754214-56-7

Basic information

• Product Name: 5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1H-PYRROLO[2,3-B]PYRIDINE
• Synonyms: 5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1H-PYRROLO[2,3-B]PYRIDINE;1H-Pyrrolo[2,3-b]pyridine, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;7-Azaindole-5-boronic acid pinacol ester;Pyrrolo[2,3-b)pyridine-5-boronic acid,pinacol ester;7-Azaindole-5-boronic aci...;5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1;5-(tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine;1H-Pyrrolo[2,3-B]pyridine-5-boronic acid pinacol ester
• CAS NO: 754214-56-7
• Molecular Formula: C₁₃H₁₇BN₂O₂
• Molecular Weight: 244.1
• Product Categories: Heteroaryl Boronate Esters;Boronate Esters;Boronic Acids and Derivatives;Chemical Synthesis;New Products for Chemical Synthesis;Organometallic Reagents;Organic boronic acid
• Mol File: 754214-56-7.mol

Chemical Properties

• Melting Point: 242-242.5°C
• Appearance: /
• Density: 1.154 g/cm³
• Refractive Index: 1.573
• Storage Temp.: ?20°C
• Solubility: Soluble in methanol, ethanol and THF.
• PKA: 13.88±0.40(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: 5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1H-PYRROLO[2,3-B]PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1H-PYRROLO[2,3-B]PYRIDINE(754214-56-7)
• EPA Substance Registry System: 5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1H-PYRROLO[2,3-B]PYRIDINE(754214-56-7)

Safety Data

• Hazard Codes: Xi,T,Xn
• Statements: 25-20/21/22-36/37/38
• Safety Statements: 45-36-22-37-26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 754214-56-7(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

7-Azaindole-5-boronic acid pinacol ester is used as pharmaceutical intermediate.

InChI:InChI=1/C13H19BN2O3/c1-12(2,17)13(3,4)19-14(18)10-7-9-5-6-15-11(9)16-8-10/h5-8,17-18H,1-4H3,(H,15,16)

Upstream product

• 73183-34-3 bis(pinacol)diborane 
• 183208-35-7 5-bromo-1H-pyrrolo[2,3-b]pyridine 
• 271-63-6 7-Azaindole 
• 866546-07-8 5-chloro-1H-pyrrolo[2,3-b]pyridine 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 121-43-7 Trimethyl borate 
• 10592-27-5 7-azaindoline 
• 115170-40-6 7-aza-5-bromoindoline 

Downstream Products

• 849069-56-3 [4-(1H-pyrrolo[2,3-b]pyridin-5-yl)-cyclohex-3-enyl]-carbamic acid tert-butyl ester 
• 1111636-35-1 3-((4-(1-(2,2-difluoroethyl)-3-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazol-4-yl)pyrimidin-2-yl)amino)propanenitrile 
• 1220696-34-3 (S)-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine 
• 1310530-10-9 1-tert-butyl-2-[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]-5-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-benzimidazole 
• 1312312-76-7 2-chloro-4-(1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 1312942-04-3 propane-1-sulfonic acid {2,4-difluoro-3-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl}-amide 
• 1312939-70-0 propane-1-sulfonic acid {2,4-difluoro-3-[5-(1H-pyrazolo[3,4-b]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl}-amide 
• 1312942-05-4 N-(3-(1-(2,6-dichlorobenzoyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)propane-1-sulfonamide 
• 1312940-07-0 propane-1-sulfonic acid {2,4-difluoro-3-[5-(1-pyrimidin-2-yl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl}-amide 
• 1312942-03-2 propane-1-sulfonic acid (2,4-difluoro-3-{hydroxy-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-methyl}-phenyl)-amide 
• 1415388-32-7 C₂₀H₁₇N₃O₃ 
• 1428335-27-6 C₃₀H₂₄N₆O₃ 
• 1428335-52-7 C₃₀H₂₄N₆O₃ 
• 1416000-43-5 2-(1H-pyrrolo[2,3-b]pyridin-5-yl)-10-(3-(trifluoromethyl)phenyl)pyrido[3,2-c][1,5] naphthyridin-9(10H)-one 

Relevant articles and documents

Development of anti-breast cancer PI3K inhibitors based on 7-azaindole derivatives through scaffold hopping: Design, synthesis and in vitro biological evaluation

Breast cancer is the cancer with the highest incidence all over the world. Phosphatidylinositol 3-kinase is an important regulator of intracellular signaling pathways, which is frequently mutated and overexpressed in majority of human breast cancers, and the inhibition of PI3K has been considered as a promising approach for the treatment of the cancer. Here, we report our design and synthesis of new 7-azaindole derivatives as PI3K inhibitors through the scaffold hopping strategy. By varying the groups at the 3-position of 7-azaindole, we identified a series of potent PI3K inhibitors, whose antiproliferative activities against two human breast cancer MCF-7 and MDA-MB-231 cell lines were evaluated. Representative derivatives FD2054 and FD2078 showed better activity than BKM120 in antiproliferation, reduced the levels of phospho-AKT and induced cell apoptosis. All these results suggested that FD2054 and FD2078 are potent PI3K inhibitors that could be considered as potential candidates for the development of anticancer agents.

AZAINDOLE DERIVATIVE AND USE THEREOF AS FGFR AND C-MET INHIBITOR

A series of pyrazolopymidine derivatives, and use thereof in the preparation of a medicament for treating disease associated with FGFR and c-Met. The pyrazolopymidine derivative is a compound represented by formula (I), a tautomer, or a pharmaceutically acceptable salt thereof.

A Monophosphine Ligand Derived from Anthracene Photodimer: Synthetic Applications for Palladium-Catalyzed Coupling Reactions

Herein, we present an air-stable dianthracenyl monophosphine ligand (diAnthPhos) which can be prepared in two steps from commercially available anthracene derivatives. The ligand exhibits excellent efficiency for palladium-catalyzed coupling reactions. In particular, Miyaura borylation of heterocycle-containing electrophiles can be facilitated employing the diAnthPhos ligand with a broad substrate scope and low catalyst loading. The valuable synthetic utility of the new ligand is further demonstrated by a one-pot Miyaura borylation/Suzuki coupling protocol for heteroaryl-containing substrates.

PYRROLO [2, 3-B] PYRIDINES OR PYRROLO [2, 3-B] PYRAZINES AS HPK1 INHIBITOR AND THE USE THEREOF

Disclosed herein is a compound of Formula (AIII) or (III), or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof, and pharmaceutical compositions comprising thereof. Also disclosed is a method of treating HPK1 related disorders or diseases by using the compound disclosed herein.

Heterocyclic boronic acid compound synthesis process

The invention relates to a synthetic process of a heterocyclic boric acid compound. The process comprises the following steps: carrying out reaction on 5-chloro-7-azaindole and tert-butyldimethylsilyl chloride in the presence of triethylamine to carry out posttreatment to obtain a yellow solid; carrying out reaction on yellow solid and trimethyl borate in the presence of sodium carbonate to carry out post-treatment to obtain a yellow oily object; carrying out reaction on the yellow oily object and pinacol and concentrating to obtain a colorless oily object; and carrying out posttreatment on the colorless oily object to obtain a white solid to obtain 7-azaindole-pinacol boronate. Not only is the synthetic method provided by the invention yield and high in purity, but also the toxicity of the used chemical reagent is less, so that the damage on the operator is reduced, thereby facilitating industrial scaled production. The synthetic method is also suitable for synthesizing other heterocyclic boric acid compounds such as 7-azaindole-4-pinacol boronate, 7-azaindole-3-pinacol boronate and has an important application value.

Alkynyl compound and its method and use thereof

The invention provides a novel substituted alkynyl compound and its pharmaceutically acceptable salt and medicinal preparation, and a use of the novel substituted alkynyl compound and its pharmaceutically acceptable salt and medicinal preparation in adjustment of protein kinase activity and intercellular or intracellular signal response. The invention also relates to a pharmaceutical composition containing the novel substituted alkynyl compound and a method for treating high-proliferative diseases of mammals especially such as human by the pharmaceutical composition.

Method for synthesizing Venetoclax key intermediates

The invention discloses a method for synthesizing Venetoclax key intermediates. The method includes steps of (1), carrying out coupling reaction on 5-bromine-7-azaindole and bisdiboron in solvents under the effects of organic palladium catalysts and alkali, and carrying out after-treatment after the reaction is completely carried out so as to obtain 7-azaindole-5-pinacol borate; (2), carrying out hydrolysis reaction on the 7-azaindole-5-pinacol borate obtained at the step (1) under the effect of sodium perborate, and carrying out after-treatment after the reaction is completely carried out so as to obtain the Venetoclax key intermediates. The method has the advantages that the method is easy to implement, highly toxic reagents can be omitted, and the HPLC (high-performance liquid chromatography) purity of the Venetoclax key intermediates which are products obtained by the aid of the method is higher than 99%.

ORGANIC LIGHT-EMITTING COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING SAME

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Organic light emitting compd. and organic electroluminescence element using the same

The present invention relates to a novel indole-based compound having excellent hole injection and transport capabilities, light-emission, and other properties, and to an organic electroluminescent device the luminous efficiency, driving voltage, service life, and other characteristics of which are improved due to containing the compound in one or more organic material layers.

ALKYNYL COMPOUNDS AND METHODS OF USE

The present invention provides novel substituted alkynyl compounds, pharmaceutical acceptable salts and formulations thereof useful in modulating the protein tyrosine kinase activity, and in modulating cellular activities such as proliferation, differentiation, apoptosis, migration and invasion. The invention also provides pharmaceutically acceptable compositions comprising such compounds and methods of using the compositions in the treatment of hyperproliferative disorders in mammals, especially humans.