Category: 791614-90-9

Chow, Wing-Kin published the artcilePalladium-Catalyzed Borylation of Aryl Mesylates and Tosylates and Their Applications in One-Pot Sequential Suzuki-Miyaura Biaryl Synthesis, Computed Properties of 791614-90-9, the publication is Chemistry – A European Journal (2011), 17(25), 6913-6917, S6913/1-S6913/47, database is CAplus and MEDLINE.

Palladium-catalyzed borylation with the N-methyl-2-(2′-dicyclohexylphosphino-5′-methoxyphenyl)indole (MeO-CM-Phos) ligand of ten aryl tosylates and twelve aryl mesylates gave the corresponding pinacol aryl boronates in 63% to 97% yield. The reaction conditions are mild and provide excellent functional-group compatibility (e.g., CN, CHO, COOMe, ketone, NH₂, benzodioxole, quinolyl, benzothiazole or NH-indole). E.g., reaction of 3-cyanophenyl mesylate with bis(pinacolato)diboron afforded pinacol (3-benzonitrile) boronate in 97% yield. The Pd/MeO-CM-phos catalyst system allows one-pot sequential reactions in the preparation of unsym. biaryls. Four biaryls were prepared by one-pot two-step and one-pot three-step transformations of aryl tosylates and 3-cyanophenol, resp.

Chemistry – A European Journal published new progress about 791614-90-9. 791614-90-9 belongs to thiazole, auxiliary class Boronate Esters,Boronic acid and ester,Boronic acid and ester, name is 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole, and the molecular formula is C14H18BNO2S, Computed Properties of 791614-90-9.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Zhang, Peng published the artcileStructure-activity relationships in a novel series of 7-substituted-aryl quinolines and 5-substituted-aryl benzothiazoles at the metabotropic glutamate receptor subtype 5, COA of Formula: C14H18BNO2S, the publication is Bioorganic & Medicinal Chemistry (2010), 18(9), 3026-3035, database is CAplus and MEDLINE.

The metabotropic glutamate receptor subtype 5 (mGluR5) has been implicated in numerous neuropsychiatric disorders including addiction. We have discovered that the rigid diaryl alkyne template, derived from the potent and selective noncompetitive mGluR5 antagonist 2-methyl-6-(phenylethynyl)pyridine (MPEP), can serve to guide the design of novel quinoline analogs and pharmacophore optimization has resulted in potent mGluR5 noncompetitive antagonists (EC₅₀ range 60-100 nM) in the quinoline series.

Bioorganic & Medicinal Chemistry published new progress about 791614-90-9. 791614-90-9 belongs to thiazole, auxiliary class Boronate Esters,Boronic acid and ester,Boronic acid and ester, name is 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole, and the molecular formula is C65H82N2O18S2, COA of Formula: C14H18BNO2S.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Kulkarni, Santosh S. published the artcileDiscovery of heterobicyclic templates for novel metabotropic glutamate receptor subtype 5 antagonists, Synthetic Route of 791614-90-9, the publication is Bioorganic & Medicinal Chemistry Letters (2007), 17(11), 2987-2991, database is CAplus and MEDLINE.

Investigation of a series of heterobicyclic compounds with essential pharmacophoric features of the metabotropic glutamate receptor 5 (mGluR5) antagonists MPEP and MTEP provided novel structural templates with sub-micromolar affinities at the mGluR5. Compound I showed antagonist activity (IC₅₀ = 0.26 μM) in the functional assay measuring hydrolysis of phosphoinositide and may provide a new lead for further SAR investigation.

Bioorganic & Medicinal Chemistry Letters published new progress about 791614-90-9. 791614-90-9 belongs to thiazole, auxiliary class Boronate Esters,Boronic acid and ester,Boronic acid and ester, name is 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole, and the molecular formula is C14H18BNO2S, Synthetic Route of 791614-90-9.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

He, Zhi-Tao published the artcileTrimethylphosphate as a Methylating Agent for Cross Coupling: A Slow-Release Mechanism for the Methylation of Arylboronic Esters, Application In Synthesis of 791614-90-9, the publication is Journal of the American Chemical Society (2018), 140(49), 17197-17202, database is CAplus and MEDLINE.

