380499-68-3

Usage

Uses

Used in Organic Synthesis:
4-Chlorocarbonylphenylboronic acid propanediol ester is used as a cross-coupling reagent for the formation of carbon-carbon and carbon-heteroatom bonds, facilitating the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Chlorocarbonylphenylboronic acid propanediol ester is used as a building block in the development of various drugs and biologically active molecules, contributing to the creation of novel therapeutic agents.
Used in Research and Development:
4-Chlorocarbonylphenylboronic acid propanediol ester is utilized by synthetic chemists as a research tool for exploring new synthetic pathways and developing innovative methods in organic chemistry, due to its mild and versatile reactivity.

Upstream product

• 180516-87-4 4-carboxyphenylboronic acid pinacol ester 
• 7719-09-7 thionyl chloride 
• 14047-29-1 4-carboxyphenylboronic acid 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 79-37-8 oxalyl dichloride 

Downstream Products

• 656239-37-1 4-(4,4,5,5-tetramethyl-[1,2,3]-dioxaborolan-2-yl)-N-(tetrahydropyran-4-yl)-benzamide 
• 879486-51-8 N-(1-methylpiperidin-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide 
• 1419221-30-9 N-(4-fluoropyridin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide 
• 1418307-28-4 (S)-benzyl 2-(8-methyl-1-(4-(4-propylpyridin-2-ylcarbamoyl)phenyl)imidazo[1 ,5-a]pyrazin-3-yl)piperidine-1-carboxylate 
• 1418307-29-5 (S)-4-(8-methyl-3-(piperidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(4-propylpyridin-2-yl)benzamide 
• 1008138-94-0 N-neopentyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide 

Relevant academic research and scientific papers

A synthetic route to 1-(4-boronobenzyl)-1H-pyrrole

The synthesis of 1-(4-boronobenzyl)-1H-pyrrole was investigated using three different routes. Two key routes that involved the introduction of the boronate group protected as the pinacol ester, failed, due to deprotection problems. The route involving the

Aminonorbornane derivative and preparation method and application thereof

The invention discloses an aminonorbornane derivative and a preparation method and application thereof and relates to a compound having a structure represented by a formula I which is described in thespecification or a pharmaceutically acceptable salt, a solvate, an active metabolite, a polymorph, an ester, an optical isomer or a prodrug thereof, a pharmaceutical composition comprising the compound as shown in the formula I, and application of the compound and the pharmaceutical composition as highly selective Bruton's tyrosine kinase (BTK) inhibitors of BTK (C481S) mutants for preparation ofdrugs used for prevention or treatment of heteroimmune diseases, autoimmune diseases or cancer.

Redox-Neutral ortho Functionalization of Aryl Boroxines via Palladium/Norbornene Cooperative Catalysis

Palladium/norbornene (Pd/NBE) cooperative catalysis, also known as the Catellani reaction, has become an increasingly useful method for site-selective arene functionalization; however, certain constraints still exist because of its intrinsic mechanistic pathway. Herein, we report a redox-neutral ortho functionalization of aryl boroxines via Pd/NBE catalysis. An electrophile, such as carboxylic acid anhydrides or O-benzoyl hydroxylamines, is coupled at the boroxine ortho position, and a proton as the second electrophile is introduced at the ipso position. This reaction does not require extra oxidants or reductants and avoids stoichiometric bases or acids, thereby tolerating a wide range of functional groups. In particular, orthogonal chemoselectivity between aryl iodide and boroxine moieties is demonstrated, which could be used to control reaction sequences. Finally, a deuterium-labeling study supports the ipso protonation pathway. This unique mechanistic feature could inspire the development of a new class of Pd/NBE-catalyzed transformations.Poly-substituted aromatics are ubiquitously found in drugs and agrochemicals. To realize streamlined synthesis, it is highly attractive if functional groups can be site-selectively introduced at unactivated positions with common arene starting materials. Here, a method is developed to directly introduce acyl and amino groups at unactivated ortho positions of readily available aryl boron compounds. Compared with the known ortho functionalization approaches, this method does not require stoichiometric bases, external oxidants, or reductants. Consequently, the reaction is chemoselective: a wide range of functional groups, including highly reactive aryl iodides, can be tolerated. The primary innovation lies in the use of a proton to terminate the ipso aryl intermediate and regenerate the active palladium catalyst. This unique mode of reactivity in the palladium/norbornene catalysis should open the door for developing new redox-neutral methods for site-selective arene functionalization.A redox-neutral ortho functionalization of aryl boroxines via palladium/norbornene cooperative catalysis is developed. The ortho amination and acylation are achieved with carboxylic acid anhydrides and O-benzoyl hydroxylamines as an electrophile, respectively, whereas protonation occurs at the ipso position. This transformation avoids using either extra oxidants and reductants or stoichiometric bases and acids. In addition, orthogonal chemoselectivity between aryl iodide and boroxine moieties is demonstrated for pathway divergence.

