Day: November 9, 2022

《Synthesis of Tridentate [1,2,4] Triazinyl-Pyridin-2-yl Indole Lewis Basic Complexants via Pd-Catalyzed Suzuki-Miyaura Cross-Couplingã€?was written by Gulledge, Zachary Z.; Tedder, Mariah L.; Lyons, Kyle R.; Carrick, Jesse D.. Synthetic Route of C5H3Br2NThis research focused ontriazinyl pyridinyl indole preparation; bromo triazinylpyridine indole boronicacid Suzuki Miyaura coupling palladium catalyst. The article conveys some information:

Full closure of the nuclear fuel cycle is predicated, in part, on defining efficient separations processes for the effective speciation of the neutron-absorbing lanthanides from the minor actinides post-PUREX. Pursuant to the aforementioned, a class of tridentate, Lewis basic procomplexants have been prepared leveraging a Pd-catalyzed Suzuki-Miyaura cross-coupling between 6-bromo-[1,2,4]-triazinylpyridine derivatives and various protected indole-boronic acids to afford functionalized 2-[6-(5,6-diphenyl-[1,2,4]triazin-3-yl)-pyridin-2-yl]-1H-indoles. A highly active catalyst/ligand system with low loadings was employed rapidly affording 26 examples in yields as high as 85%. Method optimization, substrate and indole scope, comparative anal. between coupling reagents, and a scale-up experiment are reported. The experimental part of the paper was very detailed, including the reaction process of 2,6-Dibromopyridine(cas: 626-05-1Synthetic Route of C5H3Br2N)

2,6-Dibromopyridine(cas: 626-05-1) belongs to pyridine. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Additionally, pyridine-based natural products continue to be discovered and studied for their properties and to understand their biosynthesis.Synthetic Route of C5H3Br2N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Visible-Light-Driven Dearomatization Reaction toward the Formation of Spiro[4.5]deca-1,6,9-trien-8-onesã€?was written by Dong, Wuheng; Yuan, Yao; Xie, Xiaomin; Zhang, Zhaoguo. Electric Literature of C33H24IrN3This research focused onvisible light dearomatization benzylbromomalonate alkyne; spirodecatrienone preparation. The article conveys some information:

A visible-light-driven regioselective dearomative cyclization between 2-benzyl-2-bromomalonate and alkynes under mild conditions leading to the formation of spiro[4,5]decanes has been developed. In the presence of H2O, a variety of 2-benzyl-2-bromomalonates smoothly undergo 5-exo-dig radical dearomative cyclization with alkynes to afford the corresponding spiro[4,5]decanes in moderate to good yield in a step-economical manner under oxidant-free conditions.fac-Tris(2-phenylpyridine)iridium(cas: 94928-86-6Electric Literature of C33H24IrN3) was used in this study.

fac-Tris(2-phenylpyridine)iridium(cas: 94928-86-6) belongs to pyridine. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Additionally, pyridine-based natural products continue to be discovered and studied for their properties and to understand their biosynthesis.Electric Literature of C33H24IrN3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Visible-Light-Mediated C-H Alkylation of Pyridine Derivativesã€?was written by Rammal, Fatima; Gao, Di; Boujnah, Sondes; Gaumont, Annie-Claude; Hussein, Aqeel A.; Lakhdar, Sami. Quality Control of 4-CyanopyridineThis research focused onvisible light alkylation pyridine derivative alkane. The article conveys some information:

We report herein a visible-light-mediated C-H alkylation of pyridine derivatives that proceeds by simple combination of a large variety of N-alkoxypyridinium ions with alkanes in the presence of 2 mol % of fac-Ir(ppy)3 under blue illumination. The mild reaction conditions together with the high group functional tolerance make of this process a useful synthetic platform for the construction of structurally strained heterocycles. Detailed mechanistic investigations, including d. functional theory calculations and quantum yield measurement, allowed us to understand factors controlling the reactivity and the selectivity of the reaction. The results came from multiple reactions, including the reaction of 4-Cyanopyridine(cas: 100-48-1Quality Control of 4-Cyanopyridine)

4-Cyanopyridine(cas: 100-48-1) belongs to pyridine. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Additionally, pyridine-based natural products continue to be discovered and studied for their properties and to understand their biosynthesis.Quality Control of 4-Cyanopyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Quality Control of 4,4′-Bis(chloromethyl)-2,2′-bipyridineOn March 1, 2019, Woo, Sung-Jun; Choi, Sunghan; Kim, So-Yoen; Kim, Pil Soo; Jo, Ju Hyoung; Kim, Chul Hoon; Son, Ho-Jin; Pac, Chyongjin; Kang, Sang Ook published an article in ACS Catalysis. The article was 《Highly Selective and Durable Photochemical CO2 Reduction by Molecular Mn(I) Catalyst Fixed on a Particular Dye-Sensitized TiO2 Platformã€? The article mentions the following:

A new Mn(I)-based hybrid system (OrgD-|TiO2|-MnP) for photocatalytic CO2 reduction is designed to be a co-assembly of Mn(4,4′-Y2-bpy)(CO)3Cl (MnP; Y = CH2PO(OH)2) and (E)-3-[5-(4-(diphenylamino)phenyl)-2,2′-bithiophen-2′-yl]-2-cyanoacrylicacid(OrgD) on TiO2 semiconductor particles. The OrgD-|TiO2|-MnP hybrid reveals persistent photocatalytic behavior, giving high turnover numbers and excellent product selectivity (HCOO- vs. CO) that surpass the catalytic activities of the related homogeneous and other heterogenized Mn photocatalytic systems reported so far. As a typical run, visible-light irradiation of the hybrid catalyst in the presence of 0.1M electron donor (ED) and 0.001M LiClO4 persistently produced HCOO- with a >99% selectivity accompanied by a trace amount of CO; the turnover number (TONformate) reached âˆ?10 after 25 h irradiation The product selectivity (HCOO-/CO) is controlled by changing the loading amount of MnP on the TiO2 surface. In-situ FTIR anal. of the hybrid during photocatalysis revealed that at low Mn concentration, the Mn-H monomeric mechanism associated with HCOO- formation is dominant, whereas at high Mn concentration, CO is formed via an Mn-Mn dimer mechanism. In the part of experimental materials, we found many familiar compounds, such as 4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4Quality Control of 4,4′-Bis(chloromethyl)-2,2′-bipyridine)

4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. Quality Control of 4,4′-Bis(chloromethyl)-2,2′-bipyridine Pyridine has a conjugated system of six π electrons that are delocalized over the ring.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Product Details of 138219-98-4On March 25, 2003, Peter, Katja; Thelakkat, Mukundan published an article in Macromolecules. The article was 《Synthesis and Characterization of Bifunctional Polymers Carrying Tris(bipyridyl)ruthenium(II) and Triphenylamine Unitsã€? The article mentions the following:

The synthesis, characterization, and properties of a highly soluble bifunctional polymer are described in which a tris(bipyridyl)Ru(II) unit acts as dye and triphenylamine units act as charge transport moieties. First a macro-ligand, a bipyridine carrying two poly(4-bromostyrene) chains, was synthesized by atom transfer radical polymerization (ATRP) of 4-bromostyrene in bulk using CuCl/PMDETA as the catalytic system and bis(chloromethyl) bipyridine as the initiator. The target polymer was then obtained via a polymer amination reaction in which the bromophenyl group was converted into a triphenylamine followed by metalation of the bipyridine unit of the macro-ligand with Ru(II) bis(bipyridine). The reaction conditions of ATRP and polymer amination reaction were optimized, and the degree of conversion for both steps was determined by gas chromatog. (GC) anal. of rest monomer content and elemental anal. of unreacted bromine, resp. The control in mol. weight was achieved maintaining a narrow distribution in the desired low mol. weight range of bulk polymerization of 4-bromostyrene. The polymer amination reaction using the Pd(OAc)2 and P(t-Bu)3 system was efficient, and the reaction was complete within 2 h. The metalation reaction could be followed by UV/vis spectroscopy. MALDI-TOF MS of the three polymers was carried out to obtain absolute mol. weights and their distribution. A comparison of these mol. weights gave addnl. information about the degree of polymer amination and metalation reaction. The thermal properties of the different polymers suggest that the thermal stability and the glass transition temperature increases from the starting macro-ligand which carries poly(4-bromostyrene) chains to the intermediate polymer having poly(vinyltriphenylamine) chains and finally to the bifunctional Ru(II) polymer complex. The results came from multiple reactions, including the reaction of 4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4Product Details of 138219-98-4)

