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

• 115170-40-6 7-aza-5-bromoindoline 
• 10592-27-5 7-azaindoline 
• 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 
• 73183-34-3 bis(pinacol)diborane 
• 183208-35-7 5-bromo-1H-pyrrolo[2,3-b]pyridine 

Downstream Products

• 1613333-49-5 5-(6-methoxypyridin-3-yl)-1-(phenylsulfonyl)-3-((trimethylsilyl)ethynyl)-1H-pyrrolo[2,3-b]pyridine 
• 1613333-48-4 3-iodo-5-(6-methoxypyridin-3-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2.3-b]pyridine 
• 1613168-82-3 N-[4-(piperazin-1-ylmethyl)-3-(trifluoromethyl)phenyl]-3-(4-{1H-pyrrolo[2,3-b]pyridin-5-yl}phenyl)propanamide 
• 1613168-78-7 N-{4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl}-3-(4-{1H-pyrrolo[2,3-b]pyridin-5-yl}phenyl)propanamide 
• 1613168-30-1 N-[4-(piperazin-1-ylmethyl)-3-(trifluoromethyl)phenyl]-2-(4-{1H-pyrrolo[2,3-b]pyridin-5-yl}phenoxy)acetamide 

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.

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.