1259279-57-6

Basic information

• Product Name: 5-Fluoro-1-tosyl-7-azaindole-3-boronic acid pinacol ester
• Synonyms: 5-Fluoro-1-tosyl-7-azaindole-3-boronic acid pinacol ester;5-fluoro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine;1H-Pyrrolo[2,3-b]pyridine, 5-fluoro-1-[(4-methylphenyl)sulfonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;5-Fluoro-1-[(4-methylphenyl)sulfonyl]-7-azaindole-3-boronic acid pinacol ester;5-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine;EOS-60353
• CAS NO: 1259279-57-6
• Molecular Formula: C₂₀H₂₂BFN₂O₄S
• Molecular Weight: 434.2893632
• Mol File: 1259279-57-6.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 574.5±60.0 °C(Predicted)
• Appearance: /
• Density: 1.28±0.1 g/cm3(Predicted)
• Vapor Pressure: 0-0Pa at 20-25℃
• PKA: -1.05±0.30(Predicted)
• CAS DataBase Reference: 5-Fluoro-1-tosyl-7-azaindole-3-boronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Fluoro-1-tosyl-7-azaindole-3-boronic acid pinacol ester(1259279-57-6)
• EPA Substance Registry System: 5-Fluoro-1-tosyl-7-azaindole-3-boronic acid pinacol ester(1259279-57-6)

Safety Data

• Hazardous Substances Data: 1259279-57-6(Hazardous Substances Data)

Usage

General Description

5-Fluoro-1-tosyl-7-azaindole-3-boronic acid pinacol ester is a chemical compound that is used in organic synthesis and medicinal chemistry. It is a boronic acid derivative that contains a tosyl group and a fluorine atom, giving it unique properties for use in various reactions. Boronic acids are known for their ability to form strong bonds with carbon and oxygen atoms, making them useful in Suzuki-Miyaura coupling reactions and other organic transformations. The pinacol ester moiety provides stability and solubility, making the compound easier to handle and store. Overall, 5-Fluoro-1-tosyl-7-azaindole-3-boronic acid pinacol ester is a valuable building block for the synthesis of complex organic molecules and drug candidates.

Upstream product

• 866318-99-2 5-fluoro-1-tosyl-1H-pyrrolo [2,3-b]pyridine 
• 73183-34-3 bis(pinacol)diborane 
• 869557-43-7 3-bromo-5-fluoropyridin-2-amine 
• 936344-74-0 3-ethynyl-5-fluoro-pyridin-2-ylamine 
• 866319-00-8 5-fluoro-1H-pyrrolo[2,3‐b]pyridine 
• 21717-96-4 2-amino-5-fluoropyridine 
• 823218-51-5 5-fluoro-3-iodo-pyridin-2-amine 
• 866319-01-9 5-fluoro-3-(2-trimethylsilylethynyl)pyridine-2-amine 
• 1190309-71-7 3-bromo-5-fluoro-1H-pyrrolo-[2,3-b]pyridine 
• 98-59-9 p-toluenesulfonyl chloride 
• 1417421-99-8 3-bromo-5-fluoro-1-(p-toluenesulfonyl)-1H-pyrrolo[2,3-b]pyridine 

Downstream Products

• 1383375-16-3 3-(2-chloro-5-fluoropyrimidin-4-yl)-5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridine 
• 1383375-54-9 (1S,3S)-N₁-(3,5-difluoro-6-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-yl)cyclohexane-1,3-diamine 
• 1383375-56-1 N-((1R,3S)-3-((3,5-difluoro-6-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-yl)amino)cyclohexyl)pyrrolidine-1-carboxamide 
• 1383375-52-7 5-fluoro-1-tosyl-3-(3,5,6-trifluoropyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine 
• 1383375-60-7 tert-butyl ((1R,3S)-3-((5-cyano-3-fluoro-6-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-yl)amino)cyclohexyl)carbamate 

Relevant articles and documents

Discovery of VX-509 (Decernotinib): A Potent and Selective Janus Kinase 3 Inhibitor for the Treatment of Autoimmune Diseases

While several therapeutic options exist, the need for more effective, safe, and convenient treatment for a variety of autoimmune diseases persists. Targeting the Janus tyrosine kinases (JAKs), which play essential roles in cell signaling responses and can contribute to aberrant immune function associated with disease, has emerged as a novel and attractive approach for the development of new autoimmune disease therapies. We screened our compound library against JAK3, a key signaling kinase in immune cells, and identified multiple scaffolds showing good inhibitory activity for this kinase. A particular scaffold of interest, the 1H-pyrrolo[2,3-b]pyridine series (7-azaindoles), was selected for further optimization in part on the basis of binding affinity (Ki) as well as on the basis of cellular potency. Optimization of this chemical series led to the identification of VX-509 (decernotinib), a novel, potent, and selective JAK3 inhibitor, which demonstrates good efficacy in vivo in the rat host versus graft model (HvG). On the basis of these findings, it appears that VX-509 offers potential for the treatment of a variety of autoimmune diseases.

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