Tag: 100-200

In 2022,Norman, Jacob P.; Larson, Nathaniel G.; Entz, Emily D.; Neufeldt, Sharon R. published an article in Journal of Organic Chemistry. The title of the article was 《Unconventional Site Selectivity in Palladium-Catalyzed Cross-Couplings of Dichloroheteroarenes under Ligand-Controlled and Ligand-Free Systems》.Safety of 2-Bromo-5-methylpyridine The author mentioned the following in the article:

This work represents the first highly selective method with a broad scope for C4-coupling of dihalogenated N-heteroarenes such as 2,4-dichloropyridine, 2,4-dichloroquinoline, 3,5-dichloro-4-phenylpyridazine, etc. where selectivity is clearly under ligand control. Under the optimized conditions, diverse substituted 2,4-dichloropyridines and related compounds undergo cross-coupling to form C4-C(sp2) and C4-C(sp3) bonds using organoboron, -zinc, and -magnesium reagents such as p-methoxyphenylboronic acid, cyclopentylmagnesium bromide, benzothiophenylzinc chloride, etc. The synthetic utility of this method is highlighted in multistep syntheses that combine C4-selective cross-coupling with subsequent nucleophilic aromatic substitution reactions. The majority of the products herein (71%) have not been previously reported, emphasizing the ability of this methodol. to open up underexplored chem. space. Remarkably, this work finds that ligand-free “”Jeffery”” conditions enhance the C4 selectivity of Suzuki coupling by an order of magnitude (>99:1). These ligand-free conditions enable the first C5-selective cross-couplings of 2,5-dichloropyridine and 2,5-dichloropyrimidine. In the experimental materials used by the author, we found 2-Bromo-5-methylpyridine(cas: 3510-66-5Safety of 2-Bromo-5-methylpyridine)

2-Bromo-5-methylpyridine(cas: 3510-66-5) belongs to pyridine. Pyridines form stable salts with strong acids. Pyridine itself is often used to neutralize acid formed in a reaction and as a basic solvent. Safety of 2-Bromo-5-methylpyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2022,Yang, Yu-Ting; Tu, Chang-Zheng; Shi, Jun-You; Yang, Xiao-Li; Liu, Jian-Jun; Cheng, Fei-Xiang published an article in Journal of Solid State Chemistry. The title of the article was 《Cu(I)-organic framework as a platform for high-efficiency selective adsorption of methylene blue and reversible iodine uptake》.Safety of 4-Cyanopyridine The author mentioned the following in the article:

A Cu(I)-MOF, {[Cu(4-PTZ)]·(H2O)0.5}n (1), that contains rhombic channels with the size of 10.174 Å x 16.965 Å was obtained based on in situ generated 5-(4-pyridyl)-1H-tetrazole ligand (4-HPTZ). Compound 1 not only displays remarkable capability for selective adsorption toward the organic dye Methylene Blue (149.5 mg g-1), but also shows reversible adsorption of I2 mols. in hexane medium (96.2%). Therefore, compound 1 should be a promising MOF-based bifunctional adsorbent in the field of pollutant removal. In the experiment, the researchers used many compounds, for example, 4-Cyanopyridine(cas: 100-48-1Safety of 4-Cyanopyridine)

4-Cyanopyridine(cas: 100-48-1) belongs to pyridine. Pyridines are often used as catalysts or reagents; particular notice has been paid recently to how pyridine coordinates to metal centers enabling a wide range of valuable reactions. Safety of 4-Cyanopyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Jang, Mingyeong; Lim, Taeho; Park, Byoung Yong; Han, Min Su published an article in 2022. The article was titled 《Metal-Free, Rapid, and Highly Chemoselective Reduction of Aromatic Nitro Compounds at Room Temperature》, and you may find the article in Journal of Organic Chemistry.Formula: C5H5BrN2 The information in the text is summarized as follows:

A metal-free and highly chemoselective method for the reduction of aromatic nitro compounds, RNO2 (R = 4-BrC6H4, quinolin-6-yl, 2-methyl-1,3-benzoxazol-6-yl, etc.) has been described. This reduction was performed using tetrahydroxydiboron [B2(OH)4] as the reductant and 4,4′-bipyridine as the organocatalyst and could be completed within 5 min at room temperature Under optimal conditions, nitro compounds RNO2 with sensitive functional groups, such as vinyl, ethynyl, carbonyl, and halogen, were converted into the corresponding amines, RNH2 with excellent selectivity while avoiding the undesirable reduction of the sensitive functional groups. In the part of experimental materials, we found many familiar compounds, such as 6-Bromopyridin-3-amine(cas: 13534-97-9Formula: C5H5BrN2)

