476004-82-7

Basic information

• Product Name: N-TIPS indole-3-boronic acid pinacol ester
• Synonyms: N-TIPS indole-3-boronic acid pinacol ester;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-indole;3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-triisopropylsilanyl-1H-indole
• CAS NO: 476004-82-7
• Molecular Formula: C₂₃H₃₈BNO₂Si
• Molecular Weight: 399.44982
• Mol File: 476004-82-7.mol

Chemical Properties

• Appearance: White to off-white, pinkish/Crystalline Powder
• CAS DataBase Reference: N-TIPS indole-3-boronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-TIPS indole-3-boronic acid pinacol ester(476004-82-7)
• EPA Substance Registry System: N-TIPS indole-3-boronic acid pinacol ester(476004-82-7)

Safety Data

• Hazardous Substances Data: 476004-82-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-TIPS indole-3-boronic acid pinacol ester is used as a reagent for the preparation of various organic compounds, facilitating the synthesis of a wide range of molecules.
Used in Pharmaceutical Synthesis:
N-TIPS indole-3-boronic acid pinacol ester is used as a key intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Synthesis:
N-TIPS indole-3-boronic acid pinacol ester is used as a key intermediate in the synthesis of agrochemicals, aiding in the creation of effective pesticides and other agricultural products.
Used in Biological Research:
N-TIPS indole-3-boronic acid pinacol ester is used as a valuable compound in biological research due to its reported interesting biological activities, which can lead to new insights and applications in the life sciences.

Upstream product

• 120-72-9 indole 
• 13154-24-0 triisopropylsilyl chloride 
• 148249-36-9 3-bromo-1-(1,1,1-triisopropylsilyl)-1H-indole 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 55718-76-8 2-chloro-1,3,2-benzodioxaborole 
• 123191-00-4 1-(triisopropylsilyl)-1H-indole 

Downstream Products

• 937366-54-6 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 

Relevant articles and documents

Catalytic Friedel–Crafts C?H Borylation of Electron-Rich Arenes: Dramatic Rate Acceleration by Added Alkenes

In the electrophilic C?H borylation of electron-rich aromatic compounds with catecholborane, the catalytic generation of the boron electrophile is initiated by heterolysis of the B?H bond by various Lewis and Br?nsted acids, with a boronium ion formed exclusively. After ligand dissociation, the corresponding borenium ion undergoes regioselective electrophilic aromatic substitution on aniline derivatives as well as nitrogen-containing heterocycles. The catalysis is optimized using B(C6F5)3 as the initiator and proceeds without the addition of an external base or dihydrogen acceptor. Temperatures above 80 °C are generally required to secure efficient turnover in these Friedel–Crafts-type reactions. Mechanistic experiments reveal that regeneration of the boronium/borenium ion with dihydrogen release is rate-determining. This finding finally led to the discovery that, with added alkenes, catalytic C?H borylations can, for the first time, be carried out at room temperature.

4-Substituted Pyrrolo[2,3-d]pyrimidine Compound and Use Thereof

The invention relates to a 4-substituted pyrrolo[2,3-d]pyrimidine compound and the use thereof in preparing medications for treating JAK-targeted diseases such as rheumatoid, immune system diseases, and tumor. The 4-substituted pyrrolo[2,3-d]pyrimidine compound of the invention is as shown in chemical formula I. The activity experimental results of the invention show that the new compound has obvious effect and activity in inhibition of Janus kinases, JAK-STAT, cell proliferation of human lymphocytoma, and rheumatoid arthritis.

PROCESS FOR THE BORYLATION OF ARENES AND HETEROARYLS

This invention relates to a novel process for the borylation of arenes and heteroaryls. The present invention also provides novel borenium cations, which act as electrophiles for electrophilic substitution on the arene or heteroaryl ring, as well as to methodology for the preparation of these cations.

Pinacol boronates by direct arene borylation with borenium cations

Borenium does it direct: A boron analogue of the Friedel-Crafts reaction uses inexpensive catecholatoborenium cations that are sufficiently electrophilic to borylate arenes by electrophilic aromatic substitution. The direct arene borylation proceeds with high regioselectivity for a range of anilines, N-heterocycles, and thiophenes. Subsequent one-pot transesterification provides the synthetically useful pinacol boronate esters (see scheme).

Simple inexpensive boron electrophiles for direct arene borylation

Electrophilic direct borylation is facilitated, and arene substrate scope enhanced, by using electrophiles derived from inexpensive reagents; specifically an amine, BCl3 and AlCl3.

PROCESS FOR PRODUCTION OF HETEROARYL-TYPE BORON COMPOUNDS WITH IRIDIUM CATALYST

The present invention provides an economically and industrially superior simple process that enables the selective production of an aromatic heterocyclic monoboron compound and aromatic heterocyclic diboron compound at a satisfactory yield and in a desired ratio by reacting an aromatic heterocyclic compound and a boron compound in a single step under mild conditions while changing only the charged ratios of the raw materials. The present invention provides a production process of a heteroaryl mono- or diboron compound comprising an aromatic heterocyclic compound and a boron compound in the form of bis(pinacolate)diboron or pinacolate diborane in the presence of a iridium-containing catalyst and a ligand such as a bipyridyl ligand.

Iridium-catalyzed C-H coupling reaction of heteroaromatic compounds with bis(pinacolato)diboron: Regioselective synthesis of heteroarylboronates

The C-H coupling of aromatic heterocycles with bis(pinacolato)diboron was carried out in octane at 80-100°C in the presence of a 1/2[IrCl(COD)]2-(4,4′-di-tert-butyl-2,2′-bipyridine) catalyst (3 mol%). The reactions of five-membered substrates such as thiophene, furan, pyrrole, and their benzo-fused derivatives exclusively produced 2-borylated products, whereas those of six-membered heterocycles including pyridine and quinoline selectively occurred at the 3-position. Regioselective synthesis of bis(boryl)heteroaromatics was also achieved by using an almost equimolar amount of substrates and the diboron.