Pyridine-derivatives

Zurwerra, Didier; Quetglas, Vincent; Kloer, Daniel P.; Renold, Peter; Pitterna, Thomas published an article in Organic Letters. The title of the article was 《Synthesis and Stability of Boratriazaroles》.Synthetic Route of C6H7BClNO2 The author mentioned the following in the article:

We describe the synthesis and stability anal. of novel boratriazaroles that can be viewed as bioisosteres of imidazoles or pyrazoles. These heterocycles could conveniently be obtained by condensing a boronic acid and amidrazone 1 in various solvents. A detailed stability anal. of selected compounds at different pH values as a function of time led to the identification of steric hindrance around the boron atom as a key element for stabilization. In addition to this study using (6-Chloro-5-methylpyridin-3-yl)boronic acid, there are many other studies that have used (6-Chloro-5-methylpyridin-3-yl)boronic acid(cas: 1003043-40-0Synthetic Route of C6H7BClNO2) was used in this study.

(6-Chloro-5-methylpyridin-3-yl)boronic acid(cas: 1003043-40-0) belongs to pyridine. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. As ligands, solvents, and catalysts they facilitate reactions; thus descriptions of these new ligands and their applications abound each year.Synthetic Route of C6H7BClNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2009,Butcher, Ken J.; Hurst, Jenny published 《Aromatic amines as nucleophiles in the Bargellini reaction》.Tetrahedron Letters published the findings.Related Products of 13534-97-9 The information in the text is summarized as follows:

Aromatic amines can be employed in the Bargellini condensation with piperidinone and CHCl3 in the presence of NaOH to generate useful intermediates. Rapid, practical access to functionalized, privileged structures may have utility in the synthesis of drug-like mols. An improved synthesis of carfentanil analogs illustrates this point. In the experiment, the researchers used many compounds, for example, 6-Bromopyridin-3-amine(cas: 13534-97-9Related Products of 13534-97-9)

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. Amine, any member of a family of nitrogen-containing organic compounds that is derived, either in principle or in practice, from ammonia (NH3). Naturally occurring amines include the alkaloids, which are present in certain plants; the catecholamine neurotransmitters (i.e., dopamine, epinephrine, and norepinephrine); and a local chemical mediator, histamine, that occurs in most animal tissues.Related Products of 13534-97-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2013,Sharma, Sushila; Kumar, Manoranjan; Kumar, Vishal; Kumar, Neeraj published 《Vasicine catalyzed direct C-H arylation of unactivated arenes: organocatalytic application of an abundant alkaloid》.Tetrahedron Letters published the findings.Application of 13534-97-9 The information in the text is summarized as follows:

Vasicine, a quinazoline alkaloid isolated from Adhatoda vasica, has been employed as an organocatalyst for direct C-H arylation of unactivated arenes with aryl iodides/bromides without the assistance of any transition metal catalyst. A number of sensitive functional groups such as Me, methoxy, O-benzyl, acetyl, and amino were well tolerated under present reaction conditions. Mechanistic investigation supported the involvement of radical intermediates.6-Bromopyridin-3-amine(cas: 13534-97-9Application of 13534-97-9) was used in this study.

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. To avoid the problem of multiple alkylation, methods have been devised for “blocking” substitution so that only one alkyl group is introduced. The Gabriel synthesis is one such method; it utilizes phthalimide, C6H4(CO)2NH, whose one acidic hydrogen atom has been removed upon the addition of a base such as KOH to form a salt.Application of 13534-97-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2013,Oberli, Matthias A.; Buchwald, Stephen L. published 《A General Method for Suzuki-Miyaura Coupling Reactions Using Lithium Triisopropyl Borates [Erratum to document cited in CA157:409485]》.Organic Letters published the findings.Electric Literature of C5H5BrN2 The information in the text is summarized as follows:

