642494-37-9

Usage

Uses

Indole-7-boronic acid, pinacol ester

InChI:InChI=1/C14H18BNO2/c1-13(2)14(3,4)18-15(17-13)11-7-5-6-10-8-9-16-12(10)11/h5-9,16H,1-4H3

Upstream product

• 51417-51-7 7-bromo-1H-indole 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 2376879-92-2 2,2-dimethyl-1-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-1-yl)propan-1-one 
• 70957-04-9 N-pivaloyl indole 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 10294-33-4 boron tribromide 
• 120-72-9 indole 
• 919119-72-5 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-indole 
• 116491-57-7 2-trimethylsilanyl-1H-indole 
• 919119-70-3 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-trimethylsilanylindole 

Downstream Products

• 1169856-70-5 3-cyclohexyl-1H,1'H-[2,7']biindolyl-6-carboxylic acid methyl ester 
• 1169856-74-9 3-cyclohexyl-1-(2-methoxymethoxyethyl)-1H,1'H-[2,7']biindolyl-6-carboxylic acid methyl ester 
• 1863-21-4 7-(phenyl)-1H-indole 
• 1219637-86-1 7-cinnamylindole 
• 53924-05-3 7-chloro-1H-indole 
• 51417-51-7 7-bromo-1H-indole 
• 2380-84-9 7-Indolol 
• 52886-06-3 hippadine 
• 1426095-45-5 N-{[(3R)-1-cyclopropylcarbonyl-3-pyrrolidinyl]methyl}-4-(1H-indol-7-yl)-N-(phenylmethyl)benzamide 
• 1426095-06-8 N-{[(3S)-1-cyclopropylcarbonyl-3-pyrrolidinyl]methyl}-4-(1H-indol-7-yl)-N-methylbenzamide 
• 1426095-33-1 N-{[(3R)-1-cyclopropylcarbonyl-3-pyrrolidinyl]methyl}-4-(1H-indol-7-yl)-N-(1-methylethyl)benzamide 

Relevant academic research and scientific papers

Suzuki–Miyaura Cross-Coupling Reactions of Tetrahydroxanthones and 4-Chromanone Lactones to Heteromeric Biaryls

We are reporting on a Suzuki–Miyaura cross-coupling study of a tetrahydroxanthone model system with different boronic acids, pinacolboranes, and halides to afford heteromeric biaryls. We transferred these reaction conditions to the Suzuki–Miyaura cross-coupling reactions of 4-chromanone lactones. We thereby obtained complex building blocks offering a convenient starting point for further transformations towards various natural products with the tetrahydroxanthone structural motif. (Figure presented.).

Visible-light-mediated borylation of aryl and alkyl halides with a palladium complex

Palladium catalyzed visible-light-mediated borylation of inactivated aryl and alkyl halides is reported; the method provided high yields and excellent functional group compatibility. Furthermore, arylsilicates were synthesized selectively using dimethylphenylsilyl boronic ester via changing the reaction conditions. Finally, the possible reaction mechanism is determined through fluorescence quenching and turn on/off experiments.

Preparation method of indole type or aniline type borate

The invention discloses a preparation method of indole type or aniline type borate, which comprises the following step: reacting an indole type raw material or aniline type raw material with boron trihalide in an organic solvent under the protection of in

Metal-free directed sp 2-C–H borylation

Organoboron reagents are important synthetic intermediates that have a key role in the construction of natural products, pharmaceuticals and organic materials1. The discovery of simpler, milder and more efficient approaches to organoborons can

Acyl-Directed ortho-Borylation of Anilines and C7 Borylation of Indoles using just BBr3

Indoles are privileged heterocycles found in many biologically active pharmaceuticals and natural products. However, the selective functionalization of the benzenoid moiety in indoles in preference to the more reactive pyrrolic unit is a significant challenge. Herein we report that N-acyl directing groups enable the C7-selective C?H borylation of indoles using just BBr3. This transformation shows some functional-group tolerance and notably proceeds with C6 substituted indoles. The directing group can be readily removed in situ and the products isolated as the pinacol boronate esters. Acyl-directed electrophilic borylation can be extended to carbazoles and anilines with excellent ortho selectivity. 4-amino-indoles are amenable to this process, with acyl group installation and directed electrophilic C?H borylation enabling selective formation of C5-BPin-indoles.

2-ARYLAMINO PYRIDINE, PYRIDINE OR TRIAZINE DERIVATIVE, PREPARATION METHOD AND USE THEREOF

The present disclosure relates to 2-arylamino pyridine, pyrimidine, or triazine derivatives, and the preparation method and use thereof. The 2-arylamino pyridine, pyrimidine, or triazine derivatives may act on certain mutated forms of epidermal growth fac

ORGANIC LIGHT-EMITTING COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME

The present invention relates to an indole-based compound with excellent hole injection and hole transport ability; and to an organic electroluminescent device which includes the compound in one or more layers and thus has increased light emitting efficiency, needs lower driving voltages, and has an extended life span. According to the present invention, the electroluminescent device includes: (i) a positive electrode; (ii) a negative electrode; and (iii) one or more organic layers interposed between the positive electrode and the negative electrode.

Derisking the Cu-Mediated 18F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands

Molecules labeled with fluorine-18 (18F) are used in positron emission tomography to visualize, characterize and measure biological processes in the body. Despite recent advances in the incorporation of 18F onto arenes, the development of general and efficient approaches to label radioligands necessary for drug discovery programs remains a significant task. This full account describes a derisking approach toward the radiosynthesis of heterocyclic positron emission tomography (PET) radioligands using the copper-mediated 18F-fluorination of aryl boron reagents with 18F-fluoride as a model reaction. This approach is based on a study examining how the presence of heterocycles commonly used in drug development affects the efficiency of 18F-fluorination for a representative aryl boron reagent, and on the labeling of more than 50 (hetero)aryl boronic esters. This set of data allows for the application of this derisking strategy to the successful radiosynthesis of seven structurally complex pharmaceutically relevant heterocycle-containing molecules.

Total Syntheses of the Amaryllidaceae Alkaloids Zephycandidine III and Lycosinine A and Their Evaluation as Inhibitors of Acetylcholinesterase

The title alkaloids, 1 and 2, have been prepared using cross-coupling chemistries and together with various analogues they have been evaluated for their capacity to inhibit acetylcholinesterase. Contrary to an earlier report, it was found that biaryl 1 is not a significant inhibitor of this enzyme, and neither are any of its congeners, including alkaloid 2.

Preparation of No-Carrier-Added 6-[18F]Fluoro-l-tryptophan via Cu-Mediated Radiofluorination

18F-Labeled aromatic amino acids exhibit great potential for diagnostic applications using positron emission tomography. However, the introduction of18F into aromatic compounds remains challenging, and novel fluorination methods facilitating easy access to18F-labeled arenes are highly sought after. In recent years, novel metal-mediated fluorination methods have been reported and transferred into radiochemistry. Based on Cu-mediated radiofluorination, a two-step synthesis of no-carrier-added (n.c.a.) 6-[18F]fluoro-l-tryptophan was developed. 6-[18F]Fluoro-l-tryptophan was synthesized with an overall radochemical yield of 16 ± 4% within 110 min and a specific activity of 280 GBq μmol–1. The radiochemical purity was more than 99 %. The developed method allowed access to radiofluorinated tryptophan derivatives in high radiochemical yields and opens new ways to provide radiofluorinated amino acids. Furthermore, the reaction conditions were optimized to facilitate automation.