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Usage

Uses

Used in Organic Synthesis:
4-Difluoromethoxyphenylboronic acid pinacol ester is used as a reagent in organic synthesis for its ability to participate in Suzuki-Miyaura cross-coupling reactions, which are crucial for constructing carbon-carbon bonds. This application is essential for the formation of complex organic molecules.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 4-Difluoromethoxyphenylboronic acid pinacol ester is employed as a building block for the synthesis of pharmaceutical compounds. Its unique properties allow for the creation of new drugs with improved efficacy and selectivity.
Used in Pharmaceutical Industry:
4-Difluoromethoxyphenylboronic acid pinacol ester is used as a key intermediate in the pharmaceutical industry for the development of new drugs. Its distinct fluorinated phenyl group can enhance the pharmacokinetic and pharmacodynamic properties of the resulting compounds, leading to more effective medications.
Used in Agrochemical Industry:
4-Difluoromethoxyphenylboronic acid pinacol ester is utilized as a precursor in the agrochemical industry for the synthesis of agrochemicals. Its versatility in cross-coupling reactions enables the production of a variety of agrochemicals with specific pesticidal or herbicidal properties.
Used in Materials Science:
In materials science, 4-Difluoromethoxyphenylboronic acid pinacol ester is used as a component in the development of new materials. Its unique structural features can contribute to the creation of materials with tailored properties for specific applications, such as in electronics or advanced composites.

InChI:InChI=1/C13H17BF2O3/c1-12(2)13(3,4)19-14(18-12)9-5-7-10(8-6-9)17-11(15)16/h5-8,11H,1-4H3

Upstream product

• 22236-10-8 4-difluoromethoxyaniline 
• 73183-34-3 bis(pinacol)diborane 
• 333-27-7 methyl trifluoromethanesulfonate 
• 458-92-4 (difluoromethoxy)benzene 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 5905-69-1 1-bromo-4-(difluoromethoxy)benzene 
• 106-41-2 4-bromo-phenol 
• 5419-55-6 Triisopropyl borate 
• 109-72-8 n-butyllithium 
• 128140-82-9 1-(difluoromethoxy)-4-iodobenzene 

Downstream Products

• 1123178-21-1 2-chloro-5-(4-(difluoromethoxy)phenyl)pyrimidine 
• 1123512-30-0 N-(4-(2-(diethylamino)ethoxy)phenyl)-5-(4-(difluoromethoxy)phenyl)pyrimidin-2-amine 
• 1123512-36-6 1-(4-((5-(4-(difluoromethoxy)phenyl)pyrimidin-2-yl)-amino)benzyl)piperidine-4-carboxylic acid 
• 1123515-81-0 methyl 1-(2-(5-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)-2-fluorophenoxy)ethyl)piperidine-4-carboxylate 
• 1123512-43-5 1-(4-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenethyl)piperidine-4-carboxylic acid 
• 1123515-34-3 2-(4-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenyl)-3-hydroxypropanoic acid 
• 1123515-38-7 5-(4-(difluoromethoxy)phenyl)-N-(4-methyl-3-nitrophenyl)pyrimidin-2-amine 
• 1354286-48-8 N-(5-(4-(difluoromethoxy)phenyl)-2-morpholinopyridin-4-yl)-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine 
• 31408-23-8 5-phenyl-pyrimidin-2-ylamine 

Relevant academic research and scientific papers

Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds

Boronic acids are centrally important functional motifs and synthetic precursors. Visible light-induced borylation may provide access to structurally diverse boronates, but a broadly efficient photocatalytic borylation method that can effect borylation of a wide range of substrates, including strong C-O bonds, remains elusive. Herein, we report a general, metal-free visible light-induced photocatalytic borylation platform that enables borylation of electron-rich derivatives of phenols and anilines, chloroarenes, as well as other haloarenes. The reaction exhibits excellent functional group tolerance, as demonstrated by the borylation of a range of structurally complex substrates. Remarkably, the reaction is catalyzed by phenothiazine, a simple organic photocatalyst with MW 200 that mediates the previously unachievable visible light-induced single electron reduction of phenol derivatives with reduction potentials as negative as approximately - 3 V versus SCE by a proton-coupled electron transfer mechanism. Mechanistic studies point to the crucial role of the photocatalyst-base interaction.

