Tag: 200-300

Preparation of some substituted 2,6-bis(2-pyridyl)pyridines was written by Case, Francis H.;Kasper, Thomas J.. And the article was included in Journal of the American Chemical Society in 1956.Recommanded Product: 2-Bromo-4-phenylpyridine This article mentions the following:

The appropriate 2- or 4-substituted pyridine (1 mole), 1.18 moles NaNH₂, and 2.2 moles PhNMe₂ heated 6 hrs. at 150-60° (130-40° with 4-ethylpyridine), cooled, and poured into H₂O, the organic layer dried, the PhNMe₂ distilled, and the residue distilled or recrystallized gave the corresponding substituted-2-aminopyridine (I) (substituent, % yield, and m.p. given): 4-Et, 53, 70-1° (from pert. ether); 4-Ph, 53, 164-5° (from C₆H₆); 6-Ph, 70, 71-2° (from petr. ether). The appropriate I (0.3 mole) in 175 cc. 48% HBr treated with 42 cc. Br, the mixture treated gradually with 52 g. NaNO₂ in 74 cc. H₂O below 5° and then with 112 g. NaOH in 285 cc. H₂O below 20°, and extracted with Et₂O, the extract evaporated, and the residue distilled in vacuo or recrystd, gave the corresponding substituted-2-bromopyridines (II) (substituent, % yield, and b.p./mm. or m.p. given): 4-Et, 88, 103-5°/11; 4-Ph, 63, 65-6° (from petr. ether); 6-Ph, 62, 51-2° (from petr. ether). The appropriate II (1 mole) and 1.1 moles CuCN heated gently with a smoky flame to beginning reaction, the mixture evacuated as quickly as possible to 5 mm. (40 mm. with the Me derivative), and the reaction product distilled rapidly gave the corresponding substituted-2-cyanopyridine (substituent, % yield, and m.p. given): 4-Me (III), 28, 88-9°; 4-Ph (IV), 60, 99-100°; 6-Ph (IVa), 67, 64-6°; 4-Et (V), 61, -(b₁₁ 123-4°). III (11.8 g.) in 125 cc. dry C₆H₆ and 100 cc. Et₂O treated with MeMgI from 35.5 g. MeI and 6 g. Mg in Et₂O, the mixture warmed to room temperature, stirred 1 hr., and decomposed with cold aqueous NH₄Cl, and the Et₂O layer worked up yielded 8.0 g. 2-acetyI-4-methylpyridine (VI), b₁₅ 95-7°, m. 33-4° (from petr. ether). V (13.2 g.) gave similarly 7.0 g. 4-Et homolog of VI. IVa (20 g.) refluxed 5 hrs. with 220 cc. saturated alc. HCl, cooled, filtered, concentrated in vacuo on the steam bath, cooled, poured into H₂O, and neutralized with NH₄OH precipitated 79% 2-carbethoxy-6-phenylpyridine (VII), colorless solid, m. 50-7°. IV (17.3 g.) yielded similarly 15.8 g. 4-Ph isomer (VIII) of VII, m. 60-1° (from petr. ether). VII (20 g.) and 14 g. dry EtOAc added with stirring to 9.2 g. NaOEt in 125 cc. dry C₆H₆, the mixture refluxed 21 hrs. with stirring, cooled, poured into 4.4 g. NaOH in 90 cc. H₂O, and the Et₂O layer worked up gave 9.3 g. 2-acetyl-6-phenylpyridine (IX), m. 75-6° (from petr. ether). VIII (14.5 g.) gave similarly 7.5 g. 4-Ph isomer of IX, m. 75-6°. 2-Bromo-4-phenylpyridine (6 g.) and 6 g. Cu powder in 12 g. Ph₂ heated 3 hrs. with stirring at 250° the mixture finely powdered and extracted with concentrated HCl, the acid solution basified with aqueous NaOH-NH₄OH and extracted with Et₂O, and the extract worked up gave 0.7 g. 4,4′-diphenyl-2,2′-bipyridine (X), m. 187-8°. 2-Bromo-4-ethylpyridine (28 g.) and 43.5 g. Cu powder heated 1 hr. at 200-20° and worked up in the usual manner gave 4.0 g. di-Et analog (XI) of X, colorless liquid, b_0.3 147-50°. XI in Et₂O treated with dry HCl gave XI.2HCl, m. 193-5° (from EtOH-Me₂CO). The appropriate 2-acetylpyridine or -quinoline (not over 5 g., 2.2 molar proportions), 1 mole BzH, 0.3 mole NH₄OAc, and 9 moles 28% NH₄OH heated 5 hrs. in a sealed tube at 250°, and the product isolated with hot C₆H₆ gave the following 2,6-bis-substituted-2-pyridyl)-4-phenylpyridines (substituent, % yield, and m.p. given): 4-Me, 18, 328-9° (from C₆H₆); 4-Et, 16, 114-15° (from petr. ether); 6-Ph, 17, 190-1° (from petr. ether); 4-Ph, 21, 257-8° (from EtNO₂). 2,6Bis(2-quinolyl)-4-phenylpyridine, 18, 295-6° (from C₆H₆). In the experiment, the researchers used many compounds, for example, 2-Bromo-4-phenylpyridine (cas: 54151-74-5Recommanded Product: 2-Bromo-4-phenylpyridine).

2-Bromo-4-phenylpyridine (cas: 54151-74-5) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Recommanded Product: 2-Bromo-4-phenylpyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Design and synthesis of 1-aryl-5-anilinoindazoles as c-Jun N-terminal kinase inhibitors was written by Jiang, Rong;Frackowiak, Bozena;Shin, Youseung;Song, Xinyi;Chen, Weimin;Lin, Li;Cameron, Michael D.;Duckett, Derek R.;Kamenecka, Theodore M.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2013.Product Details of 89978-52-9 This article mentions the following:

Starting from a pyrazole HTS (high throughput screening) hit, a series of 1-aryl-1H-indazoles have been synthesized as JNK3 inhibitors with moderate selectivity against JNK1. SAR studies led to the synthesis of a double digital nanomolar JNK3 inhibitor (I) with good in vivo exposure. In the experiment, the researchers used many compounds, for example, Ethyl 2-bromoisonicotinate (cas: 89978-52-9Product Details of 89978-52-9).

Ethyl 2-bromoisonicotinate (cas: 89978-52-9) belongs to pyridine derivatives. Pyridine’s the lone pair does not contribute to the aromatic system but importantly influences the chemical properties of pyridine, as it easily supports bond formation via an electrophilic attack. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Product Details of 89978-52-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Measurement and correlation on solubility of acetaminophen in aqueous solutions of 1-octyl-3-methyl imidazolium bromide, 1-butyl-4-methyl pyridinium bromide and 1-octyl-4-methyl pyridinium bromide was written by Mehrdad, Abbas;Taeb, Sara;Ehsani-Tabar, Sahar;Hossein Miri, Amir. And the article was included in Journal of Chemical Thermodynamics in 2020.Electric Literature of C10H16BrN This article mentions the following:

Aqueous solubility of acetaminophen in the presence of 1-octyl-3-Me imidazolium bromide, 1-butyl-4-Me pyridinium bromide and 1-octyl-4-Me pyridinium bromide ionic liquid, as co-solvent was investigated at different temperatures and mass fraction of ionic liquid The obtained results reveal that the solubility of acetaminophen was increased by increasing temperature and concentration of ionic liquid Solubility of ACP was significantly increased when mass fraction of 1-octyl-3-Me imidazolium bromide and 1-octyl-4-Me pyridinium bromide reaches to more than 0.05. The possible reasons behind enhanced solubility of ACP in aqueous solution of ionic liquid are hydrophobic interaction and the formed micelles by cations of ionic liquid Thermodn. functions of dissolution were calculated by Van’t Hoff equation. The exptl. solubility of acetaminophen was correlated with the modified Wilson and the electrolyte-NRTL models as activity coefficient model. In the experiment, the researchers used many compounds, for example, 1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6Electric Literature of C10H16BrN).

1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Electric Literature of C10H16BrN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A facile synthesis of bromo-2-alkoxypyridines was written by Shiao, Min Jen;Tarng, Kai Yih. And the article was included in Heterocycles in 1990.HPLC of Formula: 13472-81-6 This article mentions the following:

Several bromo-2-methoxypyridines and bromo-2-(benzyloxy)pyridines were synthesized by the reaction of bromo-substituted 2-pyridones with alkyl halides in the presence of Ag₂CO₃ in benzene. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-2-hydroxypyridine (cas: 13472-81-6HPLC of Formula: 13472-81-6).

3,5-Dibromo-2-hydroxypyridine (cas: 13472-81-6) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.HPLC of Formula: 13472-81-6

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Ligand-Promoted Meta-C-H Arylation of Anilines, Phenols, and Heterocycles was written by Wang, Peng;Farmer, Marcus E.;Huo, Xing;Jain, Pankaj;Shen, Peng-Xiang;Ishoey, Mette;Bradner, James E.;Wisniewski, Steven R.;Eastgate, Martin D.;Yu, Jin-Quan. And the article was included in Journal of the American Chemical Society in 2016.Quality Control of (2-Chloro-pyridin-3-yl)-carbamic acid tert-butyl ester This article mentions the following:

The authors report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C-H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C-H arylation with heterocyclic aryl iodides as coupling partners is also realized for the first time using this ligand. The utility for this transformation for drug discovery is showcased by allowing the meta-C-H arylation of a lenalidomide derivative The first steps toward a silver-free protocol for this reaction are also demonstrated. In the experiment, the researchers used many compounds, for example, (2-Chloro-pyridin-3-yl)-carbamic acid tert-butyl ester (cas: 209798-48-1Quality Control of (2-Chloro-pyridin-3-yl)-carbamic acid tert-butyl ester).

(2-Chloro-pyridin-3-yl)-carbamic acid tert-butyl ester (cas: 209798-48-1) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Quality Control of (2-Chloro-pyridin-3-yl)-carbamic acid tert-butyl ester

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Asymmetric Hydrogenation of Azaindoles: Chemo- and Enantioselective Reduction of Fused Aromatic Ring Systems Consisting of Two Heteroarenes was written by Makida, Yusuke;Saita, Masahiro;Kuramoto, Takahiro;Ishizuka, Kentaro;Kuwano, Ryoichi. And the article was included in Angewandte Chemie, International Edition in 2016.Recommanded Product: 257937-08-9 This article mentions the following:

High enantioselectivity was achieved for the hydrogenation of azaindoles by using the chiral catalyst, which was prepared from [Ru(η³-methallyl)₂(cod)] and a trans-chelating bis(phosphine) ligand (PhTRAP). The dearomative reaction exclusively occurred on the five-membered ring, thus giving the corresponding azaindolines with up to 97:3 enantiomer ratio. In the experiment, the researchers used many compounds, for example, tert-Butyl (3-bromopyridin-4-yl)carbamate (cas: 257937-08-9Recommanded Product: 257937-08-9).

tert-Butyl (3-bromopyridin-4-yl)carbamate (cas: 257937-08-9) belongs to pyridine derivatives. In contrast to benzene, Pyridine’s electron density is not evenly distributed over the ring, reflecting the negative inductive effect of the nitrogen atom. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Recommanded Product: 257937-08-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Crystal structure, spectroscopic characterization and Hirshfeld surface analysis of trans-diaqua[2,5-bis(pyridin-4-yl)-1,3,4-oxadiazole]dithiocyanatonickel(II) was written by Rhoufal, Ferdaousse;Bentiss, Fouad;Guesmi, Salaheddine;Ketatni, El Mostafa;Saadi, Mohamed;El Ammari, Lahcen. And the article was included in Acta Crystallographica, Section E: Crystallographic Communications in 2019.Safety of 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole This article mentions the following:

The reaction of 2,5-bis(pyridin-4-yl)-1,3,4-oxadiazole (4-pox) and thiocyanate ions, used as co-ligand with nickel salt NiCl₂·6H₂O, produced the title complex, [Ni(NCS)₂(C₁₂H₈N₄O)₂(H₂O)₂]. The Ni^II atom is located on an inversion center and is octahedrally coordinated by four N atoms from two ligands and two pseudohalide ions, forming the equatorial plane. The axial positions are occupied by two O atoms of coordinated water mols. In the crystal, the mols. are linked into a three-dimensional network through strong O-H···N hydrogen bonds. Hirshfeld surface anal. was used to investigate the intermol. interactions in the crystal packing. In the experiment, the researchers used many compounds, for example, 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7Safety of 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole).