Cobalt-Catalyzed Aminocarbonylation of Alkyl Tosylates: Stereospecific Synthesis of Amides

Metal-catalyzed aminocarbonylation is a standard approach for installing amide functionality in chemical synthesis. Despite broad application of this transformation using aryl or vinyl electrophiles, there are few examples involving unactivated aliphatic substrates. Furthermore, there are no stereocontrolled aminocarbonylations of alkyl electrophiles known. Herein, we report a stereospecific aminocarbonylation of unactivated alkyl tosylates for the synthesis of enantioenriched amides. This cobalt-catalyzed transformation uses a remarkably broad range of amines and proceeds with excellent stereospecificity and chemoselectivity.

IMIDAZO [1,2-C] QUINAZOLIN-5-AMINE COMPOUNDS WITH A2A ANTAGONIST PROPERTIES

Disclosed are compounds having the structure of Formula I, or a pharmaceutically acceptable salt of any thereof: wherein: "Z" and R1 are defined herein, which compounds are believed suitable for use in selectively antagonizing the A2a receptors, for example, those found in high density in the basal ganglia. Such compounds and pharmaceutical formulations are believed to be useful in treatment or management of neurodegenerative diseases, for example, Parkinson's disease, or movement disorders arising from use of certain medications used in the treatment or management of Parkinson's disease.

Imidazopyrazines as Selective BTK Inhibitors

The invention relates to imidazopyrazine compounds as selective Bruton's tyrosine kinase (BTK) inhibitors. In particular, the invention discloses (S)-4-(8-amino-3-(1-(butyl-2-acetylenyl) pyrrolidine-2-yl) imidazo [1, 5-a] pyrazine-1-yl)-N-(pyridine-2-yl) benzamide and a deuterated compound of an optical isomer thereof, or a pharmaceutically acceptable salt or to a pharmaceutical composition containing the compound, and use thereof in the treatment of BTK-mediated diseases.

CERTAIN CHEMICAL ENTITIES, COMPOSITIONS, AND METHODS

Chemical entities that are kinase inhibitors, pharmaceutical compositions and methods of treatment of cancer are described.

BRUTON'S TYROSINE KINASE INHIBITORS

Bruton's tyrosine kinase (Btk) inhibitors have the following Formula (I).

Palladium- and Nickel-Catalyzed Decarbonylative C-S Coupling to Convert Thioesters to Thioethers

This Letter describes the development of a catalytic decarbonylative C-S coupling reaction that transforms thioesters into thioethers. Both Pd- and Ni-based catalysts are developed and applied to the construction of diaryl, aryl alkyl, and heterocycle-containing thioethers.

Irreversible Cysteine-Selective Protein Labeling Employing Modular Electrophilic Tetrafluoroethylation Reagents

Fluoroalkylation reagents based on hypervalent iodine are widely used to transfer fluoroalkyl moieties to various nucleophiles. However, the transferred groups have so far been limited to simple structural motifs. We herein report a reagent featuring a secondary amine that can be converted to amide, sulfonamide, and tertiary amine derivatives in one step. The resulting reagents bear manifold functional groups, many of which would not be compatible with the original synthetic pathway. Exploiting this structural versatility and the known high reactivity toward thiols, the new-generation reagents were used in bioconjugation with an artificial retro-aldolase, containing an exposed cysteine and a reactive catalytic lysine. Whereas commercial reagents based on maleimide and iodoacetamide labeled both sites, the iodanes exclusively modified the cysteine residue. The study thus demonstrates that modular fluoroalkylation reagents can be used as tools for cysteine-selective bioconjugation.