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5-BROMO-1-TRIISOPROPYLSILANYL-1H-PYRROLO[2,3-B]PYRIDINE is a brominated pyrrolopyridine derivative with a molecular formula C15H24BrN2Si. It features a triisopropylsilyl group and is widely used in organic synthesis and medicinal chemistry for creating new molecular entities with potential biological activity. Its unique structure and the triisopropylsilyl group's ability to protect sensitive functional groups make it a versatile building block for developing pharmaceuticals and agrochemicals.

858116-66-2

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858116-66-2 Usage

Uses

Used in Organic Synthesis:
5-BROMO-1-TRIISOPROPYLSILANYL-1H-PYRROLO[2,3-B]PYRIDINE is used as a building block for the synthesis of complex organic molecules. Its unique structure and the triisopropylsilyl group's protective function make it a valuable tool in this field.
Used in Medicinal Chemistry:
In the pharmaceutical industry, 5-BROMO-1-TRIISOPROPYLSILANYL-1H-PYRROLO[2,3-B]PYRIDINE is used as a starting material for the development of new molecular entities with potential biological activity. Its versatile structure allows for the creation of compounds with therapeutic properties.
Used in Agrochemicals:
5-BROMO-1-TRIISOPROPYLSILANYL-1H-PYRROLO[2,3-B]PYRIDINE is also utilized in the agrochemical industry for the synthesis of compounds with pesticidal or herbicidal properties, contributing to the development of effective crop protection agents.
Overall, 5-BROMO-1-TRIISOPROPYLSILANYL-1H-PYRROLO[2,3-B]PYRIDINE is a valuable chemical compound with a wide range of applications in various fields of chemistry, including organic synthesis, medicinal chemistry, and agrochemicals, due to its unique structure and the versatility of its triisopropylsilyl group.

Check Digit Verification of cas no

The CAS Registry Mumber 858116-66-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,5,8,1,1 and 6 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 858116-66:
(8*8)+(7*5)+(6*8)+(5*1)+(4*1)+(3*6)+(2*6)+(1*6)=192
192 % 10 = 2
So 858116-66-2 is a valid CAS Registry Number.
InChI:InChI=1/C16H25BrN2Si/c1-11(2)20(12(3)4,13(5)6)19-8-7-14-9-15(17)10-18-16(14)19/h7-13H,1-6H3

858116-66-2 Well-known Company Product Price

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  • Aldrich

  • (ADE000903)  5-Bromo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine  AldrichCPR

  • 858116-66-2

  • ADE000903-1G

  • 7,411.95CNY

  • Detail

858116-66-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-Bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

1.2 Other means of identification

Product number -
Other names (5-bromopyrrolo[2,3-b]pyridin-1-yl)-tri(propan-2-yl)silane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:858116-66-2 SDS

858116-66-2Downstream Products

858116-66-2Relevant articles and documents

Novel BCL-2/BCL-XL inhibitor, pharmaceutical composition and application

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Paragraph 0045-0048; 0062-0063, (2020/11/12)

The invention relates to a compound for inhibiting the activity of Bcl-2/BCL-XL anti-apoptotic protein, a composition containing the compound and application of the compound serving as a synthetic drug, in particular to application of the compound serving as a drug for synthesizing a Bcl-2/BCL-XL anti-apoptotic protein inhibitor and application of the compound to cancer.

Preparation method of Venetoclax intermediate and product

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Paragraph 0040-0043; 0050-0053, (2019/02/25)

The invention discloses a preparation method of a Venetoclax intermediate. 5-bromine-7-azaindole (II) is used as a raw material; an upper protecting group generates 5-bromine-1-(Triisopropyl silicyl)-1H-pyrrolo[2,3-b]pyridine (III); a compound (III) and T

Solid dispersions containing an apoptosis-inducing agent

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Page/Page column 12, (2019/03/15)

A pro-apoptotic solid dispersion comprises, in essentially non-crystalline form, a Bcl-2 family protein inhibitory compound of Formula I as defined herein, dispersed in a solid matrix that comprises (a) a pharmaceutically acceptable water-soluble polymeric carrier and (b) a pharmaceutically acceptable surfactant. A process for preparing such a solid dispersion comprises dissolving the compound, the polymeric carrier and the surfactant in a suitable solvent, and removing the solvent to provide a solid matrix comprising the polymeric carrier and the surfactant and having the compound dispersed in essentially non-crystalline form therein. The solid dispersion is suitable for oral administration to a subject in need thereof for treatment of a disease characterized by overexpression of one or more anti-apoptotic Bcl-2 family proteins, for example cancer.

Method for preparing 5-hydroxy-7-azaindole

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Paragraph 0050-0053; 0075-0078; 0095-0100, (2017/12/28)

The invention discloses a method for preparing 5-hydroxy-7-azaindole. The intermediate structure is shown in the formula III. The method comprises that a compound 5-bromo-7-azaindole shown in the formula I as a raw material undergoes a nitrogen protection reaction and a hydroxylation and direct deprotection reaction to produce 5-hydroxy-7-azaindole shown in the formula III. The method utilizes cheap and easily available raw materials, realizes a low cost, is used under mild reaction conditions, has a high yield and is suitable for industrial large-scale production.

PYRIMIDINE AND PYRIDINE DERIVATIVES AND USE IN TREATMENT, AMELIORATION OR PREVENTION OF INFLUENZA THEREOF

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Page/Page column 106, (2017/12/28)

Provided herein is a compound of formula (I), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, prodrug, codrug, cocrystal, tautomer, racemate, enantiomer, or diastereomer or mixture thereof, which is useful in treating, ameliorating or preventing influenza.

THERAPEUTIC COMBINATIONS OF A BTK INHIBITOR, A PI3K INHIBITOR, A JAK-2 INHIBITOR, AND/OR A BCL-2 INHIBITOR

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Paragraph 00744, (2016/02/29)

Therapeutic combinations of a phosphoinositide 3-kinase (PI3K) inhibitor, including PI3K inhibitors selective for the γ- and δ-isoforms and selective for both γ- and δ-isoforms (PI3K-γ,δ, PI3K-γ, and PI3K-δ), a Janus kinase-2 (JAK-2) inhibitor, a Bruton's tyrosine kinase (BTK) inhibitor, and/or a B-cell lymphoma-2 (BCL-2) inhibitor are described. In some embodiments, the invention provides therapeutic combinations of a PI3K-δ inhibitor and a BTK inhibitor, a JAK-2 and a BTK inhibitor, and a BCL-2 and BTK inhibitor.

Novel fluorine-18 labeled 5-(1-pyrrolidinylsulfonyl)-7-azaisatin derivatives as potential PET tracers for in vivo imaging of activated caspases in apoptosis

Waldmann, Christopher M.,Hermann, Sven,Faust, Andreas,Riemann, Burkhard,Schober, Otmar,Sch?fers, Michael,Haufe, Günter,Kopka, Klaus

supporting information, p. 5734 - 5739 (2015/11/11)

The programmed type I cell death, defined as apoptosis, is induced by complex regulated signaling pathways that trigger the intracellular activation of executioner caspases-3, -6 and -7. Once activated, these enzymes initiate cellular death through cleavage of proteins which are responsible for DNA repair, signaling and cell maintenance. Several radiofluorinated inhibitors of caspases-3 and -7, comprising a moderate lipophilic 5-(1-pyrrolidinylsulfonyl)isatin lead structure, are currently being investigated for imaging apoptosis in vivo by us and others. The purpose of this study was to increase the intrinsic hydrophilicity of the aforementioned lead structure to alter the pharmacokinetic behavior of the resulting caspase-3 and -7 targeted radiotracer. Therefore, fluorinated and non-fluorinated derivatives of 5-(1-pyrrolidinylsulfonyl)-7-azaisatin were synthesized and tested for their inhibitory properties against recombinant caspases-3 and -7. Fluorine-18 has been introduced by copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) of an alkyne precursor with 2-[18F]fluoroethylazide. Using dynamic micro-PET biodistribution studies in vivo the kinetic behavior of one promising PET-compatible 5-pyrrolidinylsulfonyl 7-azaisatin derivative has been compared to a previously described isatin based radiotracer.

APOPTOSIS-INDUCING AGENTS FOR THE TREATMENT OF CANCER AND IMMUNE AND AUTOIMMUNE DISEASES

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Paragraph 0226, (2014/09/30)

Disclosed herein are compounds that inhibit the activity of anti-apoptotic Bcl-2 proteins, compositions containing the compounds and methods of treating diseases using the compounds.

A closer look at the bromine-lithium exchange with tert-butyllithium in an aryl sulfonamide synthesis

Waldmann, Christopher,Schober, Otmar,Haufe, Guenter,Kopka, Klaus

supporting information, p. 2954 - 2957 (2013/07/26)

A practical protocol for the one-pot synthesis of various aryl sulfonamides, notably of pyridine-core-substituted 7-azaindolyl sulfonamides, is described. A key step is the well-known bromine-lithium exchange reaction of an aryl bromide with tert-butyllithium (t-BuLi). Differing from the common practice to use 2 or more equiv of organolithium, the exact amount of t-BuLi needed for a sufficient exchange reaction is determined for each aryl bromide in a GC-MS-assisted experiment.

SALTS AND CRYSTALLINE FORMS OF AN APOPTOSIS-INDUCING AGENT

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Page/Page column 11, (2012/06/15)

Salts and crystalline forms of 4-(4-{[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-en-1-yl]methyl}piperazin-1-yl)-N-({3-nitro-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}- sulfonyl)-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzamide are suitable active pharmaceutical ingredients for pharmaceutical compositions useful in treatment of a disease characterized by overexpression of one or more anti-apoptotic Bcl-2 family proteins, for example cancer.

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