866546-11-4

Basic information

• Product Name: 1H-Pyrrolo[2,3-b]pyridine, 5-chloro-1-[(4-Methylphenyl)sulfonyl]-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)
• Synonyms: 1H-Pyrrolo[2,3-b]pyridine, 5-chloro-1-[(4-Methylphenyl)sulfonyl]-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl);5-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine;5-Chloro-1-tosyl-7-azaindole-3-boronic acid pinacol ester;5-Chloro-1-[(4-methylbenzene)sulfonyl]-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine;5-Chloro-1-[(4-methylphenyl)sulfonyl]-7-azaindole-3-boronic acid pinacol ester
• CAS NO: 866546-11-4
• Molecular Formula: C₂₀H₂₂BClN₂O₄S
• Molecular Weight: 432.72868
• Mol File: 866546-11-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 584.5±60.0 °C(Predicted)
• Appearance: /
• Density: 1.31±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: -1.22±0.30(Predicted)
• CAS DataBase Reference: 1H-Pyrrolo[2,3-b]pyridine, 5-chloro-1-[(4-Methylphenyl)sulfonyl]-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrolo[2,3-b]pyridine, 5-chloro-1-[(4-Methylphenyl)sulfonyl]-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)(866546-11-4)
• EPA Substance Registry System: 1H-Pyrrolo[2,3-b]pyridine, 5-chloro-1-[(4-Methylphenyl)sulfonyl]-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)(866546-11-4)

Safety Data

• Hazardous Substances Data: 866546-11-4(Hazardous Substances Data)

Usage

General Description

1H-Pyrrolo[2,3-b]pyridine, 5-chloro-1-[(4-Methylphenyl)sulfonyl]-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl) is a chemical compound that contains a pyrrolopyridine core with a chloro-substituted sulfonyl group and a boronic ester. It is commonly used in organic synthesis for the production of pharmaceuticals and agrochemicals. The compound's unique structure and reactivity make it valuable for forming carbon-carbon and carbon-heteroatom bonds, making it an important tool in medicinal chemistry and drug discovery. Additionally, the boronic ester functionality allows for further functionalization and diversification of the molecule, making it a versatile building block for the synthesis of complex organic compounds.

Upstream product

• 866546-07-8 5-chloro-1H-pyrrolo[2,3-b]pyridine 
• 866546-10-3 3-bromo-5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine 
• 73183-34-3 bis(pinacol)diborane 
• 98-59-9 p-toluenesulfonyl chloride 
• 866546-09-0 3-bromo-5-chloro-1 H-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 

Downstream Products

• 1346172-89-1 methyl 6-{5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-pyrazine-2-carboxylate 
• 1363407-75-3 potassium (5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)trifluoroborate 
• 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 
• 1346172-93-7 diethyl (6-{5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-pyrazin-2-yl)propanedioate 
• 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 
• 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 
• 1346172-78-8 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 
• 1259012-01-5 5-chloro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine 
• 1259009-30-7 tert-butyl (3S)-3-[[2-[5-chloro-1-(p-tolylsulfonyl)pyrrolo[5,4-b]pyridin-3-yl]-5-fluoropyrimidin-4-yl]amino]piperidine-1-carboxylate 
• 1259277-58-1 (1S,2S)-N₁-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-yl)cyclohexane-1,2-diamine 

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.

Discovery of Novel, Orally Bioavailable β-Amino Acid Azaindole Inhibitors of Influenza PB2

In our efforts to develop novel small-molecule inhibitors for the treatment of influenza, we utilized molecular modeling and the X-ray crystal structure of the PB2 subunit of the influenza polymerase to optimize a series of acyclic β-amino acid inhibitors, highlighted by compound 4. Compound 4 showed good oral exposure in both rat and mouse. More importantly, it showed strong potency versus multiple influenza-A strains, including pandemic 2009 H1N1 and avian H5N1 strains and showed a strong efficacy profile in a mouse influenza model even when treatment was initiated 48 h after infection. Compound 4 offers good oral bioavailability with great potential for the treatment of both pandemic and seasonal influenza.

Discovery of a novel, first-in-class, orally bioavailable azaindole inhibitor (VX-787) of influenza PB2

In our effort to develop agents for the treatment of influenza, a phenotypic screening approach utilizing a cell protection assay identified a series of azaindole based inhibitors of the cap-snatching function of the PB2 subunit of the influenza A viral polymerase complex. Using a bDNA viral replication assay (Wagaman, P. C., Leong, M. A., and Simmen, K. A. Development of a novel influenza A antiviral assay. J. Virol. Methods 2002, 105, 105-114) in cells as a direct measure of antiviral activity, we discovered a set of cyclohexyl carboxylic acid analogues, highlighted by VX-787 (2). Compound 2 shows strong potency versus multiple influenza A strains, including pandemic 2009 H1N1 and avian H5N1 flu strains, and shows an efficacy profile in a mouse influenza model even when treatment was administered 48 h after infection. Compound 2 represents a first-in-class, orally bioavailable, novel compound that offers potential for the treatment of both pandemic and seasonal influenza and has a distinct advantage over the current standard of care treatments including potency, efficacy, and extended treatment window.