4375-15-9

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Methyl-2,3-dihydro-1H-indole is utilized as a key intermediate in the synthesis of various pharmaceuticals due to its ability to form the basis of more complex molecular structures. Its presence in the development of new drugs highlights its importance in medicinal chemistry.
Used in Organic Chemistry:
As a building block for organic compounds, 3-Methyl-2,3-dihydro-1H-indole is employed in organic chemistry for the creation of a wide array of chemical entities, contributing to the advancement of chemical research and the development of novel materials.
Used in Aromatics and Fragrance Industry:
3-Methyl-2,3-dihydro-1H-indole is used as a component in the aroma profile of certain natural products, adding to the complexity and richness of scents in essential oils and fragrance compounds. Its inclusion in these products underscores its role in enhancing the sensory experience of consumers.
Used in Research and Development:
3-Methyl-2,3-dihydro-1H-indole is employed in scientific research to explore its potential pharmacological properties, particularly its effects on the central nervous system. This research is crucial for understanding the compound's therapeutic potential and for identifying new avenues for drug discovery and development.

InChI:InChI=1/C9H11N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-5,7,10H,6H2,1H3

Upstream product

• 83-34-1 3-Methylindole 
• 19155-23-8 3-methylindoline-2-thione 
• 40800-77-9 3-methyl-3-methylthioindol-2-one 
• 73396-91-5 2-bromo-N-(prop-2-enyl)aniline 
• 115802-63-6 N-(2-bromophenyl)-N-methyl-p-toluenesulfonamide 
• 134478-84-5 (2-Bromo-phenyl)-di-prop-2-ynyl-amine 
• 76653-05-9 4-methyl-3,4-dihydro-2,1-benothiazine 2,2-oxide 
• 35774-48-2 1-azido-2-(propan-2-yl)benzene 
• 62-53-3 aniline 
• 337966-00-4 2-(ortho-bromophenyl)-2-methyl-ethylamine 
• 118670-83-0 N-(2-iodophenyl)-N-(prop-2-enyl)acetamide 
• 4165-61-1 aniline-d5 
• 1380442-07-8 N-allyl-2,3,4,5,6-pentadeuterioaniline 
• 589-09-3 N-allyl-N-phenylamine 

Downstream Products

• 83-34-1 3-Methylindole 
• 1666-13-3 diphenyl diselenide 
• 104720-96-9 3-methyl-2-(phenylselanyl)-1H-indole 
• 5257-06-7 N-(2-acetylphenyl)formamide 
• 21874-23-7 (3-methylindolin-1-yl)(phenyl)methanone 
• 210702-64-0 [(S)-3-Methyl-1-(3-methyl-2,3-dihydro-indole-1-carbonyl)-butyl]-carbamic acid benzyl ester 
• 210702-63-9 [(S)-1-Methyl-2-(3-methyl-2,3-dihydro-indol-1-yl)-2-oxo-ethyl]-carbamic acid benzyl ester 
• 37865-94-4 3-methyl-octahydro-indole 
• 643-28-7 2-isopropylaniline 
• 66624-44-0 1-chloroacetyl-3-methyl-2,3-dihydro-indole 
• 861603-80-7 benzoic acid-[2-(β-chloro-isopropyl)-anilide] 
• 1265521-40-1 1-[(4-chlorophenyl)methyl]-1H-indole-3-methane 
• 1294041-94-3 N-cyclohexyl-3-methylindoline-1-carboxamide 
• 1361029-53-9 1-(3-methyl-1H-indol-1-yl)-2-phenylprop-2-en-1-one 

Relevant academic research and scientific papers

MILD REDUCTION OF INDOLES TO INDOLINES WITH ZINC BOROHYDRIDE

Mild reduction of indoles to indolines was achieved by using zinc borohydride as a neutral reducing agent.

Palladium-Catalyzed Direct and Specific C-7 Acylation of Indolines with 1,2-Diketones

The indole scaffold is a ubiquitous and useful substructure, and extensive investigations have been conducted to construct the indole framework and/or realize indole modification. Nevertheless, the direct selective functionalization on the benzenoid core must overcome the high activity of the C-3 position and still remains highly challenging. Herein, a palladium-catalyzed direct and specific C-7 acylation of indolines in the presence of an easily removed directing group was developed. This strategy usually is considered as a practical strategy for the preparation of acylated indoles because indoline can be easily converted to indole under oxidation conditions. In particular, our strategy greatly improved the alkacylation yield of indolines for which only an unsatisfactory yield could be achieved in the previous studies. Furthermore, the reaction can be scaled up to gram level in the standard reaction conditions with a much lower palladium loading (1 mol %).

Stereospecific N-acylation of indoles and corresponding microwave mediated synthesis of pyrazinoindoles using hexafluoroisopropanol

We envisioned a facile construction of diversified pyrazinoindoles by using 1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) as the solvent and catalyst, hence eliminating metal catalyzed routes for its development. The process is facilitated by HFIP that has emerged as a powerful tool for development of novel fused heterocycles. This cascade approach blends the asymmetric N-acylation with consecutive intramolecular cyclisation via Pictet-Spengler reaction as an efficient tool forming overall two stereogenic centers. Our approach deals with incorporation of L-amino acid on substituted indoles to provide the chiral N-acylated indole precursor followed by cyclisation to access pyrazinoindole derivatives in high enantiomeric excess up to >99% in good to excellent yields, which have great potential as molecular scaffolds in drug discovery. We have also described the mechanistic course of the reaction based on density functional theory.

Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations

Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.

Hydrogenation or Dehydrogenation of N-Containing Heterocycles Catalyzed by a Single Manganese Complex

A highly chemoselective base-metal catalyzed hydrogenation and acceptorless dehydrogenation of N-heterocycles is presented. A well-defined Mn complex operates at low catalyst loading (as low as 2 mol %) and under mild reaction conditions. The described catalytic system tolerates various functional groups, and the corresponding reduced heterocycles can be obtained in high yields. Experimental studies indicate a metal-ligand cooperative catalysis mechanism.

Aerobic Dehydrogenation of N-Heterocycles with Grubbs Catalyst: Its Application to Assisted-Tandem Catalysis to Construct N-Containing Fused Heteroarenes

An aerobic dehydrogenation of nitrogen-containing heterocycles catalyzed by Grubbs catalyst is developed. The reaction is applicable to various nitrogen-containing heterocycles. The exceptionally high functional group compatibility of this method was confirmed by the oxidation of an unprotected dihydroindolactam V to indolactam V. Furthermore, by taking advantage of the oxygen-mediated structural change of the Grubbs catalyst, we integrated ring-closing metathesis and subsequent aerobic dehydrogenation to develop the novel assisted-tandem catalysis using molecular oxygen as a chemical trigger. The utility of the assisted-tandem catalysis was demonstrated by the concise synthesis of N-containing fused heteroarenes including a natural antibiotic, pyocyanine.

Transition-Metal-Free Stereospecific Oxidative Annulative Coupling of Indolines with Aziridines

Tandem C-N bond formation for the oxidative annulation of indolines with aziridines is accomplished employing the combination of DDQ and NaOCl at ambient conditions. Optically active aziridine can be coupled with high enantiomeric purity (>99% ee). The substrate scope, stereocontrol with the enantioenriched substrate, and scale-up are the important practical advantages.

SULFONYL-SUBSTITUTED BICYCLIC COMPOUND WHICH ACTS AS ROR INHIBITOR

Provided is a sulfonyl-substituted bicyclic compound (A) which acts as a RORγ inhibitor, said compound has good RORγ inhibitory activity and is expected to be used for treating diseases mediated by a RORγ receptor in mammals.

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.

Exploiting the radical reactivity of diazaphosphinanes in hydrodehalogenations and cascade cyclizations

The remarkable reducibility of diazaphosphinanes has been extensively applied in various hydrogenations, based on and yet limited by their well-known hydridic reactivity. Here we exploited their unprecedented radical reactivity to implement hydrodehalogenations and cascade cyclizations originally inaccessible by hydride transfer. These reactions feature a broad substrate scope, high efficiency and simplicity of manipulation. Mechanistic studies suggested a radical chain process in which a phosphinyl radical is generated in a catalytic cycle via hydrogen-atom transfer from diazaphosphinanes. The radical reactivity of diazaphosphinanes disclosed here differs from their well-established hydridic reactivity, and hence, opens a new avenue for diazaphosphinane applications in organic syntheses.