942070-45-3

Usage

Uses

Used in Pharmaceutical Synthesis:
1-BOC-indole-3-boronic acid, pinacol ester is used as a reagent for the introduction of the indole moiety into various molecules, playing a crucial role in the development of new pharmaceuticals. Its mild reactivity and the ease of deprotection of the BOC group allow for the synthesis of complex molecules with the indole structure, which is common in many bioactive compounds and drugs.
Used in Agrochemical Development:
In the agrochemical industry, 1-BOC-indole-3-boronic acid, pinacol ester is utilized as a key intermediate for the synthesis of agrochemicals with the indole framework. The versatility of 1-BOC-indole-3-boronic acid, pinacol ester enables the creation of molecules with potential applications in pest control and crop protection, contributing to the development of more effective and environmentally friendly agrochemicals.
Used in Organic Synthesis:
1-BOC-indole-3-boronic acid, pinacol ester is employed as a versatile building block in organic synthesis. Its unique structure and reactivity make it suitable for a wide range of applications, including the synthesis of natural products, the development of new synthetic methods, and the creation of novel functional materials. The BOC protecting group further enhances its utility by allowing for selective reactions and the construction of complex molecular architectures.

InChI:InChI=1/C13H18O/c1-13(2,3)12-8-6-11(7-9-12)5-4-10-14/h6-10H,4-5H2,1-3H3

Upstream product

• 75400-67-8 indole-1-carboxylic acid tert-butyl ester 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 192189-07-4 tert-butyl 3-iodo-1H-indol-1-carboxylate 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 73183-34-3 bis(pinacol)diborane 
• 24424-99-5 di-tert-butyl dicarbonate 
• 26340-47-6 3-Iodo-1H-indole 
• 120-72-9 indole 
• 143259-56-7 3-bromoindole-1-carboxylic acid tert-butyl ester 

Downstream Products

• 937366-54-6 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 
• 1020176-83-3 3-(4-{(S)-1-[(R)-1-(4-Methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridin-2-yl)-indole-1-carboxylic acid tert-butyl ester 
• 289628-76-8 4-(1H-indol-3-yl)pyrimidin-2-amine 
• 1146080-39-8 3-(pyrimidin-2-yl)-1H-indole 
• 1426414-50-7 (S)-tert-butyl 3-(1-hydroxy-1-phenylethyl)-1H-indole-1-carboxylate 
• 135531-86-1 camalexin 

Relevant academic research and scientific papers

Photoassisted Cross-Coupling Reaction of α-Chlorocarbonyl Compounds with Arylboronic Acids

A Suzuki-Miyaura cross-coupling reaction of α-chloroacetates or α-chloroacetamides with arylboronic acids is made possible by visible-light irradiation. This reaction provides a useful method for the synthesis of α-arylacetates and α-arylacetamides from chlorides under mild reaction conditions. An indole-3-acetic acid derivative that is the key intermediate of the plant hormone auxin can be synthesized from 1-Boc-indole in two steps by combining an iridium-catalyzed C-H borylation and a palladium-catalyzed cross-coupling reaction.

Tricepyridinium-inspired QACs yield potent antimicrobials and provide insight into QAC resistance

Quaternary ammonium compounds (QACs) comprise a large class of surfactants, consumer products, and disinfectants. The recently-isolated QAC natural product tricepyridinium bromide displays potent inhibitory activity against S. aureus but due to its unique structure, its mechanism of action remains unclear. A concise synthetic route to access tricepyridinium analogs was thus designed and four N-alkyl compounds were generated in addition to the natural product. Biological analysis of these compounds revealed that they display remarkable selectivity towards clinically-relevant Gram-positive bacteria exceeding that of commercially-available QACs such as cetylpyridinium chloride (CPC) and benzalkonium chloride (BAC) while having little to no hemolytic activity. Molecular modeling studies revealed that tricepyridinium and shorter-chain N-alkyl analogs may preferentially bind to the QacR transcription factor leading to potential activation of the QAC resistance pathway found in MRSA; however, our newly synthesized analogs are able to overcome this liability.

Small-molecule anti-HIV-1 agents based on HIV-1 capsid proteins

The capsid of human immunodeficiency virus type 1 (HIV-1) is a shell that encloses viral RNA and is highly conserved among many strains of the virus. It forms a conical structure by assembling oligomers of capsid (CA) proteins. CA dysfunction is expected to be an important target of suppression of HIV-1 replication, and it is important to understand a new mechanism that could lead to the CA dysfunction. A drug targeting CA however, has not been developed to date. Hydrophobic interactions between two CA molecules via Trp184/Met185 in CA were recently reported to be important for stabilization of the multimeric structure of CA. In the present study, a small molecule designed by in silico screening as a dipeptide mimic of Trp184 and Met185 in the interaction site, was synthesized and its significant anti-HIV-1 activity was confirmed. Structure activity relationship (SAR) studies of its derivatives were performed and provided results that are expected to be useful in the future design and development of novel anti-HIV agents targeting CA.

Understanding the Activation of Air-Stable Ir(COD)(Phen)Cl Precatalyst for C-H Borylation of Aromatics and Heteroaromatics

A newly developed robust catalyst [Ir(COD)(Phen)Cl] (A) was used for the C-H borylation of three dozen aromatics and heteroaromatics with excellent yield and selectivity. Activation of the catalyst was identified by the use of catalytic amounts of water, alcohols, etc., when B2pin2 was used in noncoordinating solvents, while for THF catalytic use of HBpin was required. The results were on par with the in situ based expensive system [Ir(OMe)(COD)]2/dtbbpy or Me4Phen.

Hyrtinadine alkaloid derivative as well as preparation and application of Hyrtinadine alkaloid derivative in resisting plant viruses and germs

The invention relates to a Hyrtinadine alkaloid derivative as well as preparation and application of the Hyrtinadine alkaloid derivative in resisting plant viruses and germs. The Hyrtinadine alkaloidderivative shows especially excellent plant virus resist

Two Ligands Transfer from Ag to Pd: En Route to (SIPr)Pd(CF2H)(X) and Its Application in One-Pot C-H Borylation/Difluoromethylation

A process for the concurrent transfer of both the NHC ligand and the difluoromethyl group from [(SIPr)Ag(CF2H)] to PdX2 (X = Cl, OAc, and OPiv) for the preparation of [(SIPr)Pd(CF2H)X] complexes is described. These complexes were air-stable and easily underwent transmetalation with aryl pinacol boronate/reductive elimination to generate ArCF2H in high yields. Based on this discovery, the first one-pot C-H borylation and difluoromethylation process for the preparation of difluoromethylated (hetero)arenes was developed.

BENZYLAMINE COMPOUND, AND PHARMACEUTICAL COMPOSITION AND ANTI-HIV AGENT THEREOF

PROBLEM TO BE SOLVED: To provide: a novel benzylamine compound; and a pharmaceutical composition and an anti-HIV agent that are suitable for suppression of HIV activity. SOLUTION: The benzylamine compound is represented by the general formula (1) in the figure. In the general formula (1), R1 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; A represents an oxygen atom or sulfur atom; R2 represents a substituted or unsubstituted alkyl group; and n represents an integer from 1 to 10. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

Double N,B-Type Bidentate Boryl Ligands Enabling a Highly Active Iridium Catalyst for C-H Borylation

Boryl ligands hold promise in catalysis due to their very high electron-donating property. In this communication double N,B-type boryl anions were designed as bidentate ligands to promote an sp2 C-H borylation reaction. A symmetric pyridine-con

Iridium-catalyzed C-H borylation of heterocycles using an overlooked 1,10-phenanthroline ligand: Reinventing the catalytic activity by understanding the solvent-assisted neutral to cationic switch

The preformed catalyst [Ir(Cl)(COD)(1,10-phenanthroline)] (2; COD = cyclooctadiene) was found to be highly effective in a model reaction for the borylation of N-Boc-indole at the 3-position with B2pin2 (pin = pinacolato) as the borylating agent to give consistently 99% yield with 0.5 mol % catalyst loading. The corresponding in situ formed catalyst from [Ir(Cl)(COD)]2 and 1,10-phenanthroline provided very inconsistent results for the same reaction (0-94% conversion). We propose this to be due to the competing formation of a catalytically inactive cationic complex, [Ir(COD)(1,10-phenanthroline)]+Cl- (1), in a noncoordinating solvent such as octane. Complexes 1 and 2 were characterized using solid-state NMR (13C and 35Cl) in conjunction with XPS to be cationic and neutral, respectively. The X-ray crystal structure of a pentavalent neutral Ir complex, [Ir(Cl)(COD)(2,2′-bipyridine)] (3), was also obtained for comparison purposes. Using catalyst 2, the total synthesis of Meridianin G was accomplished in 87% overall isolated yield in a one-pot, three-step process.

Asymmetric synthesis of 1-heteroaryl-1-arylalkyl tertiary alcohols and 1-pyridyl-1-arylethanes by lithiation-borylation methodology

The synthesis of highly enantioenriched α-heterocyclic tertiary alcohols has been achieved via lithiation-borylation of a configurationally stable lithiated carbamate and heterocyclic pinacol boronic esters followed by oxidation. Protodeboronation of the α-heterocyclic tertiary boronic esters using TBAF·3H2O or CsF gave highly enantioenriched 1-pyridyl-1-arylethanes in high er.