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. Amines can be classified according to the nature and number of substituents on nitrogen. Aliphatic amines contain only H and alkyl substituents. Aromatic amines have the nitrogen atom connected to an aromatic ring.Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine (NClH2).Formula: C5H5BrN2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2019,Chemistry – A European Journal included an article by Nihei, Masayuki; Yanai, Yuta; Natke, Dominik; Takayama, Ryo; Kato, Marina; Sekine, Yoshihiro; Renz, Franz; Oshio, Hiroki. Synthetic Route of C12H12N2. The article was titled 《Solid-State Hydrogen-Bond Alterations in a [Co2Fe2] Complex with Bifunctional Hydrogen-Bonding Donors》. The information in the text is summarized as follows:

A hydrogen-bonding donor-acceptor system, [Co2Fe2(bpy*)4(CN)6(tp*)2](PF6)2·2ABA·4BN·2PE (1Solv), was prepared by co-crystallization of an external stimuli-responsive cyanide-bridged tetranuclear [Co2Fe2] complex and bifunctional hydrogen-bonding donors, p-aminobenzoic acid. Compound 1Solv exhibited a gradual electron-transfer-coupled spin transition (ETCST), and the removal of solvent mols. led to an abrupt thermal ETCST behavior with increased transition temperature X-ray structural anal. revealed that the modification of ETCST was caused by a significant alteration of a hydrogen-bonding mode between the tetranuclear [Co2Fe2]2+ cations and ABA mols. Variable temperature IR measurements indicated that the desolvated form, 1desolv, showed dynamic alteration of hydrogen-bonding interactions coupled with thermal ETCST behavior. These results suggested that the tetranuclear [Co2Fe2] complex shows solid-state modulations of hydrogen-bond strengths by external stimuli. In the part of experimental materials, we found many familiar compounds, such as 4,4′-Dimethyl-2,2′-bipyridine(cas: 1134-35-6Synthetic Route of C12H12N2)

4,4′-Dimethyl-2,2′-bipyridine(cas: 1134-35-6) is used as a chemical Intermediate. It can be used for the determination of ferrous and cyanide compounds.Synthetic Route of C12H12N2 Furthermore, 4,4′-Dimethyl-2,2′-bipyridine is used in the synthesis of a series of o-phenanthroline-substituted ruthenium(II) complexes.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2019,Journal of Organic Chemistry included an article by Yoritate, Makoto; Londregan, Allyn T.; Lian, Yajing; Hartwig, John F.. Product Details of 53939-30-3. The article was titled 《Sequential Xanthalation and O-Trifluoromethylation of Phenols: A Procedure for the Synthesis of Aryl Trifluoromethyl Ethers》. The information in the text is summarized as follows:

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, author 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. In the experimental materials used by the author, we found 5-Bromo-2-chloropyridine(cas: 53939-30-3Product Details of 53939-30-3)

5-Bromo-2-chloropyridine(cas: 53939-30-3) belongs to pyridine. In industry and in the lab, pyridine is used as a reaction solvent, particularly when its basicity is useful, and as a starting material for synthesizing some herbicides, fungicides, and antiseptics.Product Details of 53939-30-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2019,Chemistry – A European Journal included an article by Sinha, Narayan; Heijnen, Dorus; Feringa, Ben L.; Organ, Michael G.. SDS of cas: 53939-30-3. The article was titled 《Murahashi cross-coupling at -78 °C: a one-pot procedure for sequential C-C/C-C, C-C/C-N and C-C/C-S cross-coupling of bromo-chloro-arenes》. The information in the text is summarized as follows:

The coupling of organolithium reagents, including strongly hindered examples, with (hetero)aryl bromides at cryogenic temperatures (as low as -78 °C) was achieved with high-reactivity Pd-NHC catalysts to obtain arenes. A temperature-dependent chemoselectivity trigger was developed for synthesis of arenes by selective coupling of aryl bromides in the presence of chlorides. Building on this, a one-pot, sequential coupling strategy was presented for the rapid construction of arenes, amines and thioethers. Importantly, preparation of arenes by one-shot addition of alkyllithium compounds to Pd cross-coupling reactions was achieved, eliminating the need for slow addition by syringe pump. After reading the article, we found that the author used 5-Bromo-2-chloropyridine(cas: 53939-30-3SDS of cas: 53939-30-3)