2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Reduced pyridines, namely tetrahydropyridines, dihydropyridines and piperidines, are found in numerous natural and synthetic compounds. The synthesis and reactivity of these compounds have often been driven by the fact many of these compounds have interesting and unique pharmacological properties. Safety of 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Ring transformations in reactions of heterocyclic halo compounds with nucleophiles. XII. Action of potassium amide on 2-bromo-and 2,6-dibromo-3-hydroxypyridine was written by Roelfsema, W. A.;Den Hertog, H. J.. And the article was included in Tetrahedron Letters in 1967.Product Details of 6602-33-1 This article mentions the following:

2-Bromo-3-hydroxypyridine (I) was prepared from 3-ethoxy-2-nitropyridine. I treated 2 hrs. at -33° with an 8-fold molar amount of KNH2 in liquid NH3 yielded 85% pyrrole-2-carboxamide (II), m. 172.5-4.0°, also synthesized from pyrrole-2-carboxylic acid. Similarly 2,6-dibromo-3-hydroxypyridine, prepared from 3-hydroxypyridine, was converted to 80% 5-bromopyrrole-2-carboxamide, m. 136-8°. Apparently the conversion occurs without bond fission between C-2 and C-3 as in the analogous transformations of 3-amino-2-bromopyridine and 3-amino-2-bromoquinoline, but that the pyridine rings are broken between C-3 and C-4 atoms. A tentative reaction scheme for the conversion is given. In the experiment, the researchers used many compounds, for example, 2,6-Dibromo-3-hydroxypyridine (cas: 6602-33-1Product Details of 6602-33-1).

2,6-Dibromo-3-hydroxypyridine (cas: 6602-33-1) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Product Details of 6602-33-1

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Kinetics and mechanism of bromination of 2-pyridinone and related derivatives in aqueous solution was written by Tee, Oswald S.;Paventi, Martino. And the article was included in Journal of the American Chemical Society in 1982.Electric Literature of C5H3Br2NO This article mentions the following:

The tautomeric system 2-pyridone (I) ⇄ 2-hydroxypyridine (II) reacts with aqueous Br via the principal tautomer I at pH <6 and via the conjugate anion at pH >6. Attack upon I occurs preferentially at the 3 position, whereas reaction of the anion probably involves major attack at the 5 position. The facile dibromination of I results from the comparable reactivity of the monobromopyridones at pH <1 or pH >4. These conclusions are based upon kinetic and product studies of I bromination and various derivatives in aqueous solutions at pH 0-8. With respect to their reactivity toward Br, the pyridones behave as substituted phenoxide ions. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-2-hydroxypyridine (cas: 13472-81-6Electric Literature of C5H3Br2NO).

3,5-Dibromo-2-hydroxypyridine (cas: 13472-81-6) belongs to pyridine derivatives. Pyridine has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Electric Literature of C5H3Br2NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Novel fleximer pyrazole-containing adenosine analogues: chemical, enzymatic and highly efficient biotechnological synthesis was written by Khandazhinskaya, Anastasia;Eletskaya, Barbara;Fateev, Ilja;Kharitonova, Maria;Konstantinova, Irina;Barai, Vladimir;Azhayev, Alex;Hyvonen, Mervi T.;Keinanen, Tuomo A.;Kochetkov, Sergey;Seley-Radtke, Katherine;Khomutov, Alex;Matyugina, Elena. And the article was included in Organic & Biomolecular Chemistry in 2021.Computed Properties of C10H13BrN2O2 This article mentions the following:

Nucleoside analogs have long served as key chemotherapeutic drugs for the treatment of viral infections and cancers. Problems associated with the development of drug resistance have led to a search for the design of nucleosides capable of bypassing point mutations in the target enzyme’s binding site. As a possible answer to this, the Seley-Radtke group developed a flexible nucleoside scaffold (fleximers), where the heterocyclic purine base is split into its two components, i.e. pyrimidine and imidazole. Herein, we present a series of new pyrazole-containing flex-bases and the corresponding fleximer analogs of 8-aza-7-deaza nucleosides. Subsequent studies found that pyrazole-containing flex-bases are substrates of purine nucleoside phosphorylase (PNP). We have compared the chem. synthesis of fleximers and enzymic approaches with both isolated enzymes and the use of E. coli cells over-producing PNP. The latter provided stereochem. pure pyrazole-containing β-D-ribo- and β-D-2′-deoxyribo-fleximers and are beneficial in terms of environmental issues, are more economical, and streamline the steps required from a chem. approach. The reaction is carried out in water, avoiding hazardous chems., and the products are isolated by ion-exchange chromatog. using water/ethanol mixtures for elution. Moreover, the target nucleosides were obtained on a multi-milligram scale with >97-99% purity, and the reactions can be easily scaled up. In the experiment, the researchers used many compounds, for example, tert-Butyl (3-bromopyridin-4-yl)carbamate (cas: 257937-08-9Computed Properties of C10H13BrN2O2).

tert-Butyl (3-bromopyridin-4-yl)carbamate (cas: 257937-08-9) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Computed Properties of C10H13BrN2O2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem