115666-47-2

Usage

Uses

Used in Pharmaceutical Industry:
6-Iodoindole is used as a chemical intermediate for the synthesis of linear tripeptides, which are essential components in the preparation of right-hand segments of complestatin. Complestatin is a potent anti-inflammatory and anti-fibrotic agent that has shown promise in the treatment of various diseases, including cancer and idiopathic pulmonary fibrosis. The use of 6-Iodoindole in the synthesis of these tripeptides allows for the development of more effective and targeted therapies in the pharmaceutical industry.

InChI:InChI=1/C8H6IN/c9-7-2-1-6-3-4-10-8(6)5-7/h1-5,10H

Upstream product

• 41252-97-5 4-iodo-2-nitrotoluene 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 106-49-0 p-toluidine 
• 68-12-2 N,N-dimethyl-formamide 
• 52415-29-9 6-bromo-1H-indole 
• 115666-43-8 1-acetyl-2,3-dihydro-6-iodoindole 
• 22949-08-2 1-acetyl-6-nitro-2,3-dihydroindole 
• 19727-83-4 6-nitroindoline 
• 62368-29-0 1-acetyl-6-aminoindoline 
• 115666-46-1 6-iodo-2,3-dihydro-1H-indole 

Downstream Products

• 115666-46-1 6-iodo-2,3-dihydro-1H-indole 
• 872876-52-3 (R)-N-carbobenzyloxy-6'-iodotryptophan 
• 872877-29-7 (S)-N-carbobenzyloxy-6'-iodotryptophan 
• 872876-93-2 (R)-N-carbobenzyloxy-6'-iodotryptophan tert-butyl ester 
• 872877-20-8 (R)-6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-N-carbobenzyloxytryptophan 
• 872877-18-4 (R)-6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-N-carbobenzyloxy-6'-iodotryptophan tert-butyl ester 
• 872876-83-0 (R,R)-(6'-iodo-N-carbobenzyloxytryptophyl)-3',5'-dichloro-4'-hydroxyphenylglycine tert-butyl ester 
• 872876-95-4 (R,R)-3-{6-[3-(N-tert-butoxycarbonyl-2-methoxycarbonylmethylamino)-5-iodo-6-methoxyphenyl]indol-3-yl}-2-carbobenzyloxyaminopropionic acid tert-butyl ester 
• 1217335-95-9 6-iodo-1-tosyl-1H-indole 
• 1260152-98-4 1-(1H-indol-6-yl)-3-phenylpropyl 4-(trifluoromethyl)benzoate 
• 1429922-13-3 ethyl 5-(6-iodoindolin-1-yl)pentanoate 
• 1429922-27-9 C₂₈H₃₀N₈O₃ 
• 1429922-28-0 C₂₈H₃₀N₈O₃ 
• 1429922-29-1 C₃₁H₃₅N₅O₅ 

Relevant academic research and scientific papers

Rapid and efficient copper-catalyzed finkelstein reaction of (hetero)aromatics under continuous-flow conditions

A general, rapid, and efficient method for the copper-catalyzed Finkelstein reaction of (hetero)aromatics has been developed using continuous flow to generate a variety of aryl iodides. The described method can tolerate a broad spectrum of functional groups, including N-H and O-H groups. Additionally, in lieu of isolation, the aryl iodide solutions were used in two distinct multistep continuous-flow processes (amidation and Mg-I exchange/nucleophilic addition) to demonstrate the flexibility of this method.

SmI2-mediated dimerization of indolylbutenones and synthesis of the myxobacterial natural product indiacen B

The synthesis and reactivity of indole derivatives substituted in the benzene section was studied. Starting materials 4- and 6-iodo-indole were conveniently prepared via the Batcho-Leimgruber route and purified by sublimation. Novel vicinally indolyl-subs

Monoamine Oxidase (MAO-N) Biocatalyzed Synthesis of Indoles from Indolines Prepared via Photocatalytic Cyclization/Arylative Dearomatization

The biocatalytic aromatization of indolines into indole derivatives exploiting monoamine oxidase (MAO-N) enzymes is presented. Indoline substrates were prepared via photocatalytic cyclization of arylaniline precursors or via arylative dearomatization of unsubstituted indoles and in turn chemoselectively aromatized by the MAO-N D11 whole cell biocatalyst. Computational docking studies of the indoline substrates in the MAO-N D11 catalytic site allowed for the rationalization of the biocatalytic mechanism and experimental results of the biotransformation. This methodology represents an efficient example of biocatalytic synthesis of indole derivatives and offers a facile approach to access these aromatic heterocycles under mild reaction conditions.

Diastereoselective Total Synthesis of Raputindole A

The first diastereoselective total synthesis of the bisindole alkaloid raputindole A is reported. After Au(I)-catalyzed assembly of the cyclopenta[f]indole tricycle, it was possible to hydrogenate the indene double bond regio- A nd diastereoselectively through iridium catalysis, guided by a preinstalled hydroxy function. Attempted HWE reaction led to formal elimination of formaldehyde from an α-quaternary cyclopentane carbaldehyde, which was circumvented by Takai olefination. After Suzuki-Miyaura cross coupling and deprotection/oxidation, (±)-raputindole A was obtained in 13 linear steps in 18% overall yield.

Total Synthesis and Absolute Configuration of Raputindole A

The first total synthesis of the bisindole alkaloid raputindole A from the rutaceous plant Raputia simulans is reported. The key step is a Au(I)-catalyzed cyclization that assembles the cyclopenta[f]indole tricycle from a 6-alkynylated indoline precursor. The isobutenyl side chain was installed by Suzuki-Miyaura cross-coupling, followed by a regioselective reduction employing LiDBB. Starting from 6-iodoindole, the sequence needs nine steps and provided (±)-raputindole A in 6.6% overall yield. The absolute configuration of the natural product (+)-raputindole A was determined by quantum chemical calculation of the ECD spectrum.

A Bifunctional Fluorogenic Rhodamine Probe for Proximity-Induced Bioorthogonal Chemistry

Bioorthogonal reactions have emerged as a versatile tool in life sciences. The inverse electron demand Diels–Alder reaction (DAinv) stands out due to the availability of reactants with very fast kinetics. However, highly reactive dienophiles suffer the disadvantage of being less stable and prone to side reactions. Herein, we evaluate the extent of acceleration of rather unreactive but highly stable dienophiles by DNA-templated proximity. To this end, we developed a modular synthetic route for a novel bifunctional fluorogenic tetrazine rhodamine probe that we used to determine the reaction kinetics of various dienophiles in a fluorescence assay. Under proximity-driven conditions the reaction was found to be several orders of magnitude faster, and we observed almost no background reaction when proximity was not induced. This fundamental study identifies a minimally sized fluorogenic tetrazine dienophile reactant pair that has potential to be generally used for the visualization of biomolecular interactions with temporal and spatial resolution in living systems.

EGFR INHIBITOR, AND PREPARATION AND APPLICATION THEREOF

A 4-substituted-2-(N-(5-substituted allyl amide)phenyl)amino)pyrimidine derivative as represented by formula (I), and a preparation and application thereof as an EGFR inhibitor. The compound has activity of inhibiting the L858R EGFR mutant, the T790M EGFR mutant and the exon 19 deletion activating mutant, may be used to treat diseases mediated alone or in part by EGFR mutant activity, and has a wide application in drugs preventing and treating cancers, particularly non-small cell lung cancer.

Synthesis of photoactivatable azido-acyl caged oxazine fluorophores for live-cell imaging

We report the design and synthesis of a photoactivatable azido-acyl oxazine fluorophore. Photoactivation is achieved cleanly and rapidly with UV light, producing a single fluorescent oxazine photoproduct. We demonstrate the utility of azido-acyl caged oxazines for protein specific labeling in living mammalian cells using the TMP-tag technology.

Ligand-enabled β-C-H arylation of α-amino acids using a simple and practical auxiliary

Pd-catalyzed β-C-H functionalizations of carboxylic acid derivatives using an auxiliary as a directing group have been extensively explored in the past decade. In comparison to the most widely used auxiliaries in asymmetric synthesis, the simplicity and practicality of the auxiliaries developed for C-H activation remains to be improved. We previously developed a simple N-methoxyamide auxiliary to direct β-C-H activation, albeit this system was not compatible with carboxylic acids containing α-hydrogen atoms. Herein we report the development of a pyridine-type ligand that overcomes this limitation of the N-methoxyamide auxiliary, leading to a significant improvement of β-arylation of carboxylic acid derivatives, especially α-amino acids. The arylation using this practical auxiliary is applied to the gram-scale syntheses of unnatural amino acids, bioactive molecules, and chiral bis(oxazoline) ligands.

LIGAND-CONTROLLED C(SP3)-H ARYLATION AND OLEFINATION IN SYNTHESIS OF UNNATURAL CHIRAL ALPHA AMINO ACIDS

The use of ligands to tune the reactivity and selectivity of transition metal-catalysts for C(-sp3)-H bond functionalization is a central challenge in synthetic organic chemistry. Herein, we report a rare example of catalyst-controlled C(sp3)-H arylation using pyridine and quinoline derivatives: the former promotes exclusive monoarylation, whereas the latter activates the catalyst further to achieve diarylation. Successive application of these ligands enables the sequential diarylation of a methyl group in an alanine derivative with two different aryl iodides, affording a wide range of β-Ar-p-Ar ' -cc-amino acids with excellent levels of diastereoselectivity (d.r. > 20:1). Both configurations of the β-chiral center can be accessed by choosing the order in which the aryl groups are installed. The use of a quinoline derivative as a ligand also enables C(sp3)-H olefination of a protected alanine.