5-Bromo-2-chloropyridine(cas: 53939-30-3) belongs to pyridine. In industry and in the lab, pyridine is used as a reaction solvent, particularly when its basicity is useful, and as a starting material for synthesizing some herbicides, fungicides, and antiseptics.SDS of cas: 53939-30-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2018,Wang, Dong; Shen, Meng; Wang, Yuxi; Hu, Jianyong; Zhao, Junjie; Yu, Peng published 《Access to Furo[2,3-b]pyridines by Transition-Metal-Free Intramolecular Cyclization of C3-substituted Pyridine N-oxides》.Asian Journal of Organic Chemistry published the findings.HPLC of Formula: 53939-30-3 The information in the text is summarized as follows:

Two transition-metal-free synthetic methods for the construction of furo[2,3-b]pyridines such as I [R = H, 5-F, 5-Me, etc.; R1 = Me, Et, Ph, etc.; R2 = Me, Et, Ph, etc.] from corresponding C3-substituted-pyridine-N-oxides were developed by regioselective intramol. nucleophilic addition/rearomatization strategy. Remarkable features of these methods include simple operation, wide substrate scope and easily accessible starting materials. After reading the article, we found that the author used 5-Bromo-2-chloropyridine(cas: 53939-30-3HPLC of Formula: 53939-30-3)

5-Bromo-2-chloropyridine(cas: 53939-30-3) belongs to pyridine. Pyridine is very deactivated towards electrophilic substitution with respect to benzene. For this reason classical formylation, using methods such as the Gattermann or Vilsmeier reactions, are not generally successful. HPLC of Formula: 53939-30-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2018,Chen, Tie-Gen; Barton, Lisa M.; Lin, Yutong; Tsien, Jet; Kossler, David; Bastida, Inaki; Asai, Shota; Bi, Cheng; Chen, Jason S.; Shan, Mingde; Fang, Hui; Fang, Francis G.; Choi, Hyeong-wook; Hawkins, Lynn; Qin, Tian; Baran, Phil S. published 《Building C(sp3)-rich complexity by combining cycloaddition and C-C cross-coupling reactions》.Nature (London, United Kingdom) published the findings.Name: 5-Bromo-2-chloropyridine The information in the text is summarized as follows:

Prized for their ability to rapidly generate chem. complexity by building new ring systems and stereocentres, cycloaddition reactions have featured in numerous total syntheses and are a key component in the education of chem. students. Similarly, carbon-carbon (C-C) cross-coupling methods are integral to synthesis because of their programmability, modularity and reliability. Within the area of drug discovery, an overreliance on cross-coupling has led to a disproportionate representation of flat architectures that are rich in carbon atoms with orbitals hybridized in an sp2 manner. Despite the ability of cycloadditions to introduce multiple carbon sp3 centers in a single step, they are less used. This is probably because of their lack of modularity, stemming from the idiosyncratic steric and electronic rules for each specific type of cycloaddition Here we demonstrate a strategy for combining the optimal features of these two chem. transformations into one simple sequence, to enable the modular, enantioselective, scalable and programmable preparation of useful building blocks, natural products and lead scaffolds for drug discovery. The results came from multiple reactions, including the reaction of 5-Bromo-2-chloropyridine(cas: 53939-30-3Name: 5-Bromo-2-chloropyridine)

5-Bromo-2-chloropyridine(cas: 53939-30-3) belongs to pyridine. Pyridine is very deactivated towards electrophilic substitution with respect to benzene. For this reason classical formylation, using methods such as the Gattermann or Vilsmeier reactions, are not generally successful. Name: 5-Bromo-2-chloropyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2018,Zhang, Yue-Mei; Greco, Michael N.; Macielag, Mark J.; Teleha, Christopher A.; DesJarlais, Renee L.; Tang, Yuting; Ho, George; Hou, Cuifen; Chen, Cailin; Zhao, Shuyuan; Kauffman, Jack; Camacho, Raul; Qi, Jenson; Murray, William; Demarest, Keith; Leonard, James published 《6-Benzhydryl-4-amino-quinolin-2-ones as Potent Cannabinoid Type 1 (CB1) Receptor Inverse Agonists and Chemical Modifications for Peripheral Selectivity》.Journal of Medicinal Chemistry published the findings.Category: pyridine-derivatives The information in the text is summarized as follows:

