4282-50-2

Usage

Uses

Used in Pharmaceutical Industry:
3-(3-nitrophenyl)pyridine is utilized as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs. Its structural properties allow it to be a component in the creation of molecules with specific therapeutic effects.
Used in Organic Chemistry:
In the field of organic chemistry, 3-(3-nitrophenyl)pyridine serves as a versatile intermediate for the synthesis of a range of organic compounds, leveraging its reactivity and functional groups to form diverse chemical entities.
Used in Medicinal Chemistry Research:
3-(3-nitrophenyl)pyridine is employed as a research tool in medicinal chemistry, where it aids in the exploration of new drug candidates and the understanding of molecular interactions relevant to therapeutic applications.
Safety Note:
It is important to acknowledge that 3-(3-nitrophenyl)pyridine is an irritant to the skin, eyes, and respiratory system. Therefore, it necessitates careful handling and adherence to safety protocols to minimize health risks during its use in laboratories and industrial settings.

InChI:InChI=1/C11H8N2O2/c14-13(15)11-5-1-3-9(7-11)10-4-2-6-12-8-10/h1-8H

Upstream product

• 110-86-1 pyridine 
• 2028-76-4 3-nitrophenyldiazonium chloride 
• 121-73-3 3-Nitrochlorobenzene 
• 1692-25-7 3-pyridylboronic acid 
• 13331-27-6 m-nitrobenzene boronic acid 
• 462-08-8 pyridin-3-ylamine 
• 4482-01-3 o-benzenedisulfonimide 
• 585-79-5 m-nitrobromobenzene 
• 645-00-1 m-iodonitrobenzene 
• 626-55-1 3-Bromopyridine 

Downstream Products

• 57976-57-5 3-(pyridin-3-yl)aniline 

Relevant academic research and scientific papers

Gold catalysed Suzuki-Miyaura coupling of arenediazonium o-benzenedisulfonimides

Arenediazonium o-benzenedisulfonimides have been used as efficient electrophilic partners in Au(I) catalysed Suzuki coupling reactions. The synthetic protocol is general, easy and produced either biaryls or heteroaryl arenes in good yields (51 positive examples, average yield 80%). o-Benzenedisulfonimide was recovered at the end of the reactions and was reused to prepare the starting salts for further reactions. Mechanistic insights suggest that the o-benzenedisulfonimide anion act as an electron transfer agent and promotes a catalytic cycle which does not require the presence of photocatalysts or external oxidants.

Carboxyamido/carbene ligated palladium (II) complex: A versatile catalyst for the synthesis of aryl-substituted heteroarenes

Carboxy amido/carbene ligated Pd-complex catalyzed Suzuki-Miyaura cross-coupling of aryl-boronic acids with heteroaryl bromides is described. The protocol has a broad substrate scope that includes electron-rich, electron-deficient and sterically hindered arylboronic acids and heteroaryl bromides. The catalytic activity of the catalyst has been further investigated in the coupling of 2,6-dibromopyridine with arylboronic acids.

METHOD OF SYNTHESIS MOLECULES USING CATALYST AND COMPOSITES THEREOF

A method to synthesis molecules is provided. The method employs a catalyst for a cross- coupling react ion to obtain the molecule. The method comprises coupling boronic acid and halide in presence of the catalyst having graphite oxide supported palladium nanoparticles, a solvent and a base by heating. The heating is performed at a temperature lower than the temperature at which the graphite oxide deforms. The molecule is a biaryl. The method further provides obtaining complexs such as boscalid, telmisartan, valsartan, and SPPARMγ.

Palladium nanoparticles on graphite oxide: A recyclable catalyst for the synthesis of biaryl cores

The synthesis of life saving drug molecules in a cost-effective and environmentally benign pathway is of paramount significance. We present an environment friendly protocol to prepare core moieties of top selling drug molecules such as boscalid and telmisartan using Suzuki-Miyaura coupling conditions. In contrast to the traditional synthesis of these pharmaceutically important molecules, we have accomplished a graphite oxide (GO) supported palladium nanoparticles (PdNPs) based catalyst which quantitatively produced these core biaryl moieties of top selling drug molecules in a recyclable way. The catalytic activity remained unchanged even after 16 successive catalytic cycles without incorporating any palladium metal impurity in the pharmaceutically significant organic products. A detailed study including IR spectroscopy, solid state NMR spectroscopy, X-ray photoelectron spectroscopy, and DFT calculation was employed to understand the role of solid support on the nondecaying recycling ability of the catalyst during the Suzuki-Miyaura coupling reaction. The study indicates a strong chemical interaction of the different functionalities present in the GO, with the palladium centers which is primarily responsible for such sustained catalytic activity during the consecutive Suzuki-Miyaura coupling cycles.

