406463-06-7

Usage

Uses

Used in Organic Synthesis:
6-Quinolineboronic acid pinacol ester, 97% is used as a reagent in organic synthesis for the construction of complex organic molecules. Its ability to participate in Suzuki-Miyaura cross-coupling reactions allows for the efficient formation of carbon-carbon bonds, facilitating the synthesis of a wide range of organic compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 6-Quinolineboronic acid pinacol ester, 97% is utilized as a building block for the development of pharmaceutical compounds. Its unique structure and reactivity enable the synthesis of novel drug candidates with potential therapeutic applications.
Used in Research Applications:
6-Quinolineboronic acid pinacol ester, 97% is employed as a research chemical in academic and industrial laboratories. Its high purity of 97% ensures that it is suitable and reliable for use in various research projects, including the investigation of new synthetic methods, the development of new compounds, and the study of reaction mechanisms.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 6-Quinolineboronic acid pinacol ester, 97% is used as an intermediate in the synthesis of active pharmaceutical ingredients (APIs). Its versatility in chemical reactions allows for the efficient production of APIs with desired properties, contributing to the development of new drugs and therapies.
Used in Chemical Synthesis Industry:
6-Quinolineboronic acid pinacol ester, 97% is utilized in the chemical synthesis industry as a key intermediate for the production of various specialty chemicals. Its high purity and reactivity make it an essential component in the synthesis of compounds used in various applications, such as agrochemicals, dyes, and materials science.

InChI:InChI=1/C15H18BNO2/c1-14(2)15(3,4)19-16(18-14)12-7-8-13-11(10-12)6-5-9-17-13/h5-10H,1-4H3

Upstream product

• 5332-25-2 6-bromoquinoline 
• 73183-34-3 bis(pinacol)diborane 
• 13327-31-6 6-iodoquinoline 
• 10349-57-2 Quinoline-6-carboxylic acid 
• 135808-70-7 1-(quinolin-6-yl)butan-1-one 
• 106-40-1 4-bromo-aniline 
• 426265-40-9 quinolin-6-yl 4-methylbenzene-1-sulfonate 
• 580-16-5 6-hydroxyquinoline 
• 1092513-18-2 quinolin-6-yl methanesulfonate 
• 612-57-7 6-chloroquinoline 

Downstream Products

• 1021915-68-3 1-(1-phenylethyl)-6-(quinolin-6-yl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one 
• 1056882-02-0 3-quinolin-6-yl-cyclohex-2-enone 
• 1148008-66-5 N-[2-(ethyloxy)-5-(6-quinolinyl)-3-pyridinyl]benzenesulfonamide 
• 1201842-65-0 N-(2-chloro-5-(6-quinolinyl)-3-pyridinyl)-4-methoxybenzenesulfonamide 
• 1246888-99-2 1-(2-(quinolin-6-yl)phenyl)ethanone 
• 1366767-57-8 6-[4-(4-{[1-(cyclopropylcarbonyl)-3-azetidinyl]methyl}-4H-1,2,4-triazol-3-yl)-3-fluorophenyl] quinoline 
• 1337933-01-3 C₂₆H₂₂N₂O₃S 
• 376581-24-7 6-quinolineboronic acid 
• 1454654-31-9 (4-morpholin-4-yl-phenyl)-(5-quinolin-6-yl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-amine 

Relevant academic research and scientific papers

Photocatalytic Cross-Couplings of Aryl Halides Enabled by o-Phosphinophenolate and o-Phosphinothiophenolate

o-Phosphinophenolate and o-phosphinothiophenolate are potent photocatalysts with strong reducing ability to activate aryl chlorides and bromides under visible light for borylation, arylation, and phosphorylation. Experimental and theoretical studies revealed that the o-diphenylphosphino substituent results in a narrow optical gap and facilitates intersystem crossing to access triplet states, which promote phenolate and thiophenolate to function as effective visible-light-photoredox catalysts. The results presented herein suggest promising utility of synthetically modified phenolates and thiophenolates as photoredox catalysts.

Transformations of Aryl Ketones via Ligand-Promoted C?C Bond Activation

The coupling of aromatic electrophiles (aryl halides, aryl ethers, aryl acids, aryl nitriles etc.) with nucleophiles is a core methodology for the synthesis of aryl compounds. Transformations of aryl ketones in an analogous manner via carbon–carbon bond activation could greatly expand the toolbox for the synthesis of aryl compounds due to the abundance of aryl ketones. An exploratory study of this approach is typically based on carbon–carbon cleavage triggered by ring-strain release and chelation assistance, and the products are also limited to a specific structural motif. Here we report a ligand-promoted β-carbon elimination strategy to activate the carbon–carbon bonds, which results in a range of transformations of aryl ketones, leading to useful aryl borates, and also to biaryls, aryl nitriles, and aryl alkenes. The use of a pyridine-oxazoline ligand is crucial for this catalytic transformation. A gram-scale borylation reaction of an aryl ketone via a simple one-pot operation is reported. The potential utility of this strategy is also demonstrated by the late-stage diversification of drug molecules probenecid, adapalene, and desoxyestrone, the fragrance tonalid as well as the natural product apocynin.

TRIAZOLO-PYRIMIDINE COMPOUNDS AND USES THEREOF

The present disclosure relates to novel triazolo-pyrimidine compounds targeting adenosine receptors (especially A1 and A2, particularly A2a). The present disclosure also relates to pharmaceutical compositions comprising one or more of the compounds as an active ingredient, and use of the compounds in the treatment of adenosine receptor (AR) associated diseases, for example cancer such as NSCLC, RCC, prostate cancer, and breast cancer.

