480425-35-2

Usage

Uses

Used in Pharmaceutical Industry:
3-Methoxycarbonylphenylboronic acid pinacol ester is used as a key intermediate in the synthesis of non-novosyl-coupled coumermycin A1 analogs. These analogs are specifically designed to target heat shock protein 90 (Hsp90) dimer, which plays a crucial role in various cellular processes and is often overexpressed in cancer cells. By inhibiting the dimerization of Hsp90, these analogs can potentially disrupt the stability and function of the protein, leading to the suppression of tumor growth and progression.
Additionally, 3-Methoxycarbonylphenylboronic acid pinacol ester may also be utilized in the development of other pharmaceutical compounds due to its unique chemical structure and reactivity, further expanding its applications in the pharmaceutical industry.

InChI:InChI=1/C14H19BO4/c1-13(2)14(3,4)19-15(18-13)11-8-6-7-10(9-11)12(16)17-5/h6-9H,1-5H3

Upstream product

• 6018-41-3 methyl coumalate 
• 347389-74-6 2-ethynyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 59776-81-7 methyl 2-pyrone-4-carboxylate 
• 25991-27-9 methyl 2-oxo-2H-pyrane-3-carboxylate 
• 93-58-3 benzoic acid methyl ester 
• 73183-34-3 bis(pinacol)diborane 
• 19438-10-9 methyl 3-hydroxybenzoate 
• 161912-35-2 methyl 3-((methylsulfonyl)oxy)benzoate 
• 107658-28-6 methyl 3-(trifluoromethylsulfonyloxy)benzoate 
• 1276637-19-4 C₆H₅SO₂O(C₆H₄COOCH₃) 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 2905-65-9 methyl 3-chlorobenzoate 
• 618-89-3 methyl 3-bromobenzoate 
• 76-09-5 2,3-dimethyl-2,3-butane diol 

Downstream Products

• 1229227-11-5 C₁₇H₁₇NO₃ 
• 1751-97-9 biphenyl-3,3'-dicarboxylic acid dimethyl ester 
• 269409-73-6 3-carboxyphenylboronic acid pinacol ester 
• 455-68-5 methyl 3-fluorobenzoate 
• 1431773-69-1 methyl 3-(6-aminopyridazin-3-yl)benzoate 
• 19438-10-9 methyl 3-hydroxybenzoate 
• 2557-13-3 3-trifluoromethylbenzoic acid methyl ester 
• 1573998-32-9 methyl 3-(3-(((tert-butoxycarbonyl)((R)-1-(naphthalen-1-yl)ethyl)amino)methyl)-3,4-dihydronaphthalen-1-yl)benzoate 
• 1573998-30-7 methyl 3-(3-((((R)-1-(naphthalen-1-yl)ethyl)amino)methyl)-1,2,3,4-tetrahydronaphthalen-1-yl)benzoate 
• 1573998-36-3 methyl 3-(3-(((tert-butoxycarbonyl)((R)-1-(naphthalen-1-yl)ethyl)amino)methyl)-1,2,3,4-tetrahydronaphthalen-1-yl)benzoate 
• 1431773-94-2 methyl 3-(8-(6-(3,5-dimethylpiperidin-1yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoate hydrochloride 
• 1431772-72-3 (R)-3-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acid hydrochloride 
• 1431772-99-4 (S)-3-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acid 
• 1431772-92-7 (3-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)phenyl)(morpholino)methanone 

Relevant academic research and scientific papers

IrIII-based Octahedral Metalloligands Derived Primitive Cubic Frameworks for Enhanced CO2/N2 Separation

We developed a metalloligand strategy to construct porous frameworks, viz. the combined use of IrIII-based octahedral metalloligands and the linear unit [Ni(cyclam)] easily afforded two isostructural complexes 1 and 2 with primitive cubic frameworks. Both complexes show good CO2/N2 separation property.

Cross-Coupling through Ag(I)/Ag(III) Redox Manifold

In ample variety of transformations, the presence of silver as an additive or co-catalyst is believed to be innocuous for the efficiency of the operating metal catalyst. Even though Ag additives are required often as coupling partners, oxidants or halide scavengers, its role as a catalytically competent species is widely neglected in cross-coupling reactions. Most likely, this is due to the erroneously assumed incapacity of Ag to undergo 2e? redox steps. Definite proof is herein provided for the required elementary steps to accomplish the oxidative trifluoromethylation of arenes through AgI/AgIII redox catalysis (i. e. CEL coupling), namely: i) easy AgI/AgIII 2e? oxidation mediated by air; ii) bpy/phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) ulterior reductive elimination of benzotrifluorides from an [aryl-AgIII-CF3] fragment. More precisely, an ultimate entry and full characterization of organosilver(III) compounds [K]+[AgIII(CF3)4]? (K-1), [(bpy)AgIII(CF3)3] (2) and [(phen)AgIII(CF3)3] (3), is described. The utility of 3 in cross-coupling has been showcased unambiguously, and a large variety of arylboron compounds was trifluoromethylated via [AgIII(aryl)(CF3)3]? intermediates. This work breaks with old stereotypes and misconceptions regarding the inability of Ag to undergo cross-coupling by itself.

Synthesis and evaluation of tiaprofenic acid-derived UCHL5 deubiquitinase inhibitors

The ubiquitin–proteasome system (UPS) plays an important role in maintaining protein homeostasis by degrading intracellular proteins. In the proteasome, poly-ubiquitinated proteins are deubiquitinated by three deubiquitinases (DUBs) associated with 19S re

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.

Reductive Electrophotocatalysis: Merging Electricity and Light to Achieve Extreme Reduction Potentials

We describe a new electrophotocatalytic strategy that harnesses the power of light and electricity to generate an excited radical anion with a reducing potential of -3.2 V vs SCE, which can be used to activate substrates with very high reduction potentials (Ered ≈ -1.9 to -2.9 V). The resultant aryl radicals can be engaged in various synthetically useful transformations to furnish arylboronate, arylstannane, and biaryl products.

Controllable factors of supported IR complex catalysis for aromatic C?H borylation

We have developed a catalyst in which an Ir complex and organic functionalities are coimmobilized on the silica surface. The catalytic activity for aromatic C?H borylation was significantly affected by (i) the linker length of the Ir?bipyridine complex, (ii) the coimmobilized organic functionality, and (iii) the substituents on the aromatic substrate compounds. The fine-tuned supported catalyst showed higher activity than the homogeneous Ir?bipyridine complex when using a specific substrate such as benzonitrile. We elucidated this property by conducting solid-state NMR, FT-IR, XAFS, and in situ FT-IR analysis.

Hydride Transfer Enables the Nickel-Catalyzed ipso-Borylation and Silylation of Aldehydes

Nickel-catalyzed ipso-borylations and silylations of aldehydes are described for the first time. The new functional-group interconversion protocol is characterized by its scalability, functional-group tolerance and wide substrate scope, including examples of late-stage functionalization of complex molecules. The key for the successful reaction outcome is the use of a ketone as a hydride acceptor that intercepts the nickel hydride to undergo a reductive pathway, thus allowing formation of the desired C?B and C?Si bonds.

Cleavage of C(aryl)?CH3 Bonds in the Absence of Directing Groups under Transition Metal Free Conditions

Organic chemists now can construct carbon–carbon σ-bonds selectively and sequentially, whereas methods for the selective cleavage of carbon–carbon σ-bonds, especially for unreactive hydrocarbons, remain limited. Activation by ring strain, directing groups, or in the presence of a carbonyl or a cyano group is usually required. In this work, by using a sequential strategy site-selective cleavage and borylation of C(aryl)?CH3 bonds has been developed under directing group free and transition metal free conditions. Methyl groups of various arenes are selectively cleaved and replaced by boryl groups. Mechanistic analysis suggests that it proceeds by a sequential intermolecular oxidation and coupling of a transient aryl radical, generated by radical decarboxylation, involving a pyridine-stabilized persistent boryl radical.

Hydrogenation of (Hetero)aryl Boronate Esters with a Cyclic (Alkyl)(amino)carbene–Rhodium Complex: Direct Access to cis-Substituted Borylated Cycloalkanes and Saturated Heterocycles

We herein report the hydrogenation of substituted aryl- and heteroaryl boronate esters for the selective synthesis of cis-substituted borylated cycloalkanes and saturated heterocycles. A cyclic (alkyl)(amino)carbene-ligated rhodium complex with two dimethyl groups at the ortho-alkyl scaffold of the carbene showed high reactivity in promoting the hydrogenation, thereby enabling the hydrogenation of (hetero)arenes with retention of the synthetically valuable boronate group. This process constitutes a clean, atom-economic, as well as chemo- and stereoselective route for the generation of cis-configured, diversely substituted borylated cycloalkanes and saturated heterocycles that are usually elusive and difficult to prepare.

Hydrogen Bond Directed ortho-Selective C?H Borylation of Secondary Aromatic Amides

Reported is an iridium catalyst for ortho-selective C?H borylation of challenging secondary aromatic amide substrates, and the regioselectivity is controlled by hydrogen-bond interactions. The BAIPy-Ir catalyst forms three hydrogen bonds with the substrate during the crucial activation step, and allows ortho-C?H borylation with high selectivity. The catalyst displays unprecedented ortho selectivities for a wide variety of substrates that differ in electronic and steric properties, and the catalyst tolerates various functional groups. The regioselective C?H borylation catalyst is readily accessible and converts substrates on gram scale with high selectivity and conversion.