An NIH grant acknowledgment was omitted from the published article; the omitted acknowledgment is given. In the experiment, the researchers used many compounds, for example, 6-Bromopyridin-3-amine(cas: 13534-97-9Electric Literature of C5H5BrN2)

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. The methylamines occur in small amounts in some plants. Many polyfunctional amines (i.e., those having other functional groups in the molecule) occur as alkaloids in plants—for example, mescaline, 2-(3,4,5-trimethoxyphenyl)ethylamine; the cyclic amines nicotine, atropine, morphine, and cocaine; and the quaternary salt choline, N-(2-hydroxyethyl)trimethylammonium chloride, which is present in nerve synapses and in plant and animal cells.Electric Literature of C5H5BrN2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2013,Konze, Kyle D.; Ma, Anqi; Li, Fengling; Barsyte-Lovejoy, Dalia; Parton, Trevor; MacNevin, Christopher J.; Liu, Feng; Gao, Cen; Huang, Xi-Ping; Kuznetsova, Ekaterina; Rougie, Marie; Jiang, Alice; Pattenden, Samantha G.; Norris, Jacqueline L.; James, Lindsey I.; Roth, Bryan L.; Brown, Peter J.; Frye, Stephen V.; Arrowsmith, Cheryl H.; Hahn, Klaus M.; Wang, Gang Greg; Vedadi, Masoud; Jin, Jian published 《An Orally Bioavailable Chemical Probe of the Lysine Methyltransferases EZH2 and EZH1》.ACS Chemical Biology published the findings.Category: pyridine-derivatives The information in the text is summarized as follows:

EZH2 or EZH1 is the catalytic subunit of the polycomb repressive complex 2 that catalyzes methylation of histone H3 lysine 27 (H3K27). The trimethylation of H3K27 (H3K27me3) is a transcriptionally repressive post-translational modification. Overexpression of EZH2 and hypertrimethylation of H3K27 have been implicated in a number of cancers. Several selective inhibitors of EZH2 have been reported recently. Herein we disclose UNC1999, the first orally bioavailable inhibitor that has high in vitro potency for wild-type and mutant EZH2 as well as EZH1, a closely related H3K27 methyltransferase that shares 96% sequence identity with EZH2 in their resp. catalytic domains. UNC1999 was highly selective for EZH2 and EZH1 over a broad range of epigenetic and non-epigenetic targets, competitive with the cofactor SAM and non-competitive with the peptide substrate. This inhibitor potently reduced H3K27me3 levels in cells and selectively killed diffused large B cell lymphoma cell lines harboring the EZH2Y641N mutant. Importantly, UNC1999 was orally bioavailable in mice, making this inhibitor a valuable tool for investigating the role of EZH2 and EZH1 in chronic animal studies. We also designed and synthesized UNC2400, a close analog of UNC1999 with potency >1,000-fold lower than that of UNC1999 as a neg. control for cell-based studies. Finally, we created a biotin-tagged UNC1999 (UNC2399), which enriched EZH2 in pull-down studies, and a UNC1999-dye conjugate (UNC2239) for co-localization studies with EZH2 in live cells. Taken together, these compounds represent a set of useful tools for the biomedical community to investigate the role of EZH2 and EZH1 in health and disease. In the experiment, the researchers used 5-Bromo-2-chloropyridine(cas: 53939-30-3Category: pyridine-derivatives)

5-Bromo-2-chloropyridine(cas: 53939-30-3) 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. Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2014,Sharma, Sanjeev; Kim, Hyungjun; Lee, Young Hoon; Kim, Taewon; Lee, Yoon Sup; Lee, Min Hyung published 《Heteroleptic Cyclometalated Iridium(III) Complexes Supported by Triarylborylpicolinate Ligand: Ratiometric Turn-On Phosphorescence Response upon Fluoride Binding》.Inorganic Chemistry published the findings.Synthetic Route of C7H6BrNO2 The information in the text is summarized as follows:

