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Usage

Uses

Used in Pharmaceutical Research:
1-methyl-3-(phenylmethyl)-1H-indole is utilized as a key intermediate in the synthesis of various pharmaceutical compounds, leveraging its unique structural features to enhance the development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
As an indole derivative, 1-methyl-3-(phenylmethyl)-1H-indole serves as a valuable building block in organic synthesis, enabling the creation of a wide range of chemical entities with diverse properties and functions.
Used in Drug Development:
1-methyl-3-(phenylmethyl)-1H-indole is employed as a potential candidate in drug development, particularly for the exploration of its interactions with serotonin receptors and related pathways, which could lead to the discovery of novel treatments for various disorders.
Used in the Study of Serotonin Receptors and Pathways:
1-methyl-3-(phenylmethyl)-1H-indole is used as a research tool to investigate the mechanisms of action and signaling pathways associated with serotonin receptors, providing insights into the development of targeted therapies for neurological and psychiatric conditions.
Further research is essential to fully understand the pharmacological properties of 1-methyl-3-(phenylmethyl)-1H-indole and to determine its potential therapeutic uses across different medical applications.

Upstream product

• 19260-05-0 1-methylgramine methiodide 
• 59181-45-2 (2-Chloro-phenyl)-methyl-((E)-3-phenyl-allyl)-amine 
• 1011737-23-7 N-benzyl-2-ethynyl-N-methylaniline 
• 603-76-9 1-methylindole 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 536-74-3 phenylacetylene 
• 54655-08-2 N,N-dimethyl-2-(2-phenylethynyl)aniline 
• 16886-10-5 3-benzyl-1H-indole 
• 74-88-4 methyl iodide 
• 100-46-9 benzylamine 
• 19012-03-4 N-methyl-3-formylindole 
• 1589-82-8 phenylmagnesium bromide 
• 1908-67-4 (1-methyl-1H-indol-3-yl)(phenyl)methanol 

Downstream Products

• 19012-01-2 3-benzoyl-1-methylindole 
• 1592481-97-4 ((4aS,9aS)-4a-benzyl-9-methyl-3-phenyl-4,4a,9,9a-tetrahydro-1H-pyridazino[3,4-b]indol-1-yl)(phenyl)methanone 

Relevant academic research and scientific papers

Intramolecular Addition of a Dimethylamino C(sp 3)-H Bond across C-C Triple Bonds Using IrCl(DTBM-SEGPHOS)(ethylene) Catalyst: Synthesis of Indoles from 2-Alkynyl- N -methylanilines

Intramolecular addition of a C(sp 3)-H bond of the dimethylamino group across the C-C triple bond in 2-alkynyl- N, N -dimethylanilines is effectively catalyzed by a new iridium complex, IrCl(DTBM-SEGPHOS)(C 2H 4), in mesitylene at 150 °C. The intramolecular C(sp 3)-H addition is followed by double-bond isomerization to afford 3-substituted indoles in good to high yields.

Mild Friedel–Crafts Reactions inside a Hexameric Resorcinarene Capsule: C?Cl Bond Activation through Hydrogen Bonding to Bridging Water Molecules

A novel catalytic feature of a hexameric resorcinarene capsule is highlighted. The self-assembled cage was exploited to promote the Friedel–Crafts benzylation of several arenes and heteroarenes with benzyl chloride under mild conditions. Calculations showed that there are catalytically relevant hydrogen-bonding interactions between the bridging water molecules of the capsule and benzyl chloride, which is fundamental for the activation of the C?Cl bond. The capsule controls the reaction outcome. Inside the inner cavity of the capsule, N-methylpyrrole is preferentially benzylated in the unusual β-position while mesitylene reacts faster than 1,3-dimethoxybenzene despite the greater π-nucleophilicity of the latter compound.

Indole-based allosteric inhibitors of HIV-1 integrase

Employing a scaffold hopping approach, a series of allosteric HIV-1 integrase (IN) inhibitors (ALLINIs) have been synthesized based on an indole scaffold. These compounds incorporate the key elements utilized in quinoline-based ALLINIs for binding to the IN dimer interface at the principal LEDGF/p75 binding pocket. The most potent of these compounds displayed good activity in the LEDGF/p75 dependent integration assay (IC50?=?4.5?μM) and, as predicted based on the geometry of the five- versus six-membered ring, retained activity against the A128T IN mutant that confers resistance to many quinoline-based ALLINIs.

Tandem organocatalysis and photocatalysis: An anthraquinone-catalyzed indole-c3-alkylation/photooxidation/1,2-shift sequence

Quinones exhibit orthogonal ground- and excited-state reactivities and are therefore highly suitable organocatalysts for the development of sequential catalytic processes. Herein, the discovery of an anthraquinone-catalyzed thermal indole-C3-alkylation with benzylamines is described, which can be combined sequentially with a new visible-light-driven catalytic photooxidation/1,2-shift reaction. The one-flask tandem process converts indoles into 3-benzylindole intermediates, which are further transformed into new fluorescent 2,2-disubstituted indoline-3-one derivatives.

A highly efficient route to C-3 alkyl-substituted indoles via a metal-free transfer hydrogenation

A highly efficient route to C-3 alkyl-substituted indoles via completely metal-free catalytic transfer hydrogenation of 3-indolemethanols was developed. This process proceeds via vinylogous iminium intermediates formed in situ in the presence of Br?nsted

A facile access to substituted indoles utilizing palladium catalyzed annulation under microwave enhanced conditions

A facile access to differently substituted indoles using palladium catalyzed annulation reactions under microwave enhanced conditions has been achieved. A highly active and efficient catalytic system PdCl 2/(A-taphos) for the synthesis of indole via palladium catalyzed ring annulation of ortho iodo anilines and aldehydes has been developed.

General and selective C-3 alkylation of indoles with primary alcohols by a reusable Pt nanocluster catalyst

The platinum rule: Heterogeneous, additive-free C-3 selective alkylation of indoles by aliphatic and aromatic alcohols proceeded under transfer hydrogenation conditions with the reusable Pt/θ-Al2O 3 catalyst (see scheme; TON=turnover number). Copyright

Transition-Metal-Catalyzed Regioselective Alkylation of Indoles with Alcohols

The regioselective alkylation of indoles with alcohols as alkylating reagents was developed by using Pd/C or RuCl2(PPh3) 3/DPEphos {DPEphos = bis[(2-diphenylphosphanyl)phenyl] ether}as catalysts. The reaction of indole with benzyl alcohol in the presence of Pd/C and K2CO3 at 80 °C for 24 h without any solvent under in air yielded 90 % of 3-benzylindole. The corresponding 3-benzylindole was obtained in 99 % yield when the reaction was catalyzed by RuCl 2(PPh3)3/DPEphos in the presence of K 3PO4 at 165 °C for 24 h under argon. Several types of alcohols were treated with indoles under these conditions to give the corresponding 3-alkylated indoles in high yields (up to 99 %). This reaction may involve the catalyst-mediated transformation of alcohols to aldehydes, nucleophilic addition of indole to the resulting aldehydes accompanied by dehydration, and then hydrogenation. Copyright

From alcohols to indoles: A tandem Ru catalyzed hydrogen-transfer Fischer indole synthesis

In a new version of the Fischer indole synthesis, primary and secondary alcohols have been catalytically oxidized in the presence of phenylhydrazines and protic or Lewis acids to give the corresponding indoles. The overall reaction can be accomplished in one step, and the use of alcohols instead of aldehyes or ketones as starting materials has several advantages in terms of a large selection of reagents, easy handling, and safety of the process.

Rapid and general protocol towards catalyst-free friedel-crafts C-alkylation of indoles in water assisted by microwave irradiation

An efficient and simplified protocol for uncatalyzed FriedelCrafts alkylation of indoles using microwave irradiation in water is described. A series of functionalized indole derivatives has been synthesized in very short times with moderate to good yields. The combination of microwave irradiation and superheated water offers significant advantages over conventional methods, such as higher selectivities, simplicity, shorter reaction times, and no need for a catalyst.