223556-23-8

Upstream product

• 110-91-8 morpholine 
• 1073-67-2 4-vinylbenzyl chloride 
• 2351-50-0 4-iodostyrene 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 405-99-2 para-fluorostyrene 
• 1204-86-0 4-(4-morpholinyl)benzaldehyde 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 2768-02-7 (vinyl)trimethoxylsilane 
• 30483-75-1 4-bromophenyl-morpholine 

Downstream Products

• 1584730-48-2 1-(4-morpholinophenyl)-2-(phenylsilyl)ethane 
• 1401100-42-2 4-(4-(3-(5-nitrofuran-2-yl)-4,5-dihydroisoxazol-5-yl)phenyl)morpholine 

Relevant academic research and scientific papers

Copper-Catalyzed Transfer Hydrodeuteration of Aryl Alkenes with Quantitative Isotopomer Purity Analysis by Molecular Rotational Resonance Spectroscopy

A copper-catalyzed alkene transfer hydrodeuteration reaction that selectively incorporates one hydrogen and one deuterium atom across an aryl alkene is described. The transfer hydrodeuteration protocol is selective across a variety of internal and terminal alkenes and is also demonstrated on an alkene-containing complex natural product analog. Beyond using 1H, 2H, and 13C NMR analysis to measure reaction selectivity, six transfer hydrodeuteration products were analyzed by molecular rotational resonance (MRR) spectroscopy. The application of MRR spectroscopy to the analysis of isotopic impurities in deuteration chemistry is further explored through a measurement methodology that is compatible with high-throughput sample analysis. In the first step, the MRR spectroscopy signatures of all isotopic variants accessible in the reaction chemistry are analyzed using a broadband chirped-pulse Fourier transform microwave spectrometer. With the signatures in hand, measurement scripts are created to quantitatively analyze the sample composition using a commercial cavity enhanced MRR spectrometer. The sample consumption is below 10 mg with analysis times on the order of 10 min using this instrument - both representing order-of-magnitude reduction compared to broadband MRR spectroscopy. To date, these measurements represent the most precise spectroscopic determination of selectivity in a transfer hydrodeuteration reaction and confirm that product regioselectivity ratios of >140:1 are achievable under this mild protocol.

Nickel-Catalyzed Ligand-Free Hiyama Coupling of Aryl Bromides and Vinyltrimethoxysilane

We herein disclose the first Ni-catalyzed Hiyama coupling of aryl halides with vinylsilanes. This protocol uses cheap, nontoxic, and stable vinyltrimethoxysilane as the vinyl donor, proceeds under mild and ligand-free conditions, furnishing a diverse variety of styrene derivatives in high yields with excellent functional group compatibility.

COMPOUNDS AS MODULATORS OF TLR2 SIGNALING

The present disclosure relates to compounds, pharmaceutical compositions comprising such compounds, and use of such compounds in methods of treatment or in medicaments for treatment of inflammatory diseases and certain neurological disorders that are related to inflammatory signaling processes, including but not limited to misfolded proteins.

Synthesis and characterization of N-heterocyclic carbene-palladium(II) chlorides-1-methylindazole and -1-methylpyrazole complexes and their catalytic activity toward C-N coupling of aryl chlorides

A series of N-heterocyclic carbene-palladium(ii) chlorides-1-methylindazole and -1-methylpyrazole complexes was successfully synthesized and fully characterized by X-ray single crystal diffraction. In addition, initial investigations of their catalytic activity showed that they were efficient catalysts in the C-N coupling of primary and secondary amines with aryl chlorides at low catalyst loadings.

Iron-catalysed chemo-, regio-, and stereoselective hydrosilylation of alkenes and alkynes using a bench-stable iron(II) pre-catalyst

The chemo-, regio-, and stereoselective iron-catalysed hydrosilylation of alkenes and alkynes with excellent functional group tolerance is reported (34 examples, 41-96% yield). The catalyst and reagents are commercially available and easy to handle, with the active iron catalyst being generated in situ, thus providing a simple and practical methodology for iron-catalysed hydrosilylation. The silane products can be oxidised to the anti-Markovnikov product of olefin hydration, and the one-pot iron-catalysed hydrosilylation-oxidation of olefins to give silane(di)ols directly is also reported. The iron pre-catalyst was used at loadings as low as 0.07 mol%, and displayed catalyst turnover frequencies (TOF) approaching 60,000 molh-1. Initial mechanistic studies indicate an iron(I) active catalyst.

N-heterocyclic carbene-palladium(II)-4,5-dihydrooxazole complexes: Synthesis and catalytic activity toward amination of aryl chlorides

A series of novel N-heterocyclic carbene-palladium(II)-4,5-dihydrooxazole (NHC-PdII-Ox) complexes 3 were successfully synthesized from commercially available imidazolium salts 1, PdCl2, and 4,5-dihydrooxazoles 2 in a one-step process, and these complexes showed efficient catalytic activity toward the amination of aryl chlorides. Both secondary and primary amines were tolerated under the same reaction conditions. Under the optimal reaction conditions, the expected coupling products were obtained in moderate to high yields.

Antitubercular nitrofuran isoxazolines with improved pharmacokinetic properties

A series of tetracyclic nitrofuran isoxazoline anti-tuberculosis agents was designed and synthesized to improve the pharmacokinetic properties of an initial lead compound, which had potent anti-tuberculosis activity but suffered from poor solubility, high

Catalytic SNAr reaction of non-activated fluoroarenes with amines via Ru η6-arene complexes

Ru-catalyzed SNAr reaction of non-activated fluoroarenes with secondary amines proceeded through η6-arene complexes to give aminated products in up to 79% yield.

Synthesis, optimization and structure-activity relationships of 3,5-disubstituted isoxazolines as new anti-tuberculosis agents

In the course of the development of a potent series of nitrofuranylamide anti-tuberculosis agents, we investigated if the exceptional activity resulted in part from the isoxazoline core and if it possessed any intrinsic anti-tuberculosis activity. This led to the discovery of an isoxazoline ester with appreciable anti-tuberculosis activity. In this study we explored the anti-tuberculosis structure-activity relationship of the isoxazoline ester compound through systematic modification of the 3,5-di-substituted isoxazoline core. Two approaches were used: (i) modification of the potentially metabolically labile ester functionality at the 3 position with acids, amines, amides, reverse amides, alcohols, hydrazides, and 1,3,4-oxadiazoles; (ii) substitution of the distal benzyl piperazine ring in the 5 position of the isoxazoline ring with piperazyl-ureas, piperazyl-carbamates, biaryl systems, piperidines and morpholine. Attempts to replace the ester group at C-3 position of isoxazoline with a variety of bioisosteric head groups led to significant loss of the tuberculosis inhibition indicating that an ester is required for anti-tuberculosis activity. Optimization of the isoxazoline C-5 position produced compounds with improved anti-tuberculosis activity, most notably the piperazyl-urea and piperazyl-carbamate analogs.

Scope and utility of CsOH·H2O in animation reactions via direct coupling of aryl halides and sec-alcyclic amines

Direct coupling of aryl halides with sec-alicyclic amines promoted by CsOH·H2O in DMSO to the corresponding aryl substituted amines, with good to excellent yields, is reported herein. A variety of aryl halides and sec-alicyclic amines with a broad range of electronic diversity and functional groups was studied in this transformation, thus offering general applicability in organic synthesis.