Redox-Neutral Decarbonylative Cross-Couplings Coming of Age

Major progress has recently been made in the challenging redox-neutral decarbonylative cross-coupling of carboxylic acids. For example, the use of acid fluorides as effective cross-coupling partners has been found to enable control of the decarbonylation selectivity and facilitates challenging Pd0-catalyzed nucleophilic trifluoromethylation and exogenous base-free Suzuki cross-coupling reactions. In another recent advance, the use of acid chlorides in room temperature difluoromethylation and direct decarbonylative cross-coupling of carboxylic acids allows these classical substrates to be used as aryl electrophiles in cross-coupling reactions. Further challenges that are yet to be addressed in redox-neutral decarbonylative cross-couplings are also briefly summarized.

1,2,4-TRIAZINE-3-AMINE DERIVATIVE, PREPARATION METHOD THEREFOR, AND USE THEREOF IN MEDICINE

The present invention relates to a 1,2,4-triazine-3-amine derivative, a preparation therefor, and use thereof in medicine. Specifically, the present invention relates to a 1,2,4-triazine-3-amine derivative as represented by general formula (I), a preparation method therefor, a pharmaceutical composition comprising the derivative, and use thereof as a therapeutic agent, in particular as an A2a receptor antagonist, and use thereof in the preparation of a medicament for treating a condition or disorder that is ameliorated by means of inhibition of the A2a receptor, each substituent in general formula (I) being same as defined in the description.

Copper-catalysed borylation of aryl chlorides

We report herein the first Cu-catalysed borylation of a wide range of aryl chlorides with different electronic and steric properties using a readily prepared NHC-stabilised Cu catalyst and KOtBu as the base with B2pin2 (pin = pinacolato) as the boron reagent. The aryl chlorides are converted into their corresponding arylboronic esters in good yields. The new procedure shows broad functional group tolerance, and B2neop2 (neop = neopentyl glycolato) can also be applied as the boron reagent.

Visible-Light-Induced Organocatalytic Borylation of Aryl Chlorides

The preparation of arylboronates from unactivated aryl chlorides in a transition-metal-free manner is rather challenging. There are only few examples to achieve this goal by using ultraviolet irradiation. Based on the mechanistic understanding of the diboron/methoxide/pyridine reaction system, we achieved photoactivation of the in situ generated super electron donor and developed a visible-light-induced organocatalytic method for efficient borylation of unactivated aryl chlorides.

Palladium-Catalyzed Decarbonylative Borylation of Carboxylic Acids: Tuning Reaction Selectivity by Computation

Decarbonylative borylation of carboxylic acids is reported. Carbon electrophiles are generated directly after reagent-enabled decarbonylation of the in situ accessible sterically-hindered acyl derivative of a carboxylic acid under catalyst controlled conditions. The scope and the potential impact of this method are demonstrated in the selective borylation of a variety of aromatics (>50 examples). This strategy was used in the late-stage derivatization of pharmaceuticals and natural products. Computations reveal the mechanistic details of the unprecedented C?O bond activation of carboxylic acids. By circumventing the challenging decarboxylation, this strategy provides a general synthetic platform to access arylpalladium species for a wide array of bond formations from abundant carboxylic acids. The study shows a powerful combination of experiment and computation to predict decarbonylation selectivity.

Preparation method of benzoheterocyclic boric acid

The invention provides a preparation method of benzoheterocyclic boric acid. The preparation method comprises steps as follows: (1) a benzoheterocyclic compound shown in a formula I is dissolved in asolvent A, a liquor A is obtained, a boronylation reagent is dissolved in a solvent B, a liquor B is obtained, a palladium catalyst and an alkaline reagent are immobilized on a channel of a continuousflow reactor, the liquor A and the liquor B are subjected to a continuous adding reaction, the reaction is stopped after the mixture flows out of a reaction tube, and an intermediate is obtained; (2)the intermediate obtained in step (1) is subjected to a hydrolysis reaction, and benzoheterocyclic boric acid is obtained. According to the provided preparation method, the benzoheterocyclic boric acid is synthesized with a flow chemical technology. Compared with methods in the prior art, the method has the advantages that the product yield is 86% or above, the highest yield can reach 90% or above, the yield is very high, the reaction rate is high, energy consumption of a reaction is reduced greatly, and the method is high in operability, high in automation degree and favorable for productionoperation and industrial production.

Isonicotinate Ester Catalyzed Decarboxylative Borylation of (Hetero)Aryl and Alkenyl Carboxylic Acids through N-Hydroxyphthalimide Esters

Decarboxylative borylation of aryl and alkenyl carboxylic acids with bis(pinacolato)diboron was achieved through N-hydroxyphthalimide esters using tert-butyl isonicotinate as a catalyst under base-free conditions. A variety of aryl carboxylic acids possessing different functional groups and electronic properties can be smoothly converted to aryl boronate esters, including those that are difficult to decarboxylate under transition-metal catalysis, offering a new method enabling use of carboxylic acid as building blocks in organic synthesis. Mechanistic analysis suggests the reaction proceeds through coupling of a transient aryl radical generated by radical decarboxylation with a pyridine-stabilized persistent boryl radical. Activation of redox active esters may proceed via an intramolecular single-electron-transfer (SET) process through a pyridine-diboron-phthalimide adduct and accounts for the base-free reaction conditions.