A novel series of 6-benzhydryl-4-amino-quinolin-2-ones was discovered as cannabinoid type 1 receptor (CB1R) inverse agonists based on the high-throughput screening hit, compound 1a. Structure-activity relationships were studied to improve in vitro/in vivo pharmacol. and restrict distribution to the peripheral circulation. We adopted several strategies such as increasing topol. polar surface area, incorporating discrete polyethylene glycol side chains, and targeting P-glycoprotein (P-gp) to minimize access to the brain. Compound 6a is a P-gp substrate and a potent and highly selective CB1R inverse agonist, demonstrating excellent in vivo metabolic stability and a low brain to plasma ratio. However, brain receptor occupancy studies showed that compound 6a may accumulate in brain with repeat dosing. This was evidenced by compound 6a inhibiting food intake and inducing weight loss in diet-induced obese mice. Thus, a strategy based on P-gp efflux may not be adequate for peripheral restriction of the disclosed quinolinone series. The results came from multiple reactions, including the reaction of 5-Bromo-2-chloropyridine(cas: 53939-30-3Category: pyridine-derivatives)

5-Bromo-2-chloropyridine(cas: 53939-30-3) belongs to pyridine. Pyridine’s structure is isoelectronic with that of benzene, but its properties are quite different. Pyridine is completely miscible with water, whereas benzene is only slightly soluble. Like all hydrocarbons, benzene is neutral (in the acid–base sense), but because of its nitrogen atom, pyridine is a weak base.Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2017,Wagman, Allan S.; Boyce, Rustum S.; Brown, Sean P.; Fang, Eric; Goff, Dane; Jansen, Johanna M.; Le, Vincent P.; Levine, Barry H.; Ng, Simon C.; Ni, Zhi-Jie; Nuss, John M.; Pfister, Keith B.; Ramurthy, Savithri; Renhowe, Paul A.; Ring, David B.; Shu, Wei; Subramanian, Sharadha; Zhou, Xiaohui A.; Shafer, Cynthia M.; Harrison, Stephen D.; Johnson, Kirk W.; Bussiere, Dirksen E. published 《Synthesis, Binding Mode, and Antihyperglycemic Activity of Potent and Selective (5-Imidazol-2-yl-4-phenylpyrimidin-2-yl)[2-(2-pyridylamino)ethyl]amine Inhibitors of Glycogen Synthase Kinase 3》.Journal of Medicinal Chemistry published the findings.Reference of 2-(2-Hydroxyethyl)pyridine The information in the text is summarized as follows:

In an effort to identify new antidiabetic agents, we have discovered a novel family of (5-imidazol-2-yl-4-phenylpyrimidin-2-yl)[2-(2-pyridylamino)ethyl]amine analogs which are inhibitors of human glycogen synthase kinase 3 (GSK3). We developed efficient synthetic routes to explore a wide variety of substitution patterns and convergently access a diverse array of analogs. Compound I (CHIR-911, CT-99021, or CHIR-73911) emerged from an exploration of heterocycles at the C-5 position, Ph groups at C-4, and a variety of differently substituted linker and aminopyridine moieties attached at the C-2 position. These compounds exhibited GSK3 IC50s in the low nanomolar range and excellent selectivity. They activate glycogen synthase in insulin receptor-expressing CHO-IR cells and primary rat hepatocytes. Evaluation of lead compounds I and II (CHIR-611 or CT-98014) in rodent models of type 2 diabetes revealed that single oral doses lowered hyperglycemia within 60 min, enhanced insulin-stimulated glucose transport, and improved glucose disposal without increasing insulin levels. The results came from multiple reactions, including the reaction of 2-(2-Hydroxyethyl)pyridine(cas: 103-74-2Reference of 2-(2-Hydroxyethyl)pyridine)

2-(2-Hydroxyethyl)pyridine(cas: 103-74-2) belongs to pyridine. Pyridines form stable salts with strong acids. Pyridine itself is often used to neutralize acid formed in a reaction and as a basic solvent. Reference of 2-(2-Hydroxyethyl)pyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem