317802-33-8

Usage

Structure

A derivative of indole with a methoxy group at the 5-position, an iodo substituent at the 3-position, and a sulfonyl group attached to the nitrogen atom.

Potential applications

Medicinal chemistry, pharmaceutical research, as a building block for the synthesis of new drug candidates, as a molecular probe for studying biological processes, and industrial uses in the production of specialty chemicals.

Upstream product

• 85092-86-0 3-iodo-5-methoxy-1H-indole 
• 98-59-9 p-toluenesulfonyl chloride 
• 1006-94-6 5-methoxylindole 

Downstream Products

• 1027787-24-1 5-methoxy-3-(2-methoxy-naphthalen-6-yl)-1-tosyl-1H-indole 
• 1027787-52-5 C₂₃H₂₁NO₄S 
• 1185427-08-0 C₂₂H₂₆BNO₅S 
• 1432521-43-1 2-(5-methoxy-1-tosyl-1H-indol-3-yl)benzaldehyde 
• 1432521-30-6 3-(2-(2,2-dibromovinyl)phenyl)-5-methoxy-1-tosyl-1H-indole 

Relevant academic research and scientific papers

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.

H-bonding vs Protonation of Alkynes in Regioselective Hydroamination Reactions: A Glimpse into the Reactivity of Arylogous Ynolethers and Ynamines

In this paper is described the competition and transition between hydrogen bonding and protonation of alkynes connected, on one side, to various aromatic rings and to chiral amino ester appendages on the other side. While the first mode of activation indu

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.

One-pot synthesis of camalexins and 3,3′-biindoles by the Masuda borylation-Suzuki arylation (MBSA) sequence

The Masuda borylation/Suzuki arylation (MBSA) sequence starting from N-protected 3-iodoindoles has successfully been extended to the coupling of five-membered heterocycles and indoles in the arylation step, which could not be achieved with previously developed MBSA methods. By this approach the one-pot nature of the method as well as the use of a simple catalyst system has been retained. The applicability of the method has been demonstrated by the facile synthesis of camalexins and 3,3′-biindoles, compounds of special interest due to their pronounced antifungal, antimicrobial and cytotoxic activities. The Masuda borylation/Suzuki arylation sequence furnishes in a concise one-pot manner camalexins and 3,3′-biindoles, compounds that show pronounced antifungal, antimicrobial, and cytotoxic activities. Copyright

Hydroboration and Suzuki-Miyaura coupling reactions with the electronically modulated variant of an ynamine: The synthesis of (E)-β-arylenamides

The first hydroboration of an 1-alkynylamide - the electronically modulated variant of an ynamine - is described. This hydroboration in combination with a Suzuki-Miyaura cross-coupling reaction with aryl bromides or aryl iodides allows a flexible synthesis of (E)-β-arylenamides and 3-(2'-amidovinyl)indoles with high degree of molecular diversity. (C) 2000 Elsevier Science Ltd.