Heteroleptic cyclometalated iridium(III) complexes (CN̂)2Ir(Bpic) (4-6) (CN̂ = dfppy (4), ppy (5), btp (6)) supported by triarylborylpicolinate (Bpic) ancillary ligand were synthesized and characterized. X-ray diffraction (XRD) study of 5 confirmed NÔ chelation of the Bpic ligand to the iridium center forming an (CN̂)2Ir-borane conjugate. While the UV/vis absorption bands of 4-6 remained almost unchanged in the low-energy region upon fluoride addition, a ratiometric turn-on phosphorescence response was observed for 4 and 5. In contrast, the phosphorescence of 6 was little affected by fluoride binding. Exptl. and theor. studies suggest that the LUMO in neutral 4 and 5 is dominated by the Bpic ligand, which makes the weakly emissive 3ML’CT/3LL’CT (L = CN̂; L’ = Bpic) states as the lowest-energy triplet excited state, while the fluoride binding to 4 and 5 induces the highly emissive 3MLCT/3ππ* states centered on the (CN̂)2Ir moiety. Thermally induced conversion from the 3MLCT/3ππ* to the 3ML’CT/3LL’CT states is suggested to be responsible for the low-energy weak phosphorescence in 4 and 5. In addition to this study using Methyl 5-bromopicolinate, there are many other studies that have used Methyl 5-bromopicolinate(cas: 29682-15-3Synthetic Route of C7H6BrNO2) was used in this study.

Methyl 5-bromopicolinate(cas: 29682-15-3) belongs to pyridine. Pyridine derivatives lend themselves to many roles in the spirited field of supramolecular chemistry – whether as the ligand backbone of metal-organic polymers or presiding over the key electronic stations of nanodevices. In biochemistry, pyridine-containing cofactors are necessary nutrients on which our lives depend. Synthetic Route of C7H6BrNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2016,Chapman, Michael R.; Kwan, Maria H. T.; King, Georgina E.; Kyffin, Benjamin A.; Blacker, A. John; Willans, Charlotte E.; Nguyen, Bao N. published 《Rapid, metal-free and aqueous synthesis of imidazo[1,2-a]pyridine under ambient conditions》.Green Chemistry published the findings.Category: pyridine-derivatives The information in the text is summarized as follows:

A novel, rapid and efficient route to imidazo[1,2-a]pyridines I [R = H, 7-CH3, 6-NO2, etc.] under ambient, aqueous and metal-free conditions was reported. The NaOH-promoted cycloisomerization of N-propargylpyridiniums gave quant. yield in a few minutes (10 g scale). A comparison of common green metrics to current routes showed clear improvements, with at least a one order of magnitude increase in space-time-yield. The experimental part of the paper was very detailed, including the reaction process of 2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8Category: pyridine-derivatives)

2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8) 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. Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2017,Bhatt, V. P.; Samant, S. D.; Pednekar, Suhas published 《Nucleophilic addition of arylmethylzinc reagents (ArCH2ZnCl) to formaldehyde: An easy access to 2-(hetero)arylethyl alcohols》.Synthetic Communications published the findings.Category: pyridine-derivatives The information in the text is summarized as follows:

The nucleophilic addition of benzyl zinc reagents derived from inexpensive and abundant benzyl chlorides to paraformaldehyde was reported. The reaction investigated herein is hitherto unknown and was found to be selective, operationally simple, atom- and step-economical and high yielding to deliver phenethyl alcs. utilized as key perfumery ingredients in 60-83% yields. After successful establishment of the reaction condition, the reaction was also scaled up successfully to deliver a large-scale preparation of the phenethyl alc.2-(2-Hydroxyethyl)pyridine(cas: 103-74-2Category: pyridine-derivatives) was used in this study.

