted benzaldehydes by way of 1-aryl-1,5-diketones. The 6-aryl-2-methyl-pyridines made by this process can be used in preparing biologically active 6-aryl-pyridine thiosemicarbazones.