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Usage

Uses

Used in Organic Synthesis:
2-iodo-1-methyl-1H-indole is used as an intermediate in organic synthesis for the production of other organic compounds and pharmaceuticals. Its unique structure allows for versatile reactions and the creation of a wide range of molecules.
Used in Pharmaceutical Research:
In pharmaceutical research, 2-iodo-1-methyl-1H-indole serves as a key intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Chemical Reactions:
2-iodo-1-methyl-1H-indole is utilized as a reagent in chemical reactions such as Suzuki coupling and Heck reactions. Its distinct chemical structure and reactivity make it a valuable component in these processes.
Used in Antimicrobial Research:
2-iodo-1-methyl-1H-indole has been studied for its potential antimicrobial properties, indicating its use in the development of new antimicrobial agents to combat resistant strains of bacteria.
Used in Anticancer Research:
Additionally, 2-iodo-1-methyl-1H-indole is being investigated for its potential anticancer properties, which could lead to its application in the development of novel cancer treatments.

Upstream product

• 603-76-9 1-methylindole 
• 26340-49-8 2-iodo-1H-indole 
• 74-88-4 methyl iodide 
• 120-72-9 indole 

Downstream Products

• 128351-01-9 1-methyl-2-(2-phenylethynyl)-1H-indole 
• 603-76-9 1-methylindole 
• 89246-30-0 2-bromo-1-methyl-1H-indole 
• 1186722-12-2 1-methyl-2-(5-(1-tosyl-1,4,5,6-tetrahydropyridin-3-yl)pent-1-ynyl)-1H-indole 
• 3558-24-5 1-methyl-2-phenyl-1H-indole 
• 185536-18-9 2-(2-cyclohexylidenevinyl)-1-methylindole 
• 23768-17-4 1-Methyl-2-(3-pyridyl)indol 
• 1038998-78-5 ethyl-2-(9-methyl-2-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)acetate 

Relevant academic research and scientific papers

Atom Efficient Magnesiation of N-Substituted Alkyl Indoles with a Mixed Sodium-Magnesium Base

This study presents the alkali metal mediated magnesiation (AMMMg) of three N-alkylated indoles with the mixed Na/Mg base [(TMEDA)Na(TMP)2Mg(CH2SiMe3)] 1 (TMEDA = N,N,N′,N′-tetramethylethylenediamine, TMP = 2,2,6,6-tetramethylpiperidine). All three magnesiated indoles have been successfully characterised by single-crystal X-ray diffraction and solution state NMR studies, whereas iodolysis and Pd-catalysed cross coupling have been investigated. The steric nature of the N-alkyl group changes the reactivity and efficiency of 1 to give either atom efficient disodium tetraindol-2-ylmagnesiates [(Na-TMEDA)2Mg(α-C9H8N)4] 2 and [(Na-TMEDA)2Mg(α-C10H11N)4] 3, or [(TMEDA)Na(TMP)(α-C11H12N)Mg(TMP)] 4, whereby only one indole molecule is selectively deprotonated.

Intermolecular Desymmetrizing Gold-Catalyzed Yne–Yne Reaction of Push–Pull Diarylalkynes

Push–pull diaryl alkynes are dimerized in the presence of a cationic gold catalyst. The polarized structure of the applied starting materials enables the generation of a highly reactive vinyl cation intermediate in an intermolecular reaction. Trapping of the vinyl cation by a nucleophilic attack of the electron-poor aryl unit then leads to the selective formation of highly substituted naphthalenes in a single step and in complete atom economy.

ARYL RECEPTOR MODULATORS AND METHODS OF MAKING AND USING THE SAME

The present invention is generally directed towards compounds capable of binding the aryl hydrocarbon receptor and modulating its activity,methods of treating inflammatory conditions such as Crohn's disease using such compounds, and pharmaceutical compositions comprising such compounds. Also provided are methods of increasing levels of IL-22 in a subject and/or decreasing levels of IFN-γ in a subject.

Stereoselective synthesis of spirocyclic oxindoles based on a one-pot Ullmann coupling/Claisen rearrangement and its application to the synthesis of a hexahydropyrrolo[2,3-b]indole alkaloid

An efficient and convenient approach to the synthesis of spirocyclic oxindoles from iodoindoles has been developed. The most striking feature of this approach is that the sequential intramolecular Ullmann coupling and Claisen rearrangement proceeds in a one-pot manner to afford 3-spiro-2-oxindoles in good yield with excellent diastereoselectivity. Application of this one-pot reaction to chiral non-racemic tertiary alcohol substrates resulted in complete chirality transfer to the spirocyclic quaternary carbon. Using this method, asymmetric total synthesis of (-)-debromoflustramine B was accomplished.

σ-alkylpalladium intermediates in intramolecular Heck reactions: Isolation and catalytic activity

The isolation of σ-alkylpalladium Heck intermediates, possible when β-hydride elimination is inhibited, is a rather rare event. Performing intramolecular Heck reactions on Nallyl-2-halobenzylamines in the presence of [Pd(PPh3)4], we isolated and characterized a series of stable bridged palladacycles containing an iodine or bromine atom on the palladium atom. Indolyl substrates were also tested for isolation of the corresponding com- plexes. X-ray crystallographic analysis of one of the indolyl derivatives revealed the presence of a five-membered palladacycle with the metal center bearing a PPh3 ligand and an iodine atom in a cis position with respect to the nitrogen atom. The stability of the σ-alkylpalladium complexes is probably a consequence of the strong constraint resulting from the bridged junction that hampers the cisoid conformation essential for β-hydride elimination. Subsequently, the thus obtained bridged five-membered palladacycles were proven to be effective precatalysts in Heck reactions as well as in cross-coupling processes such as Suzuki and Stille reactions.

Highly diastereoselective one-pot synthesis of spirocyclic oxindoles through intramolecular Ullmann coupling and Claisen rearrangement

(Chemical Equation Presented) An efficient and convenient approach to the synthesis of spirocyclic oxindoles from iodoindoles involves a sequential intramolecular C-O Ullmann coupling reaction and Claisen rearrangement (see scheme). The one-pot procedure affords 3-spiro-2-oxindoles in good yield with excellent diastereoselectivities.

A convenient synthesis of 2-nitroindoles

The reaction of 2-iodo- and 2-bromoindoles with silver nitrite in aqueous acetone affords the corresponding 2-nitroindoles in modest to good yields.

Benzannulation reactions of Fischer carbene complexes for the synthesis of indolocarbazoles

The synthesis of indolocarbazoles was achieved via photochemical and thermal annulation reactions of chromium Fischer carbene complexes. This methodology allows for facile incorporation of hydrogen bonding functionality which complements the pharmacophore contained within bioactive indolocarbazole natural products.

Synthesis of indolocarbazoles via sequential palladium catalyzed cross- coupling and benzannulation reactions

Differentially substituted indolocarbazoles are readily prepared via a synthetic route employing two palladium catalyzed reactions. First, biindoles are prepared from a palladium catalyzed cross coupling reaction. Second, a new palladium catalyzed benzannulation reaction employing biindolyl iodides and alkynes provides indolocarbazoles.