2-(2-Hydroxyethyl)pyridine(cas: 103-74-2) 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.Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2017,Pang, Lijuan; Bezencon, Jacqueline; Kleeb, Simon; Rabbani, Said; Sigl, Anja; Smiesko, Martin; Sager, Christoph P.; Eris, Deniz; Schwardt, Oliver; Ernst, Beat published 《FimH antagonists – solubility vs. permeability》.Carbohydrate Chemistry published the findings.HPLC of Formula: 29682-15-3 The information in the text is summarized as follows:

Urinary tract infections (UTIs) caused by uropathogenic Escherichia coli (UPEC) are among the most prevalent infections worldwide. Since frequent antibiotic treatment favors the emergence of antibiotic resistance, efficient non-antibiotic strategies are urgently needed. The first step of the pathogenesis of UTI is the bacterial adherence to urothelial host cells, a process mediated by the mannose-binding adhesin FimH located at the tip of bacterial pili. In a preliminary study, biphenyl α-D-mannopyranosides with an electron-withdrawing carboxylate on the aglycon were identified as potent FimH antagonists. Although passive permeability could be established by masking the carboxylate as an ester, insufficient solubility and fast hydrolysis did not allow to maintain the therapeutic concentration in the bladder for the requested period of time. By modifying the substitution pattern, mol. planarity and symmetry of the biphenyl aglycon could be disrupted leading to improved solubility In addition, when heteroatoms were introduced to the aglycon, antagonists with further improved solubility, metabolic stability as well as passive permeability were obtained. The best representative, the pyrrolylphenyl mannoside 42f exhibited therapeutic urine concentration for up to 6 h and is therefore a promising oral candidate for UTI prevention and/or treatment. In the experiment, the researchers used Methyl 5-bromopicolinate(cas: 29682-15-3HPLC of Formula: 29682-15-3)

Methyl 5-bromopicolinate(cas: 29682-15-3) 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: 29682-15-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2018,ACS Catalysis included an article by Siddiki, S. M. A. Hakim; Touchy, Abeda S.; Jamil, A. R. Md.; Toyao, Takashi; Shimizu, Ken-ichi. Safety of 2-(2-Hydroxyethyl)pyridine. The article was titled 《C-Methylation of Alcohols, Ketones, and Indoles with Methanol Using Heterogeneous Platinum Catalysts》. The information in the text is summarized as follows:

A versatile, selective, and recyclable heterogeneous catalytic method for the methylation of C-H bonds in alcs., ketones, and indoles with methanol under oxidant-free conditions using a Pt-loaded carbon (Pt/C) catalyst in the presence of NaOH is reported. This catalytic system is effective for various methylation reactions: (1) the β-methylation of primary alcs., including aryl, aliphatic, and heterocyclic alcs., (2) the α-methylation of ketones, and (3) the selective C3-methylation of indoles. The reactions are driven by a borrowing-hydrogen mechanism. The reaction begins with the dehydrogenation of the alc.(s) to afford aldehydes, which subsequently undergo a condensation reaction with the nucleophile (aldehyde, ketone, or indole), followed by hydrogenation of the condensation product by Pt-H species to yield the desired product. In all of the methylation reactions explored in this study, the Pt/C catalyst exhibits a significantly higher turnover number than other previously reported homogeneous catalytic systems. Moreover, it is demonstrated that the high catalytic activity of Pt can be rationalized in terms of the adsorption energy of hydrogen on the metal surface, as revealed by d. functional theory calculations on different metal surfaces. The experimental part of the paper was very detailed, including the reaction process of 2-(2-Hydroxyethyl)pyridine(cas: 103-74-2Safety of 2-(2-Hydroxyethyl)pyridine)

2-(2-Hydroxyethyl)pyridine(cas: 103-74-2) belongs to pyridine. Pyridine is a relatively complex molecule and exhibits a number of different bands in IR spectra. Among others, the bands characterizing the ν8a and ν19b modes have been found to be sensitive to the coordination or protonation of the molecule. Note that the band that is diagnostic for the PyH+ ion at about 1545 cm− 1 (ν19b mode) does not overlap with any of the other bands.Safety of 2-(2-Hydroxyethyl)pyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem