1073354-51-4

Basic information

• Product Name: N-(p-Toluenesulfonyl)indole-3-boronic acid pinacol ester
• Synonyms: N-(p-Toluenesulfonyl)indole-3-boronic acid pinacol ester;1H-Indole, 1-[(4-methylphenyl)sulfonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
• CAS NO: 1073354-51-4
• Molecular Formula: C₂₁H₂₄BNO₄S
• Molecular Weight: 397.3
• Mol File: 1073354-51-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(p-Toluenesulfonyl)indole-3-boronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-(p-Toluenesulfonyl)indole-3-boronic acid pinacol ester(1073354-51-4)
• EPA Substance Registry System: N-(p-Toluenesulfonyl)indole-3-boronic acid pinacol ester(1073354-51-4)

Safety Data

• Hazardous Substances Data: 1073354-51-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-(p-Toluenesulfonyl)indole-3-boronic acid pinacol ester is used as a reagent for enhancing the reactivity of compounds in various chemical reactions. The tosyl group's ability to increase reactivity makes it a valuable component in the synthesis of complex organic molecules.
Used in Suzuki Coupling Reactions:
In the field of advanced organic synthesis, N-(p-Toluenesulfonyl)indole-3-boronic acid pinacol ester is used as a coupling agent for forming carbon-carbon bonds through the popular Suzuki coupling method. This reaction is crucial for the construction of more complex molecular structures.
Used in the Creation of Bioactive Molecules:
Due to the presence of the indole core, N-(p-Toluenesulfonyl)indole-3-boronic acid pinacol ester is used as a building block in the synthesis of bioactive molecules and natural products. The indole motif is a common structural element in many biologically active compounds, making N-(p-Toluenesulfonyl)indole-3-boronic acid pinacol ester a useful tool in medicinal chemistry and drug discovery.

Upstream product

• 26340-47-6 3-Iodo-1H-indole 
• 120-72-9 indole 
• 170456-80-1 3-iodo-1-tosyl-1-indole 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 98-59-9 p-toluenesulfonyl chloride 
• 31271-90-6 1-(p-toluenesulfonyl)-1H-indole 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 13637-37-1 1H,1'H-[3,3']biindolyl 
• 763138-83-6 1,1'-bis-(toluene-4-sulfonyl)-1H,1'H-[3,3']biindolyl 
• 36797-43-0 3-methyl-N-(p-toluenesulfonyl)indole 
• 1338575-78-2 tert-butyl 4-(1-tosyl-1H-indol-3-yl)pent-4-enoate 

Relevant articles and documents

Nature-Inspired (di)Azine-Bridged Bisindole Alkaloids with Potent Antibacterial in Vitro and in Vivo Efficacy against Methicillin-Resistant Staphylococcus aureus

Natural bisindole alkaloids such as Hyrtinadine A and Alocasin A, which are known to exhibit diverse bioactivities, provide promising chemical scaffolds for drug development. By optimizing the Masuda borylation-Suzuki coupling sequence, a library of various natural product-derived and non-natural (di)azine-bridged bisindoles was created. While unsubstituted bisindoles were devoid of antibacterial activity, 5,5′-chloro derivatives were highly active against methicillin-resistant Staphylococcus aureus (MRSA) and further Gram-positive pathogens at minimal inhibitory concentrations ranging from 0.20 to 0.78 μM. These compounds showed strong bactericidal killing effects but only moderate cytotoxicity against human cell lines. Furthermore, the two front-runner compounds 4j and 4n exhibited potent in vivo efficacy against MRSA in a mouse wound infection model. Although structurally related bisindoles were reported to specifically target pyruvate kinase in MRSA, antibacterial activity of 4j and 4n is independent of pyruvate kinase. Rather, these compounds lead to bacterial membrane permeabilization and cellular efflux of low-molecular-weight molecules.

Iridium(I)-Catalyzed C?H Borylation in Air by Using Mechanochemistry

Mechanochemistry has been applied for the first time to an iridium(I)-catalyzed C?H borylation reaction. By using either none or just a catalytic amount of a liquid, the mechanochemical C?H borylation of a series of heteroaromatic compounds proceeded in air to afford the corresponding arylboronates in good-to-excellent yields. A one-pot mechanochemical C?H borylation/Suzuki–Miyaura cross-coupling sequence for the direct synthesis of 2-aryl indole derivatives is also described. The present study constitutes an important milestone towards the development of industrially attractive solvent-free C?H bond functionalization processes in air.

Pyrimidine derivatives Anaplastic lymphoma kinase inhibitors

The invention belongs to the field of a medical technology and specifically relates to a pyrimidine derivative type anaplastic lymphoma kinase inhibitor as shown in the general formula (I) or its stereisomer, or its pharmaceutically acceptable salt, ester or solvate, wherein R1, R2, R3, R4, R5 and A ring are as defined in the specification. The invention also relates to a preparation method of the compounds, a pharmaceutic preparation and a pharmaceutical composition containing the compounds and an application of the compound or its stereisomer, or its pharmaceutically acceptable salt, ester or solvate in the preparation of medicines for treating and/or preventing diseases related to anaplastic lymphoma kinase-mediated cancer.

One-pot synthesis of camalexins and 3,3′-biindoles by the Masuda borylation-Suzuki arylation (MBSA) sequence

The Masuda borylation/Suzuki arylation (MBSA) sequence starting from N-protected 3-iodoindoles has successfully been extended to the coupling of five-membered heterocycles and indoles in the arylation step, which could not be achieved with previously developed MBSA methods. By this approach the one-pot nature of the method as well as the use of a simple catalyst system has been retained. The applicability of the method has been demonstrated by the facile synthesis of camalexins and 3,3′-biindoles, compounds of special interest due to their pronounced antifungal, antimicrobial and cytotoxic activities. The Masuda borylation/Suzuki arylation sequence furnishes in a concise one-pot manner camalexins and 3,3′-biindoles, compounds that show pronounced antifungal, antimicrobial, and cytotoxic activities. Copyright