797762-23-3

Usage

Uses

Used in Organic Synthesis:
3-Methoxybenzylboronic acid pinacol ester is used as a reagent for the introduction of the 3-methoxybenzyl group into various organic molecules. Its ability to form stable intermediates and facilitate coupling reactions makes it a valuable component in the synthesis of complex organic compounds.
Used in Pharmaceutical Preparation:
In the pharmaceutical industry, 3-Methoxybenzylboronic acid pinacol ester is utilized for the preparation of various drugs. Its unique chemical properties allow for the creation of new molecular structures with potential therapeutic effects, contributing to the development of novel medications.
Used in Agrochemical Production:
3-Methoxybenzylboronic acid pinacol ester is also employed in the production of agrochemicals. Its reactivity and functional group make it suitable for the synthesis of active ingredients in pesticides, herbicides, and other agricultural chemicals, enhancing crop protection and yield.
Used in Fine Chemicals Synthesis:
3-Methoxybenzylboronic acid pinacol ester is used in the synthesis of fine chemicals, which are high-purity chemicals used in various industries, including fragrances, dyes, and specialty chemicals. The versatility of 3-Methoxybenzylboronic acid pinacol ester allows for the creation of a wide range of fine chemicals with specific properties and applications.
Used in Medicinal Chemistry Research:
3-Methoxybenzylboronic acid pinacol ester has been studied for its potential applications in medicinal chemistry due to its unique reactivity and properties. Researchers are exploring its use in the development of new drugs and therapeutic agents, leveraging its ability to form stable intermediates and participate in various chemical reactions.
Used in Materials Chemistry Research:
In the field of materials chemistry, 3-Methoxybenzylboronic acid pinacol ester is being investigated for its potential use in the development of new materials with specific properties. Its reactivity and functional group may contribute to the creation of advanced materials for various applications, such as sensors, catalysts, and coatings.

Upstream product

• 19350-71-1 N'-(3-methoxybenzylidene)-4-methylbenzenesulfonohydrazide 
• 73183-34-3 bis(pinacol)diborane 
• 591-31-1 3-methoxy-benzaldehyde 
• 153974-48-2 3-methoxy-O-tert-butyldimethylsilylbenzyl alcohol 
• 824-98-6 m-methoxybenzyl chloride 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 10365-98-7 3-methoxyphenylboronic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 6971-51-3 3-methoxybenzyl alcohol 
• 100-84-5 1-methoxy-3-methyl-benzene 
• 66107-33-3 3-methoxyphenyl triflate 
• 78782-17-9 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 745783-97-5 triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 

Downstream Products

• 1604802-28-9 2-((4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-5-(3-methoxybenzyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one 
• 1604800-76-1 2-((4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)pyrrolo[2,1-f][1,2,4]triazin-4(3H)-one 

Relevant academic research and scientific papers

Nickel-Catalyzed Ipso-Borylation of Silyloxyarenes via C-O Bond Activation

The conversion of silyloxyarenes to boronic acid pinacol esters via nickel catalysis is described. In contrast to other borylation protocols of inert C-O bonds, the method is competent in activating the carbon-oxygen bond of silyloxyarenes in isolated aromatic systems lacking a directing group. The catalytic functionalization of benzyl silyl ethers was also achieved under these conditions. Sequential cross-coupling reactions were achieved by leveraging the orthogonal reactivity of silyloxyarenes, which could then be functionalized subsequently.

Extremely facile formation of the pavine alkaloid skeleton by the photoreaction between isoquinoline and benzyltrifluoroborate

Appling the photo-benzylation of isoquinoline with benzyltrifluoroborate, an extremely facile method for the construction of a pavine alkaloid skeleton was developed. When 3-methoxybenzylboron reagents were employed to the reaction, it was found that not

Method for synthesizing alkylborate compound

The invention discloses a method for synthesizing an alkylborate compound, and concretely relates to a method for synthesizing the alkylborate compound through a cross-coupling reaction of chloralkaneand bis(pinacolato)diboron in the presence of metallic magnesium with Fe(acac)3 (acac = an acetylacetonate group) as a single component catalyst. The method for synthesizing the alkylborate compoundavoids the use of sensitive metal organic solvents and multi-component catalysts, realizes bilateral utilization of the bis(pinacolato)diboron, greatly reduces the use amount of the bis(pinacolato)diboron, and allows the coupling reaction of the cheap and easily-available chloralkane to be smoothly carried out under mild conditions; and compared with methods reported in literatures, the method disclosed in the invention has a better atom economy, a same or higher catalysis efficiency and a wider substrate applicability.