4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4) belongs to pyridine derivatives. 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. Product Details of 138219-98-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Beccalli, Egle M.; Broggini, Gianluigi; Paladino, Giuseppe; Zoni, Caterina published an article in Tetrahedron. The title of the article was 《Palladium-mediated approach to dibenzo[b,e][1,4]diazepines and benzopyrido-analogues. An efficient synthesis of tarpaneã€?Recommanded Product: 1028-86-0 The author mentioned the following in the article:

An original synthetic route toward dibenzo[b,e][1,4]diazepin-11-ones, e.g., I, and analogs pyridobenzodiazepinones has been developed. The method relied upon an intramol. amination process between an (hetero)aryl halide and the appropriate aniline moiety. In the experimental materials used by the author, we found N-(2-Chloropyridin-3-yl)-2-nitrobenzamide(cas: 1028-86-0Recommanded Product: 1028-86-0)

N-(2-Chloropyridin-3-yl)-2-nitrobenzamide(cas: 1028-86-0) belongs to anime. To avoid the problem of multiple alkylation, methods have been devised for “blockingâ€?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.Recommanded Product: 1028-86-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 1968,Tetrahedron included an article by Pala, Gianfranco; Crescenzi, Elda; Bietti, G.. SDS of cas: 16985-07-2. The article was titled 《New synthesis of 4,4′-dihydroxydiphenyl(2-pyridyl)-methaneã€? The information in the text is summarized as follows:

Condensing phenol with 2-pyridine carboxaldehyde was shown to give 4,4′-dihydroxydiphenyl(2-pyridyl)methane (I) together with 24-29% of its isomer 2,4′-dihydroxydiphenyl(2-pyridyl)methane (II). Recrystallization of the mixture, required to obtain I free from II, caused the yield of I to fall to scarcely 25%, based on 2-pyridine carboxaldehyde. To prevent or reduce formation of ortho condensation products, 2-pyridine carboxaldehyde was made to react with phenols halo-substituted in both or in a single ortho position. Reductive dehalogenation of the compounds thus obtained gave I in 65-70% yield. The results came from multiple reactions, including the reaction of 2,2′-(Pyridin-2-ylmethylene)diphenol(cas: 16985-07-2SDS of cas: 16985-07-2)

2,2′-(Pyridin-2-ylmethylene)diphenol(cas: 16985-07-2) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. SDS of cas: 16985-07-2The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The author of 《Catalytic enantioselective borane reduction of benzyl oximes: preparation of (S)-1-pyridin-3-yl-ethylamine bis hydrochlorideã€?were Huang, Kun; Ortiz-Marciales, Margarita. And the article was published in Organic Syntheses in 2010. Quality Control of (S)-1-(Pyridin-3-yl)ethanamine dihydrochloride The author mentioned the following in the article:

The enantioselective preparation of (S)-1-(pyridin-3-yl)ethylamine bis hydrochloride is achieved by chiral spiroborate ester-catalyzed borane reduction of (E)-1-(pyridin-3-yl)ethanone O-benzyl-oxime in 88% yield, and 94% ee. In the part of experimental materials, we found many familiar compounds, such as (S)-1-(Pyridin-3-yl)ethanamine dihydrochloride(cas: 40154-84-5Quality Control of (S)-1-(Pyridin-3-yl)ethanamine dihydrochloride)

