66354-87-8

Usage

Uses

Used in Organic Synthesis:
6-methyl-2-phenyl-1H-indole is used as a building block for the synthesis of various organic compounds, leveraging its unique molecular structure to create a range of different chemical entities.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 6-methyl-2-phenyl-1H-indole is used as a key component in the development of new therapeutic drugs, capitalizing on its potential pharmacological properties.
Used in Central Nervous System Research:
6-methyl-2-phenyl-1H-indole is utilized in research pertaining to the central nervous system, exploring its role and potential applications in this critical area of medicine.
Used as an Antiproliferative Agent:
6-methyl-2-phenyl-1H-indole is also studied for its potential as an antiproliferative agent, which could have significant implications for the treatment of various diseases characterized by uncontrolled cell growth.
Used in Pharmaceutical Development:
6-methyl-2-phenyl-1H-indole serves as a precursor in the synthesis of pharmaceuticals, contributing to the development of novel drugs with diverse therapeutic applications.
Used in Precursor Chemistry:
As a precursor in chemical reactions, 6-methyl-2-phenyl-1H-indole enables the production of a variety of organic compounds, expanding the scope of synthetic chemistry and its applications.

InChI:InChI=1/C15H13N/c1-11-7-8-13-10-15(16-14(13)9-11)12-5-3-2-4-6-12/h2-10,16H,1H3

Upstream product

• 70-11-1 α-bromoacetophenone 
• 108-44-1 1-amino-3-methylbenzene 
• 1037492-69-5 4-methyl-2-nitro-1-(2-phenylethynyl)benzene 
• 1054566-90-3 2-azido-4-methyl-1-((E)-styryl)benzene 
• 1037493-10-9 5-methyl-2-(phenylethynyl)aniline 
• 13194-69-9 2-iodo-5-methylaniline 
• 536-74-3 phenylacetylene 
• 930-30-3 cyclopent-2-enone 
• 1449516-96-4 C₁₆H₁₃BrN₂ 
• 99584-29-9 1-(3-methylphenyl)-1H-1,2,3,4-tetrazole 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 536-89-0 m-tolylhydrazine 
• 532-27-4 1-chloroacetophenone 
• 351890-68-1 2-[(3-methylphenyl)amino]-1-phenylethan-1-one 

Downstream Products

• 54880-04-5 11-methyl-9H-dibenzo[a,c]carbazole 
• 132554-36-0 1,6-dimethyl-2-phenyl-1H-indole 

Relevant academic research and scientific papers

Acid-catalyzed cleavage of C-C bonds enables atropaldehyde acetals as masked C2 electrophiles for organic synthesis

Acid-catalyzed tandem reactions of atropaldehyde acetals were established for the synthesis of three important molecules, 2,2-disubstituted indolin-3-ones, naphthofurans and stilbenes. The synthesis was realized using novel reaction cascades, which involved the same two initial steps: (i) SN2′ substitution, in which the atropaldehyde acted as an electrophile; and (ii) oxidative cleavage of the carbon-carbon bond of the generated phenylacetaldehyde-type products. Compared with literature methods, the present protocol not only avoided the use of expensive noble metal catalysts, but also enabled a simple operation.

Iron-catalysed radical cyclization to synthesize germanium-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and indolin-2-ones

A simple and efficient strategy for iron-catalysed cascade radical cyclization was developed, by which an array of germanium-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and indolin-2-ones were obtained in one pot with germanium hydrides as radical precursors. A rapid intramolecular radical trapping mode enabled the selective arylgermylation of alkenes over the prevalent hydrogermylation reaction.

Synthesis of Indoles by Reductive Cyclization of Nitro Compounds Using Formate Esters as CO Surrogates

Alkyl and aryl formate esters were evaluated as CO sources in the Pd- and Pd/Ru-catalyzed reductive cyclization of 2-nitrostyrenes to give indoles. Whereas the use of alkyl formates requires the presence of a ruthenium catalyst such as Ru3(CO)12, the reaction with phenyl formate can be performed by using a Pd/phenanthroline complex alone. Phenyl formate was found to be the most effective CO source and the desired products were obtained in excellent yields, often higher than those previously reported using pressurized CO. The reaction tolerates many functional groups, including sensitive ones like a free aldehydic group or a pendant pyrrole. Detailed experiments and kinetic studies allow to conclude that the activation of phenyl formate is base-catalyzed and that the metal doesn't play a role in the decarbonylation step. The reactions can be performed in a single thick-walled glass tube with as little as 0.2 mol-% palladium catalyst and even on a 2 g scale. The same protocol can be extended to other nitro compounds, affording different heterocycles.

Regioselective mercury(I)/palladium(II)-catalyzed single-step approach for the synthesis of imines and 2-substituted indoles

An efficient synthesis of ketimines was achieved through a regioselective Hg(I)-catalyzed hydroamination of terminal acetylenes in the presence of anilines. The Pd(II)-catalyzed cycliza-tion of these imines into the 2-substituted indoles was satisfactorily carried out by a C-H acti-vation. In a single-step approach, a variety of 2-substituted indoles were also generated via a Hg(I)/Pd(II)-catalyzed, one-pot, two-step process, starting from anilines and terminal acetylenes. The arylacetylenes proved to be more effective than the alkyl derivatives.

Modular counter-Fischer?indole synthesis through radical-enolate coupling

A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.

Focused structure-activity relationship profiling around the 2-phenylindole scaffold of a cannabinoid type-1 receptor agonist-positive allosteric modulator: site-III aromatic-ring congeners with enhanced activity and solubility

Specific tuning of cannabinoid 1 receptor (CB1R) activity by small-molecule allosteric modulators is a therapeutic modality with multiple properties inherently advantageous to therapeutic applications. We previously generated a library of unique CB1R posi

Preparation method of indole compound

The invention discloses a preparation method of a novel efficient indole compound, which comprises the following steps: by using o-nitroalkylbenzene containing various substituents as a raw material,controlling the reaction temperature to be 70-160 DEG C in an organic solution under the protection of inert gas and the participation of inorganic base, thereby obtaining the indole compound; preparing the novel indole compound containing various substituent groups through a hydrocarbon activation reaction catalyzed by a metal rhodium catalyst. The synthetic method is not reported in literature,the raw materials are easy to synthesize, no reducing agent needs to be added additionally, the method is simple in step, the indole compound containing various substituent groups does not need to beconstructed in one step through a nitroso intermediate, and the yield is high; The method is simple in unit operation, low in equipment requirement and suitable for rapidly synthesizing the indole compounds containing various substituent groups.

Room-Temperature Palladium(II)-Catalyzed Direct 2-Arylation of Indoles with Tetraarylstannanes

A palladium(II)-catalyzed direct 2-arylation of indoles by tetraarylstannanes with oxygen (balloon) as the oxidant at room temperature has been developed. Various tetraarylstannanes can be employed as aryl sources for 2-arylation of indoles in up to 89% yield, providing a practical and efficient catalytic protocol for accessing 2-arylindoles.

α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles

Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate α-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by [Ir(cod)Cl]2 (4 mol %) to provide 2-substituted indoles (up to 70% yield) in just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride and dimethylsulfoxonium methylide (23 new examples in 45-85% yield) or by imino group formation from the corresponding β-keto sulfoxonium ylides and anilines in the presence of TiCl4 as a Lewis acid (9 examples in 33-94% yield).

Pd-Catalyzed Reductive Cyclization of Nitroarenes with CO2 as the CO Source

A reductive amination process that constructs indoles, carbazoles or benzimidazoles from nitroarenes – irrespective of their electronic or steric nature – was developed that uses CO2 as the source of CO. The process is robust, tolerating common gaseous components of flue gas (H2S, SO2, NO and H2O) without adversely affecting the reductive cyclization.