664982-01-8

Basic information

• Product Name: 1H-Pyrrolo[2,3-b]pyridine, 3-iodo-1-[(4-Methylphenyl)sulfonyl]-
• Synonyms: 1H-Pyrrolo[2,3-b]pyridine, 3-iodo-1-[(4-Methylphenyl)sulfonyl]-;3-Iodo-1-Ttosyl-1H-pyrrolo[2,3-b]pyridine;3-iodo-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridine
• CAS NO: 664982-01-8
• Molecular Formula: C₁₄H₁₁IN₂O₂S
• Molecular Weight: 398.21881
• Mol File: 664982-01-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Pyrrolo[2,3-b]pyridine, 3-iodo-1-[(4-Methylphenyl)sulfonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrolo[2,3-b]pyridine, 3-iodo-1-[(4-Methylphenyl)sulfonyl]-(664982-01-8)
• EPA Substance Registry System: 1H-Pyrrolo[2,3-b]pyridine, 3-iodo-1-[(4-Methylphenyl)sulfonyl]-(664982-01-8)

Safety Data

• Hazardous Substances Data: 664982-01-8(Hazardous Substances Data)

Usage

Structure

Sulfonyl-substituted pyrrolopyridine derivative

Use

Commonly used in pharmaceutical research and drug development

Potential therapeutic applications

Treatment of cancer and inflammatory diseases

Investigated as

A building block in organic synthesis and medicinal chemistry

Unique features

Unique structure and pharmacological properties that make it important for further research and development in drug discovery

Kinase inhibitor potential

Demonstrated potential as a kinase inhibitor

Upstream product

• 271-63-6 7-Azaindole 
• 98-59-9 p-toluenesulfonyl chloride 
• 23616-57-1 3-iodo-1H-pyrrolo[2,3-b]pyridine 

Downstream Products

• 1432521-33-9 3-(2-(2,2-dibromovinyl)phenyl)-1-tosyl-1H-7-azaindole 
• 1432521-46-4 2-(1-tosyl-1H-7-azaindol-3-yl)benzaldehyde 
• 341998-55-8 Meriolin 1 
• 866545-91-7 1-(4-methylbenzenesulfonyl)-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine 
• 1001413-30-4 C₂₁H₁₅N₃O₂S 
• 1426083-10-4 C₂₂H₁₅N₃O₄S 
• 882562-39-2 1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-ylboronic acid 

Relevant articles and documents

Sequentially Catalyzed Three-Component Masuda-Suzuki-Sonogashira Synthesis of Fluorescent 2-Alkynyl-4-(7-azaindol-3-yl)pyrimidines: Three Palladium-Catalyzed Processes in a One-Pot Fashion

The Masuda-Suzuki-Sonogashira sequence efficiently unites, in a one-pot fashion, a borylation, an arylation, and an alkynylation in the sense of a sequentially Pd-catalyzed three-component reaction to give fluorescent 2-alkynyl-4-(7-azaindol-3-yl) pyrimid

Lead Optimization of 3,5-Disubstituted-7-Azaindoles for the Treatment of Human African Trypanosomiasis

Neglected tropical diseases such as human African trypanosomiasis (HAT) are prevalent primarily in tropical climates and among populations living in poverty. Historically, the lack of economic incentive to develop new treatments for these diseases has meant that existing therapeutics have serious shortcomings in terms of safety, efficacy, and administration, and better therapeutics are needed. We now report a series of 3,5-disubstituted-7-azaindoles identified as growth inhibitors of Trypanosoma brucei, the parasite that causes HAT, through a high-throughput screen. We describe the hit-to-lead optimization of this series and the development and preclinical investigation of 29d, a potent antitrypanosomal compound with promising pharmacokinetic (PK) parameters. This compound was ultimately not progressed beyond in vivo PK studies due to its inability to penetrate the blood-brain barrier (BBB), critical for stage 2 HAT treatments.

Novel meriolin derivatives as rapid apoptosis inducers

3-(Hetero)aryl substituted 7-azaindoles possessing multikinase inhibitor activity are readily accessed in a one-pot Masuda borylation-Suzuki coupling sequence. Several promising derivatives were identified as apoptosis inducers and, emphasizing the multik

Enantioselective Synthesis of Cyclohepta[ b]indoles via Pd-Catalyzed Cyclopropane C(sp3)-H Activation as a Key Step

An enantioselective synthesis of functionalized cyclohepta[b]indoles via Pd-catalyzed cyclopropane C-H activation followed by olefination and indole-vinylcyclopropane rearrangement is reported. The design of the chiral cyclopropane precursor was such that both enantiomeric cyclohepta[b]indoles were accessed from a single compound exhibiting a "hidden" symmetry plane. The scope of the method was demonstrated by varying the substituents on the cyclopropane as well as on the heterocycle itself.

Domino C-H functionalization reactions of gem-dibromoolefins: Synthesis of N-fused benzo[c]carbazoles

A palladium-catalyzed domino transformation of gem-dibromoolefins leading to novel polycyclic benzo[c]carbazoles is described. A unique feature of the current reaction is the participation of both bromides in C-H functionalization processes. Mechanistic studies were conducted to ascertain the sequence of reaction events, and the results indicate that the (Z)-bromide likely reacts in preference to the (E)-bromide.

A simple, two-step synthesis of 3-iodoindoles

2-Halo-anilines, protected as the corresponding sulfonamides or carbamates, can be converted very efficiently into 3-iodoindoles by sequential Sonogashira coupling with a 1-alkyne and 5-endo-dig iodocyclisation. Azaindoles can also be obtained using this methodology.