445303-67-3

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Fluoro-4-(trifluoromethyl)phenylboronic acid pinacol ester is used as a synthetic intermediate for the development of pharmaceuticals, leveraging its reactivity in cross-coupling reactions to construct complex molecular structures that can exhibit therapeutic effects.
Used in Agrochemical Development:
In the agrochemical industry, 3-Fluoro-4-(trifluoromethyl)phenylboronic acid pinacol ester is utilized as a key component in the synthesis of new agrochemicals, contributing to the creation of effective compounds for crop protection and enhancement of agricultural productivity.
Used in Material Science:
3-Fluoro-4-(trifluoromethyl)phenylboronic acid pinacol ester is employed as a building block in material science for the synthesis of novel materials with specific properties, such as high thermal stability or unique electronic characteristics, which can be applied in various high-tech industries.
Used in Organic Synthesis:
As a versatile reagent in organic synthesis, 3-Fluoro-4-(trifluoromethyl)phenylboronic acid pinacol ester is used for the formation of carbon-carbon bonds through cross-coupling reactions, facilitating the construction of diverse organic molecules with potential applications in various fields.

Upstream product

• 142808-15-9 4-bromo-2-fluoro-1-(trifluoromethyl)benzene 
• 73183-34-3 bis(pinacol)diborane 
• 392-85-8 1-fluoro-2-trifluoromethylbenzene 

Downstream Products

• 1255041-78-1 C₁₂H₁₀F₄O₂ 
• 1417332-63-8 methyl 4-amino-5-fluoro-6-(3-fluoro-4-(trifluoromethyl)-phenyl)picolinate 
• 1533422-43-3 C₁₃H₁₂F₇NO₄S 
• 1235407-46-1 5-fluoro-2-(pyridazin-4-yl)-4-(trifluoromethyl)phenol 
• 1235407-47-2 5-fluoro-2-iodo-4-(trifluoromethyl)phenol 
• 219581-07-4 3-fluoro-4-(trifluoromethyl)phenol 
• 1354819-06-9 5-chloro-2-fluoro-4-[5-fluoro-2-pyridazin-4-yl-4-(trifluoromethyl)phenoxy]-N-1,3-thiazol-4-ylbenzenesulfonamide 4-methylbenzenesulfonate 
• 1354818-79-3 5-chloro-2-fluoro-4-[5-fluoro-2-pyridazin-4-yl-4-(trifluoromethyl)phenoxy]-N-1,3-thiazol-4-ylbenzenesulfonamide 
• 1110771-95-3 ethyl 5-(3-fluoro-4-(trifluoromethyl)phenyl)-4-methylisoxazole-3-carboxylate 

Relevant academic research and scientific papers

Ligand-Enabled, Iridium-Catalyzed ortho-Borylation of Fluoroarenes

A terpyridine derivative and an iridium complex catalyze the C-H borylation of a stoichiometric amount of a fluoroarene with high ortho-selectivity and tolerance of functional groups such as bromide, chloride, ester, ketone, amine, and in situ-borylated hydroxyl. Complex drug molecules such as haloperidol can be selectively borylated ortho to the F atom. The terpyridine ligand undergoes rollover cyclometalation to produce an N,N,C-coordinated iridium complex, which may either selectively borylate the fluoroarene by itself or undergo reductive elimination to produce a borylated ligand.

Cobalt-Catalyzed Borylation of Fluorinated Arenes: Thermodynamic Control of C(sp2)-H Oxidative Addition Results in ortho-to-Fluorine Selectivity

The mechanism of C(sp2)-H borylation of fluorinated arenes with B2Pin2 (Pin = pinacolato) catalyzed by bis(phosphino)pyridine (iPrPNP) cobalt complexes was studied to understand the origins of the uniquely high ortho-to-fluorine regioselectivity observed in these reactions. Variable time normalization analysis (VTNA) of reaction time courses and deuterium kinetic isotope effect measurements established a kinetic regime wherein C(sp2)-H oxidative addition is fast and reversible. Monitoring the reaction by in situ NMR spectroscopy revealed the intermediacy of a cobalt(I)-aryl complex that was generated with the same high ortho-to-fluorine regioselectivity associated with the overall catalytic transformation. Deuterium labeling experiments and stoichiometric studies established C(sp2)-H oxidative addition of the fluorinated arene as the selectivity-determining step of the reaction. This step favors the formation of ortho-fluoroaryl cobalt intermediates due to the ortho fluorine effect, a phenomenon whereby ortho fluorine substituents stabilize transition metal-carbon bonds. Computational studies provided evidence that the cobalt-carbon bonds of the relevant intermediates in (iPrPNP)Co-catalyzed borylation are strengthened with increasing ortho fluorine substitution. The atypical kinetic regime involving fast and reversible C(sp2)-H oxidative addition in combination with the thermodynamic preference for forming cobalt-aryl bonds adjacent to fluorinated sites are the origin of the high regioselectivity in the catalytic borylation reaction.

Discovery and evaluation of 3,5-disubstituted indole derivatives as Pim kinase inhibitors

Pim kinases are promising therapeutic targets for the treatment of hematological cancers. A potent Pim kinase inhibitor 7f, derived from meridianin C, was further optimized by the replacement of 2-aminopyrimidine with substituted benzene. The optimization of the C-3 and C-5 positions of indole yielded compound 43 with improved cellular potency and high selectivity against a panel of 14 different kinases.

C(sp2)-H Borylation of Fluorinated Arenes Using an Air-Stable Cobalt Precatalyst: Electronically Enhanced Site Selectivity Enables Synthetic Opportunities

Cobalt catalysts with electronically enhanced site selectivity have been developed, as evidenced by the high ortho-to-fluorine selectivity observed in the C(sp2)-H borylation of fluorinated arenes. Both the air-sensitive cobalt(III) dihydride boryl 4-Me-(iPrPNP)Co(H)2BPin (1) and the air-stable cobalt(II) bis(pivalate) 4-Me-(iPrPNP)Co(O2CtBu)2 (2) compounds were effective and exhibited broad functional group tolerance across a wide range of fluoroarenes containing electronically diverse functional groups, regardless of the substitution pattern on the arene. The electronically enhanced ortho-to-fluorine selectivity observed with the cobalt catalysts was maintained in the presence of a benzylic dimethylamine and hydrosilanes, overriding the established directing-group effects observed with precious-metal catalysts. The synthetically useful selectivity observed with cobalt was applied to an efficient synthesis of the anti-inflammatory drug flurbiprofen.

Fluorine-controlled C-H borylation of arenes catalyzed by a PSiN-pincer platinum complex

An efficient, regioselective synthesis of fluorine-substituted arylboronic esters was achieved through fluorine-controlled C-H borylation of arenes with diboron catalyzed by a PSiN-platinum complex. The promising utility of the PSiN-platinum catalyst and its unique regioselectivity were demonstrated for the first time, which would complement the well-developed Ir-catalyzed C-H borylation.

SUBSTITUTED PIPERIDINES

The invention relates to novel substituted piperidines, to processes for preparation thereof, to the use thereof for treatment and/or prophylaxis of diseases and to the use thereof for production of medicaments for treatment and/or prophylaxis of diseases, especially of cardiovascular disorders and tumour disorders.

SUBSTITUTED PHENYLLUREAS AND PHENYLAMIDES AS VANILLOID RECEPTOR LIGANDS

The invention relates to substituted phenylureas and phenylamides of formula (I), to processes for the preparation thereof, to pharmaceutical compositions containing these compounds and also to the use of these compounds for preparing pharmaceutical compositions.

ISOXAZOL-3(2H)-ONE ANALOGS AS THERAPEUTIC AGENTS

or a pharmaceutically suitable salt thereof, wherein, R1 and R2 independently are hydrogen, deuterium, aryl, hetero aryl, C1-C8 alkyl, optionally being substituted with one or more substituents independently being R3,R3 is an aryl, hetero aryl, fluorine(s), a C1-C6 alkyl containing one or more fluorine, a C1-C6 alkyl containing one or more deuterium, a C1-C6 alkyl containing hydroxy, the aryl and heteroaryl optionally being substituted with one or more halogen, a fluorinated alkoxy, a fluorinated alkyl, a sulfonyl, one or more deuterium, a C1-6 alkyl, a C1-6 alkoxy, a nitrile,or R3 is a C1-6 alkyl optionally substituted with one or more of the following groups: COOR4, OCOR4, CONR5R6, NR5COR6, OR4;wherein, R4 is a C1-10 alkyl optionally substituted with one or more fluorine, deuterium, alkoxy, arylcarboxylate, alkyl carboxylate;R5 and R6 are independently selected from hydrogen, alkyl or they may together form a 4-8 membered carbon ring;or R1 and R2 form a 3-10 membered carbon ring optionally comprising O or N and optionally substituted with a C1-10 alkyl or aryl, hetero aryl optionally substituted with R3.

Compounds, compositions and methods

Compounds useful for treating cellular proliferative diseases and disorders by modulating the activity of KSP are disclosed.

COMPOUNDS, COMPOSITIONS AND METHODS

Compounds useful for treating cellular proliferative diseases and disorders by modulating the activity of KSP are disclosed.