Benzyltriboronates: Building Blocks for Diastereoselective Carbon-Carbon Bond Formation

A highly diastereoselective carbon-carbon bond-forming reaction involving the tandem coupling of benzyltriboronates, enoates, and alkyl halides is described. This method was enabled by the discovery of α-diimine nickel catalysts that promote the chemosele

Synthesis of Benzyl-, Allyl-, and Allenyl-boronates via Copper-Catalyzed Borylation of Alcohols

Alcohols are among the most abundant and readily available organic feedstocks in industrial processes. The direct catalytic functionalization of sp3 C-O bonds of alcohols remains the main challenge in this field. Here, we report a copper-cataly

Preparation method of benzyl boron ester compound

The invention discloses a preparation method of a benzyl boron ester compound. According to the preparation method, aromatic boric acid Ar-B(OH)2, trimethyl silicon-based diazomethane, pinacol and tetrabutyl ammonium fluoride are subjected to a reaction in an organic solvent so as to obtain a benzyl pinacol boron ester compound, wherein Ar represents a non-heterocyclic aromatic group. After the method is adopted, the benzyl boron ester compound is obtained by starting from the aromatic boric acid and converting under a one-pot condition; the method is mild in reaction conditions, the reaction related to the method occurs smoothly in the air without needing strict water-free and oxygen-free conditions, and the method is convenient and simple to operate; the method has better tolerance and universality for functional groups and does not need an expensive metal catalyst and a ligand, thus being lower in reaction cost and being widely used for preparing the benzyl boron ester compound.

Pd-catalyzed cross-coupling of 1,1-diborylalkanes with aryl triflates

The Pd-catalyzed synthesis of benzylboronic esters through coupling of aryl triflates with 1,1-diborylalkane under ambient conditions is described. Varieties of primary and secondary arylboronic esters could be successfully synthesized by this strategy. C

METHODS FOR PRODUCING BORYLATED ARENES

Methods for the borylation of aromatic compounds using cobalt catalysts are provided.

Iridium-Catalyzed Borylation of Primary Benzylic C-H Bonds without a Directing Group: Scope, Mechanism, and Origins of Selectivity

Primary benzylic boronate esters are useful intermediates in organic synthesis, but these reagents cannot be prepared by hydroboration. The benzylic C-H borylation of methylarenes would be a method to form these products, but such reactions without neat methylarene or a directing group are unknown. We report an approach to divert the borylation of methylarenes from aromatic positions to benzylic positions with a silylborane as reagent and a new iridium catalyst containing an electron-deficient phenanthroline as ligand. This system forms benzylic boronate esters selectively over the corresponding aryl boronate esters. An Ir diboryl monosilyl complex ligated by the phenanthroline was isolated and determined to be the resting state of the catalyst. Mechanistic studies show that this complex is kinetically competent to be an intermediate in the catalytic process. Kinetic studies of benzylic and aryl C-H borylation catalyzed by various Ir complexes show that the rate of aryl C-H borylation decreases with decreasing electron density at the metal center of the Ir catalyst, but that the rate of benzylic C-H borylation is less sensitive to the degree of electron density at the metal center of the Ir catalyst. Kinetic and computational studies suggest that the two borylation reactions respond differently to the degree of electron density at the metal center because they occur with different turnover-limiting steps. The turnover-limiting step in the borylation of aryl C-H bonds is known to be C-H oxidative addition, but the turnover-limiting step of the borylation of benzylic C-H bonds appears to be an isomerization prior to C-B reductive elimination.

PYRROLOTRIAZINONE DERIVATIVES AS PI3K INHIBITORS

New pyrrolotriazinone derivatives having the chemical structure of formula (I) are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of Phosphoinositide 3-Kinases (PI3Ks).