Para-selective borylation of monosubstituted benzenes using a transient mediator

Herein, we conceptualized a transient mediator approach that has the capability of para-selective C-H functionalization of monosubstituted aromatics. This approach is enabled by in situ generation of a versatile sulfonium salt via highly electrophilic phenoxathiine or thianthrene dication intermediate which can be readily generated from its sulfoxide with trifluoromethanesulfonic anhydride. Preliminary mechanistic study implied that the remarkable para selectivity might be related to the incredible electrophilicity of thianthrene dication intermediate. The versatility of this approach was demonstrated via para-borylation of various monosubstituted simple aromatics combining the sulfonium salt formation with further photocatalyzed transformation.

Pd-Catalyzed Site-Selective Borylation of Simple Arenes via Thianthrenation?

Site-selective borylation of simple arenes was realized in one pot via an electrophilic thianthrenation/Pd-catalyzed borylation sequence. The key to achieve this operatically simple process is the use of Pd catalysis, which could tolerate the solvent and acidic conditions used in the thianthrenation step. This protocol features mild conditions, broad functional group tolerance, and simple manipulations, and is suitable for late-stage functionalization of a wide range of pharmaceuticals and complex bioactive molecules.

Discovery, Optimization, and Target Identification of Novel Potent Broad-Spectrum Antiviral Inhibitors

Viral infections are increasing and probably long-lasting global risks. In this study, a chemical library was exploited by phenotypic screening to discover new antiviral inhibitors. After optimizations from hit to lead, a novel potent small molecule (RYL-634) was identified, showing excellent broad-spectrum inhibition activity against various pathogenic viruses, including hepatitis C virus, dengue virus, Zika virus, chikungunya virus, enterovirus 71, human immunodeficiency virus, respiratory syncytial virus, and others. The mechanism of action and potential targets of RYL-634 were further explored by the combination of activity-based protein profiling and other techniques. Finally, human dihydroorotate dehydrogenase was validated as the major target of RYL-634. We did not observe any mutant resistance under our pressure selections with RYL-634, and it had a strong synergistic effect with some Food and Drug Administration-approved drugs. Hence, there is great potential for developing new broad-spectrum antivirals based on RYL-634.

Exemplifying Prediction of Preferred Coupling Partners in Developing a Buchwald-Hartwig Coupling for the Synthesis of a c-Kit Inhibitor

Two convergent syntheses for compound 1 are described that apply Buchwald-Hartwig coupling as the key step. This development work provides a direct comparison of the coupling results from different coupling partners and illustrates that more efficiency ca

COMPOUNDS AND THEIR METHODS OF USE

The present invention is directed to, in part, fused heteroaryl compounds and compositions useful for preventing and/or treating a disease or condition relating to aberrant function of a voltage-gated, sodium ion channel, for example, abnormal late/persistent sodium current. Methods of treating a disease or condition relating to aberrant function of a sodium ion channel including Dravet syndrome or epilepsy are also provided herein.

SUBSTITUTED HETEROCYCLIC SULFONAMIDE COMPOUNDS USEFUL AS TRPA1 MODULATORS

The invention is concerned with the compounds of formula I or II: and salts thereof. In addition, the present invention relates to methods of manufacturing and methods of using the compounds of formula I or II as well as pharmaceutical compositions containing such compounds. The compounds may be useful in treating diseases and conditions mediated by TRPA1, such as pain.

Investigation of a lithium-halogen exchange flow process for the preparation of boronates by using a cryo-flow reactor

Conducting low-temperature organometallic reactions under continuous flow conditions offers the potential to more accurately control exotherms and thus provide more reproducible and scalable processes. Herein, progress towards this goal with regards to the lithium-halogen exchange/borylation reaction is reported. In addition to improving the scope of substrates available on a research scale, methods to improve reaction profiles and expedite purification of the products are also described. On moving to a continuous system, thermocouple measurements have been used to track exotherms and provide a level of safety for continuous processing of organometallic reagents. The use of an in-line continuous liquid-liquid separation device to circumvent labour intensive downstream off-line processing is also reported. A cool setup: A small footprint, modular setup based around a cryo-flow reactor is reported for the preparation of gram quantities of boronic esters. With minimum alteration, including the addition of a data logger with thermocouples and a liquid-liquid separator, the same equipment can be used to scale the process, inclusive of an in-line extraction. Copyright

SUBSTITUTED PYRIDOPYRAZINES AS NOVEL SYK INHIBITORS

Provided are pyridopyrazine compounds of formula (1), pharmaceutical compositions thereof and methods of use therefore, wherein R1, R2, R3, R4 and m are as defined in the specification.

METALLOENZYME INHIBITOR COMPOUNDS

The instant invention describes compounds having metalloenzyme modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by such metalloenzymes.