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
• Article Data: 18

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 
• 1456507-76-8 (4S)-3-(4-(1H-pyrrolo[2,3-b]pyridin-5-yl)cyclohex-3-en-1-yl)-5,5-dimethyl-4-phenyloxazolidin-2-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.

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.

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.