Arylation of pyridines via suzuki-miyaura cross-coupling and pyridine-directed C-H activation using a continuous-flow approach

Suzuki-Miyaura cross-coupling reactions between heteroaryl bromides and arylboronic acids were performed employing a continuous-flow approach using a simple flow reactor designed in-house. Pd(PPh3)4 was used as catalyst, and arylboronic acids containing both electron-withdrawing and electron-donating groups were applied. The coupling process required 23 minutes of residence time to be completed and generally good yields were obtained. Subsequent arylation of 2-phenyl pyridine was carried out via a C-H activation strategy using substituted bromobenzene compounds and a ruthenium(II) catalyst. To the best of our knowledge in this work we present for the first time the possibility of performing intermolecular C-H activation in a continuous-flow system. Georg Thieme Verlag Stuttgart, New York.

Iron-mediated direct suzuki-miyaura reaction: A new method for the ortho -arylation of pyrrole and pyridine

(Figure presented) The first example of an iron-mediated direct Suzuki-Miyaura reaction between N-heterocyclic compounds and arylboronic acids is described, and both electron-rich and electron-deficient heteroarenes can be successfully used for the coupling reaction.

Efficient diphosphane-based catalyst for the palladium-catalyzed suzuki cross-coupling reaction of 3-pyridylboronic acids

A highly active catalyst system derived from PdCl2 and 2,2',6,6'- tetramethoxy-4,4'-bis(diphenylphosphanyl)-3,3'-bi- pyridine (P-Phos) has been developed for the Suzuki cross- coupling reaction of pyridylboronic acid with a variety of aryl halides in good to excellent yields, even in the presence of hindered and functional groups. In addition, P-Phos also exhibited high activity in the palladium-catalyzed Suzuki reaction of 2,6-dimethoxypyridylboronic acid in excellent yields with a fast rate. The steric and electronic effects of the P- Phos-palladium complex to this cross-coupling reaction were also discussed.

Structurally simple inhibitors of lanosterol 14α-demethylase are efficacious in a rodent model of acute Chagas disease

We report structure-activity studies of a large number of dialkyl imidazoles as inhibitors of Trypanosoma cruzi lanosterol-14α-demethylase (L14DM). The compounds have a simple structure compared to posaconazole, another L14DM inhibitor that is an anti-Chagas drug candidate. Several compounds display potency for killing T. cruzi amastigotes in vitro with values of EC 50 in the 0.4-10 nM range. Two compounds were selected for efficacy studies in a mouse model of acute Chagas disease. At oral doses of 20-50 mg/kg given after establishment of parasite infection, the compounds reduced parasitemia in the blood to undetectable levels, and analysis of remaining parasites by PCR revealed a lack of parasites in the majority of animals. These dialkyl imidazoles are substantially less expensive to produce than posaconazole and are appropriate for further development toward an anti-Chagas disease clinical candidate.

NOVEL INDOL CARBOXYLIC ACID BISPYRIDYL CARBOXAMIDE DERIVATIVES, PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, PREPARATION METHOD AND COMPOSITION CONTAINING THE SAME AS AN ACTIVE INGREDIENT

Disclosed herein are a new indole carboxylic acid bispyridyl carboxamide derivative, a preparation method thereof, and a composition for prevention or treatment of obesity, urinary disorders, and CNS disorders, containing the same as an active ingredient. Because the indole carboxylic acid bispyridyl carboxamide derivatives according to the present invention have high affinity for 5-HT2c receptors, act selectively on the 5-HT2c receptors, the derivatives rarely have adverse effects caused by other receptors. Because the derivatives effectively inhibit serotonin activity, they may be useful for treatment or prevention of obesity; urinary disorders such as urinary incontinence, premature ejaculation, erectile dysfunction, and prostatic hyperplasia; CNS disorders such as depression, anxiety, concern, panic disorder, epilepsy, obsessive-compulsive disorder, migraine, sleep disorder, withdrawal from drug abuse, Alzheimer's disease, and schizophrenia, associated with 5-HT2c receptors.

Novel indol carboxylic acid bispyridyl carboxamide derivatives as 5-HT2c receptor antagonists

Disclosed herein are a new indole carboxylic acid bispyridyl carboxamide derivative, a preparation method thereof, and a composition for prevention or treatment of obesity, urinary disorders, and CNS disorders, containing the same as an active ingredient. Because the indole carboxylic acid bispyridyl carboxamide derivatives according to the present invention have high affinity for 5-HT2c receptors, act selectively on the 5-HT2c receptors, the derivatives rarely have adverse effects caused by other receptors. Because the derivatives effectively inhibit serotonin activity, they may be useful for treatment or prevention of obesity; urinary disorders such as urinary incontinence, premature ejaculation, erectile dysfunction, and prostatic hyperplasia; CNS disorders such as depression, anxiety, concern, panic disorder, epilepsy, obsessive-compulsive disorder, migraine, sleep disorder, withdrawal from drug abuse, Alzheimer's disease, and schizophrenia, associated with 5-HT2c receptors.