Tri-Me phosphate acted as an effective source of Me groups; in the presence of CuI, and LiI, (MeO)₃P(:O) underwent chemoselective coupling with arylpinacolboronates mediated by LiOt-Bu in 1,3-dimethylimidazolidin-2-one (DMI) to yield methylarenes in higher yields than related coupling reactions using either Me iodide or Me tosylate. The methylation reaction was used in tandem with iridium-catalyzed regioselective borylation with bis(pinacolato)diboron to provide a one-pot methylation reaction for arenes, and for trideuteromethylation of arylpinacoboronates using tris(trideuteromethyl) phosphate. The chemoselectivity of the reaction was tested using additives possessing various functional groups (robustness screen); unprotected amines, alcs., and amides and terminal alkynes were not tolerated. The methylation of 1-naphthylpinacolboronate was demonstrated on a 200 mmol scale. The kinetics of the methylation and its dependence on Li⁺ and I^– ions was determined and a mechanism suggested. Me iodide is released slowly upon reaction of tri-Me phosphate with iodide; the low concentration of MeI enables selective reaction with arylcopper intermediates generated from the arylboronate rather than with other nucleophiles, while binding of tert-butoxide to the pinacolboronate reactants inhibits reaction of MeI with tert-butoxide.

Journal of the American Chemical Society published new progress about 791614-90-9. 791614-90-9 belongs to thiazole, auxiliary class Boronate Esters,Boronic acid and ester,Boronic acid and ester, name is 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole, and the molecular formula is C14H18BNO2S, Application In Synthesis of 791614-90-9.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Wang, Xin published the artcileA Monophosphine Ligand Derived from Anthracene Photodimer: Synthetic Applications for Palladium-Catalyzed Coupling Reactions, Formula: C14H18BNO2S, the publication is Organic Letters (2019), 21(20), 8158-8163, database is CAplus and MEDLINE.

Herein, we present an air-stable dianthracenyl monophosphine ligand (diAnthPhos) which can be prepared in two steps from com. available anthracene derivatives The ligand exhibits excellent efficiency for palladium-catalyzed coupling reactions. In particular, Miyaura borylation of heterocycle-containing electrophiles can be facilitated employing the diAnthPhos ligand with a broad substrate scope and low catalyst loading. The valuable synthetic utility of the new ligand is further demonstrated by a one-pot Miyaura borylation/Suzuki coupling protocol for heteroaryl-containing substrates.

Organic Letters published new progress about 791614-90-9. 791614-90-9 belongs to thiazole, auxiliary class Boronate Esters,Boronic acid and ester,Boronic acid and ester, name is 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole, and the molecular formula is C16H10O5, Formula: C14H18BNO2S.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Zhao, Haiwei published the artcile[Ph₄P]⁺[Cu(CF₂H)₂]^–: A Powerful Difluoromethylating Reagent Inspired by Mechanistic Investigation, Category: thiazole, the publication is Angewandte Chemie, International Edition (2022), 61(42), e202210151, database is CAplus and MEDLINE.

The quest of the active species in copper-mediated difluoromethylation of aryl halides led to the discovery of a powerful difluoromethylating reagent [Ph₄P]⁺[Cu(CF₂H)₂]^–. [Ph₄P]⁺[Cu(CF₂H)₂]^– complex was able to difluoromethylate a variety of electrophiles including electron-deficient and electron-rich aryl iodides, heteroaryl iodides, activated heteroaryl bromides, chloride and aryl bromides with a directing group, as well as other electrophiles such as alkenyl iodide, benzyl bromides, allyl bromides, alkyl iodide, allyl carbonates and acid chloride. In addition, in the presence of an oxidant, [Ph₄P]⁺[Cu(CF₂H)₂]^– complex reacted with various lithium nbutyl arylboronic acid pinacol esters, alkyne and heteroarene. Moreover, [Ph₄P]⁺[Cu(CF₂H)₂]^– complex could transmetalate the difluoromethyl reagent to other metals such as [Ph₄P]⁺[CuCl₂]^– complex and [(DPPF)PdCl₂].

Angewandte Chemie, International Edition published new progress about 791614-90-9. 791614-90-9 belongs to thiazole, auxiliary class Boronate Esters,Boronic acid and ester,Boronic acid and ester, name is 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole, and the molecular formula is C14H14N2O2, Category: thiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica