154822-66-9

Upstream product

• 10557-85-4 4-iodo-3,5-dimethylisoxazole 
• 5720-07-0 4-methoxyphenylboronic acid 
• 79-24-3 Nitroethane 
• 123-11-5 4-methoxy-benzaldehyde 
• 1160169-36-7 1-(2-(4-methoxyphenyl)-3-methyl-2H-azirin-2-yl)ethanone 
• 300-87-8 3,5-dimethyl-1,2-oxazole 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 10558-25-5 4-bromo-3,5-dimethyl-1,2-oxazole 
• 105-13-5 4-Methoxybenzyl alcohol 
• 171364-79-7 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1160169-22-1 (Z)-4-amino-3-(4-methoxyphenyl)pent-3-en-2-one 
• 72969-10-9 3-(4'-methoxyphenyl)-pentane-2,4-dione 

Downstream Products

• 1355554-31-2 N-cyclopentyl-5-(3,5-dimethylisoxazol-4-yl)-2-methoxybenzenesulfonamide 
• 1355554-13-0 N-cyclopentyl-5-(3,5-dimethylisoxazol-4-yl)-2-hydroxybenzenesulfonamide 
• 1227693-30-2 5-(3,5-dimethylisoxazol-4-yl)-2-methoxybenzene-1-sulfonyl chloride 
• 1355770-63-6 (rac)-5-(3,5-dimethylisoxazol-4-yl)-2-methoxy-N-(piperidin-3-yl) benzenesulfonamide hydrochloride 
• 1355555-63-3 5-(3,5-dimethylisoxazol-4-yl)-2-methoxy-N-(piperidin-4-yl)benzenesulfonamide hydrochloride 
• 1355770-59-0 4-(4-methoxy-3-(piperazin-1-ylsulfonyl)phenyl)-3,5-dimethylisoxazole 
• 132572-89-5 3-(4-Methoxyphenyl)pentane-2,4-dione 

Relevant academic research and scientific papers

Simple Synthesis of Symmetrical 4-Substituted 3,5-Dialkylisoxazoles

A number of symmetrical 4-substituted 3,5-dialkylrsoxazoles have been prepared by treatment of aromatic aldehydes with nitroalkanes and aqueous sodium hydroxide.

The direct C(sp2)-H functionalization and coupling of aromatic N-heterocycles with (hetero)aryl bromides by [PdX2(imidazolidin-2-ylidene)(Py)] catalysts

In this study, a series of air- and moisture-stable imidazolidin-2-ylidene-based new palladium complexes with the general formula [PdX2(NHC)(Py)] were synthesized (NHC = N-heterocyclic carbene, Py = pyridine, X = Cl or I). The structures of the

Design, synthesis, and biological activity evaluation of a series of novel sulfonamide derivatives as BRD4 inhibitors against acute myeloid leukemia

Accumulating researches have contributed much effect to discover novel chemotherapeutic drug for leukemia with expeditious curative effect, of which bromodomain-containing protein 4 (BRD4) inhibitor is considered as a eutherapeutic drug which has presented efficient cell proliferation suppression effect. In this study, we disclosed a series of phenylisoxazole sulfonamide derivatives as potent BRD4 inhibitors. Especially, compound 58 exhibited robust inhibitory potency toward BRD4-BD1 and BRD4-BD2 with IC50 values of 70 and 140 nM, respectively. In addition, compound 58 significantly suppressed cell proliferation of leukemia cell lines HL-60 and MV4-11 with IC50 values of 1.21 and 0.15 μM. In-depth study of the biological mechanism of compound 58 exerted its tumor suppression effect via down-regulating the level of oncogene c-myc. Moreover, in vivo pharmacokinetics (PK) study was conducted and the results demonstrated better pharmacokinetics features versus (+)-JQ1. In summary, our study discovers that compound 58 represents as a novel BRD4 inhibitor for further investigation in development of leukemia inhibitor with potentiality.

The direct C4-arylation of 3,5-dimethylisoxazole with aryl bromides catalyzed by imidazolidin-2-ylidene based palladium-PEPPSI complexes

In this study, the synthesis and characterization of four new imidazolinium salts as carbene precursors and their corresponding four new PEPPSI-type (PEPPSI = .Pyridine Enhanced Precatalyst Preparation Stabilization and Initiation) palladium complexes wer

Ferrocenyl palladacycles derived from unsymmetrical pincer-type ligands: Evidence of Pd(0) nanoparticle generation during the Suzuki-Miyaura reaction and applications in the direct arylation of thiazoles and isoxazoles

A new family of ferrocenyl-palladacycle complexes Pd(L1)Cl (Pd1) and Pd(L2)Cl (Pd2) were synthesized and characterized by UV-visible, IR, ESI-MS, and NMR spectral studies. The molecular structures of Pd1 and Pd2 were determined by X-ray crystallographic studies. Palladacycle catalyzed Suzuki-Miyaura cross-coupling reactions were investigated utilizing the derivatives of phenylboronic acids and substituted chlorobenzenes. Mechanistic investigation authenticated the generation of Pd(0) nanoparticles during the catalytic cycle and the nanoparticles were characterized by XPS, SEM and TEM analysis. Direct C-H arylation of thiazole and isoxazole derivatives employing these ferrocenyl-palladacycle complexes was examined. The reaction model for the arylation reaction implicating the in situ generation of Pd(0) nanoparticles was proposed.

Heterocyclic Allylsulfones as Latent Heteroaryl Nucleophiles in Palladium-Catalyzed Cross-Coupling Reactions

Heterocyclic sulfinates are effective reagents in palladium-catalyzed coupling reactions with aryl and heteroaryl halides, often providing high yields of the targeted biaryl. However, the preparation and purification of complex heterocylic sulfinates can be problematic. In addition, sulfinate functionality is not tolerant of the majority of synthetic transformations, making these reagents unsuitable for multistep elaboration. Herein, we show that heterocyclic allylsulfones can function as latent sulfinate reagents and, when treated with a Pd(0) catalyst and an aryl halide, undergo deallylation, followed by efficient desulfinylative cross-coupling. A broad range of allyl heteroarylsulfones are conveniently prepared, using several complementary routes, and are shown to be effective coupling partners with a variety of aryl and heteroaryl halides. We demonstrate that the allylsulfone functional group can tolerate a range of standard synthetic transformations, including orthogonal C- and N-coupling reactions, allowing multistep elaboration. The allylsulfones are successfully coupled with a variety of medicinally relevant substrates, demonstrating their applicability in demanding cross-coupling transformations. In addition, pharmaceutical agents crizotinib and etoricoxib were prepared using allyl heteroaryl sulfone coupling partners, further demonstrating the utility of these new reagents.

Exploring Green Solvents Associated to Pd/C as Heterogeneous Catalyst for Direct Arylation of Heteroaromatics with Aryl Bromides

Metal residues are certainly one of the major sources of contamination of products in metal-catalyzed direct arylation reactions. We found that the use of only 1 mol% of the heterogeneous catalyst Pd/C promotes very efficiently the direct arylations of most heteroaromatics. In the presence of this catalyst and potassium acetate as the base, the direct arylation of thiophenes, furans, pyrroles, thiazoles, imidazoles or isoxazoles, using aryl bromides as coupling partners, proceeds highly regioselectively and in moderate to very high yields. With several heteroarenes both electron-deficient and electron-rich aryl bromides were tolerated; moreover, with the most reactive heteroarenes, the Pd/C catalyst tolerated green solvents such as diethyl carbonate, 3-methylbutan-1-ol and pentan-1-ol, affording a synthetic scheme with low environmental impact. (Figure presented.).

Highly Site Selective Formal [5+2] and [4+2] Annulations of Isoxazoles with Heterosubstituted Alkynes by Platinum Catalysis: Rapid Access to Functionalized 1,3-Oxazepines and 2,5-Dihydropyridines

Platinum-catalyzed formal [5+2] and [4+2] annulations of isoxazoles with heterosubstituted alkynes enabled the atom-economical synthesis of valuable 1,3-oxazepines and 2,5-dihydropyridines, respectively. Importantly, this Pt catalysis not only led to unique reactivity dramatically divergent from that observed under Au catalysis, but also proceeded via unprecedented α-imino platinum carbene intermediates.

Atom-Economic Synthesis of Fully Substituted 2-Aminopyrroles via Gold-Catalyzed Formal [3+2] Cycloaddition between Ynamides and Isoxazoles

A concise and flexible synthesis of fully substituted 2-aminopyrroles via gold-catalyzed formal [3+2] cycloaddition between ynamides and isoxazoles has been developed. Under mild reaction conditions, various 2-aminopyrrole derivatives were obtained in good to excellent yields, thus providing an efficient and atom-economic way for the construction of fully substituted 2-aminopyrroles. It was all very formal: A novel gold-catalyzed formal [3+2] cycloaddition between ynamides and isoxazoles has been developed, allowing the concise and flexible synthesis of fully substituted 2-aminopyrroles. Importantly, this strategy provides new mechanistic insights and offers an atom-economic way for the construction of fully substituted 2-aminopyrroles.

Highly functionalized biaryls via Suzuki-Miyaura cross-coupling catalyzed by Pd@MOF under batch and continuous flow regimes

A diverse set of more than 40 highly functionalized biaryls was synthesized successfully through the Suzuki-Miyaura cross-coupling reaction catalyzed by Pd nanoparticles supported in a functionalized mesoporous MOF (8 wt% Pd@MIL-101(Cr)-NH2). This could be achieved under some of the mildest conditions reported to date and a strong control over the leaching of metallic species could be maintained, despite the presence of diverse functional groups and/or several heteroatoms. Some of the targeted molecules are important intermediates in the synthesis of pharmaceuticals and we clearly exemplify the versatility of this catalytic system, which affords better yields than currently existing commercial procedures. Most importantly, Pd@MIL-101-NH2 was packed in a micro-flow reactor, which represents the first report of metallic nanoparticles supported on MOFs employed in flow chemistry for catalytic applications. A small library of 11 isolated compounds was created in a continuous experiment without replacing the catalyst, demonstrating the potential of the catalyst for large-scale applications.