(S)-1-(Pyridin-3-yl)ethanamine dihydrochloride(cas: 40154-84-5) belongs to anime. Nitrous acid converts secondary amines (aliphatic or aromatic) to N-nitroso compounds (nitrosamines): R2NH + HNO2 â†?R2N―NO. Some nitrosamines are potent cancer-inducing substances, and their possible formation is a serious consideration when nitrites, which are salts of nitrous acid, are present in foods or pharmaceutical preparations. Tertiary amines give rise to nitrosamines more slowly; an alkyl group is eliminated as an aldehyde or ketone, along with nitrous oxide, N2O.Quality Control of (S)-1-(Pyridin-3-yl)ethanamine dihydrochloride

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2014,Lafaye, Kevin; Nicolas, Lionel; Guerinot, Amandine; Reymond, Sebastien; Cossy, Janine published 《Lewis Basicity Modulation of N-Heterocycles: A Key for Successful Cross-Metathesisã€?Organic Letters published the findings.Reference of 5-Bromo-2-chloropyridine The information in the text is summarized as follows:

Introducing a chloro or other substituent neighboring the nitrogen atom of azaheterocycle-containing alkenes decreased their Lewis basicity sufficiently that, in most cases, they underwent olefin cross-metathesis with alkenes such as Me acrylates and (Z)-2-butene-1,4-diol diacetate in the presence of the second-generation Hoveyda-Grubbs ruthenium metathesis catalyst to give azaheteroaryl-substituted alkenes diastereoselectively. A variety of electron-deficient and electron-rich olefins and styrenes underwent metathesis, while chloro-, bromo-, fluoro-, trifluoromethyl-, trifloxy-, methoxy-, and tert-butyl-substituted pyridinylalkenes and chloro-substituted pyrimidinyl, isoquinolinyl, imidazolyl, and pyrazolyl alkenes were effective metathesis substrates. The experimental process involved the reaction of 5-Bromo-2-chloropyridine(cas: 53939-30-3Reference of 5-Bromo-2-chloropyridine)

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.Reference of 5-Bromo-2-chloropyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2016,Hyde, Alan M.; Liu, Zhijian; Kosjek, Birgit; Tan, Lushi; Klapars, Artis; Ashley, Eric R.; Zhong, Yong-Li; Alvizo, Oscar; Agard, Nicholas J.; Liu, Guiquan; Gu, Xiuyan; Yasuda, Nobuyoshi; Limanto, John; Huffman, Mark A.; Tschaen, David M. published 《Synthesis of the GPR40 Partial Agonist MK-8666 through a Kinetically Controlled Dynamic Enzymatic Ketone Reductionã€?Organic Letters published the findings.Electric Literature of C5H3BrClN The information in the text is summarized as follows:

A scalable and efficient synthesis of the GPR40 agonist MK-8666 was developed from a simple pyridine building block. The key step to set the stereochem. at two centers relied on an enzymic dynamic kinetic reduction of an unactivated ketone. Directed evolution was leveraged to generate an optimized ketoreductase that provided the desired trans alc. in >30:1 dr and >99% ee. Further, it was demonstrated that all four diastereomers of this hydroxy-ester could be prepared in high yield and selectivity. Subsequently, a challenging intramol. displacement was carried out to form the cyclopropane ring system with perfect control of endo/exo selectivity. The endgame coupling strategy relied on a Pd-catalyzed C-O coupling to join the headpiece chloropyridine with the benzylic alc. tailpiece. After reading the article, we found that the author used 5-Bromo-2-chloropyridine(cas: 53939-30-3Electric Literature of C5H3BrClN)

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. Electric Literature of C5H3BrClN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem