866546-10-3

Basic information

• Product Name: 1H-Pyrrolo[2,3-b]pyridine, 3-bromo-5-chloro-1-[(4-methylphenyl)sulfonyl]-
• Synonyms: 1H-Pyrrolo[2,3-b]pyridine, 3-bromo-5-chloro-1-[(4-methylphenyl)sulfonyl]-;3-bromo-5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine;3-bromo-5-chloro-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridine;3-Bromo-5-chloro-1-(toluene-4-sulphonyl)-7-azaindole
• CAS NO: 866546-10-3
• Molecular Formula: C₁₄H₁₀BrClN₂O₂S
• Molecular Weight: 385.67
• Mol File: 866546-10-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 527°C at 760 mmHg
• Flash Point: 272.5°C
• Appearance: /
• Density: 1.68g/cm³
• Vapor Pressure: 3.4E-11mmHg at 25°C
• Refractive Index: 1.695
• CAS DataBase Reference: 1H-Pyrrolo[2,3-b]pyridine, 3-bromo-5-chloro-1-[(4-methylphenyl)sulfonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrolo[2,3-b]pyridine, 3-bromo-5-chloro-1-[(4-methylphenyl)sulfonyl]-(866546-10-3)
• EPA Substance Registry System: 1H-Pyrrolo[2,3-b]pyridine, 3-bromo-5-chloro-1-[(4-methylphenyl)sulfonyl]-(866546-10-3)

Safety Data

• Hazardous Substances Data: 866546-10-3(Hazardous Substances Data)

Usage

Class

pyrrolopyridine derivatives

Structure

pyrrolo[2,3-b]pyridine ring system

Substitution

bromo-chloro at the 3 and 5 positions

Functional group

sulfonyl group attached to the 1 position

Use

building block in the synthesis of organic molecules and pharmaceuticals

Potential

biological activity and reactivity

Applications

medicinal chemistry and drug discovery.

InChI:InChI=1/C14H10BrClN2O2S/c1-9-2-4-11(5-3-9)21(19,20)18-8-13(15)12-6-10(16)7-17-14(12)18/h2-8H,1H3

Upstream product

• 866546-07-8 5-chloro-1H-pyrrolo[2,3-b]pyridine 
• 866318-90-3 2-amino-5-chloro-3-[(trimethylsilyl)ethynyl]pyridine 
• 211308-81-5 5-chloro-3-iodo-2-aminopyridine 
• 1072-98-6 5-chloro-2-pyridylamine 
• 866546-09-0 3-bromo-5-chloro-1 H-pyrrolo[2,3-b]pyridine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 1346172-63-1 (2S,3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-(6-(5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)azetidine-2-carboxamide 
• 1346172-68-6 tert-butyl (3R)-4-(6-{5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrazin-2-yl)-3-[(2,2,2-trifluoroethyl)carbamoyl]piperazine-1-carboxylate 
• 1346172-70-0 (2R)-1-(6-{5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)piperazine-2-carboxamide hydrochloride 
• 1346172-78-8 2-(3-{5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine-3-yl}-5H-pyrrolo[2,3-b]pyrazin-5-yl)-N-(2,2,2-trifluoroethyl)acetamide 
• 1346172-81-3 methyl 1-[(6-{5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-pyrazin-2-yl)oxy]cyclopropanecarboxylate 
• 1346172-89-1 methyl 6-{5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-pyrazine-2-carboxylate 
• 1346172-93-7 diethyl (6-{5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-pyrazin-2-yl)propanedioate 
• 1363407-75-3 potassium (5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)trifluoroborate 
• 1346172-28-8 tert-butyl N-{6-[5-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrazin-2-yl}-L-alaninate 
• 1346172-29-9 N-{6-[5-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrazin-2-yl}-L-alanine 
• 1346172-30-2 N₂-{6-[5-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrazin-2-yl}-N-(2,2,2-trifluoroethyl)-L-alaninamide 
• 1422051-72-6 (R)-3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-pyrimidin-4-ylamino)-4,4-dimethylpentanoic acid 

Relevant articles and documents

PYRROLO[2,3-B]PYRIDIN DERIVATIVES AS INHIBITORS OF INFLUENZA VIRUS REPLICATION

Provided herein are compounds of Formula A, B or C that can inhibit the replication of influenza viruses, reduce the amount of influenza viruses, and/or treat influenza.

PYRROLOPYRIMIDINE DERIVATIVES USEFUL AS INHIBITORS OF INFLUENZA VIRUS REPLICATION

Methods of inhibiting the replication of influenza viruses in a biological sample or patient, of reducing the amount of influenza viruses in a biological sample or patient, and of treating influenza in a patient, comprises administering to said biological sample or patient a safe and effective amount of a compound represented by any of Formulas l-lll, or a pharmaceutically acceptable salt thereof. A pharmaceutical composition comprises a safe and effective amount of such a compound or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, adjuvant or vehicle.

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.