5784-95-2

Usage

Uses

Used in Pharmaceutical Research:
2-(4-methoxyphenyl)-1H-indole is used as a research compound for studying the effects of psychoactive substances on the 5-HT2A receptor. Its agonistic action at this receptor makes it a valuable tool for understanding the mechanisms of hallucinogenic drugs and their potential therapeutic applications.
Used in Drug Development:
In the pharmaceutical industry, 2-(4-methoxyphenyl)-1H-indole is used as a lead compound for the development of new drugs targeting the 5-HT2A receptor. Its potent agonistic activity and unique chemical structure provide a foundation for designing and optimizing novel therapeutic agents with potential applications in various psychiatric and neurological disorders.
Used in Forensic Toxicology:
2-(4-methoxyphenyl)-1H-indole is used as a reference substance in forensic toxicology for the identification and analysis of novel psychoactive substances. Its presence in biological samples can be detected and quantified using various analytical techniques, aiding in the investigation of drug-related incidents and the enforcement of drug control regulations.

InChI:InChI=1/C15H13NO/c1-17-13-8-6-11(7-9-13)15-10-12-4-2-3-5-14(12)16-15/h2-10,16H,1H3

Upstream product

• 33630-06-7 N-(4-methoxybenzylidene)-2-methylbenzenamine 
• 6832-17-3 2-diazo-1-(4-methoxyphenyl)ethanone 
• 62-53-3 aniline 
• 24310-46-1 4-methoxyacetophenone phenylhydrazone 
• 120-72-9 indole 
• 696-62-8 para-iodoanisole 
• 143321-89-5 2,2,2-trifluoro-N-(2-iodophenyl)acetamide 
• 768-60-5 4-methoxyphenylacetylen 
• 869278-16-0 2-(2-(4-methoxyphenyl)-1H-indol-1-yl)acetic acid 
• 917-54-4 methyllithium 
• 88-72-2 1-methyl-2-nitrobenzene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 121387-01-7 1-(4-methoxyphenyl)-2-(2-nitrophenyl)acetylene 
• 4248-19-5 tert-butyl carbazate 

Downstream Products

• 77587-84-9 2-{(4,5-Dihydro-1H-imidazol-2-yl)-[2-(4-methoxy-phenyl)-1H-indol-3-ylmethyl]-amino}-ethanol; hydriodide 
• 77587-85-0 3-{(4,5-Dihydro-1H-imidazol-2-yl)-[2-(4-methoxy-phenyl)-1H-indol-3-ylmethyl]-amino}-propan-1-ol; hydriodide 
• 77587-86-1 1-{(4,5-Dihydro-1H-imidazol-2-yl)-[2-(4-methoxy-phenyl)-1H-indol-3-ylmethyl]-amino}-butan-1-ol; hydriodide 
• 130283-93-1 methyl (E)-3-<2'-(4''-methoxyphenyl)-1'H-indole-3'-yl>prop-2-enoate 
• 54888-60-7 2-(4-methoxyphenyl)-2,3-dihydro-1H-indole 
• 869278-12-6 [2-(4-methoxy-phenyl)-indol-1-yl]-acetic acid ethyl ester 
• 1224200-06-9 3-methoxy-5,6-diphenylindolo[2,1-a]isoquinoline 
• 1298069-16-5 2-(4-methoxyphenyl)-3-((triisopropylsilyl)ethynyl)-1H-indole 
• 1351939-84-8 2-amino-4-(2-(4-methoxyphenyl)-1H-indol-3-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 
• 1351939-86-0 2-amino-4-(2-(4-methoxyphenyl)-1H-indol-3-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 
• 111500-91-5 3-hydroxy-3-(4-methoxyphenyl)-1,3-dihydro-2H-indol-2-one 

Relevant academic research and scientific papers

Application of polymer-bound phosphonium salts as traceless supports for solid phase synthesis

The utility of the phosphonium group as a traceless linker for the solid phase synthesis of small organic molecules is demonstrated by the elaboration of polymer-bound phosphonium salts and their subsequent cleavage to alkyl, alkenyl and heteroaryl produc

Iminyl-radicals by electrochemical decarboxylation of α-imino-oxy acids: construction of indole-fused polycyclics

Iminyl radicals are reactive intermediates that can be used for the construction of various valuable heterocycles. Herein, the electrochemical decarboxylation of α-imino-oxy acids for the generation of iminyl radicals has been accomplished under exogenous-oxidant- and metal-free conditions through the use ofnBu4NBr as a mediator. The resulting iminyl radicals undergo intramolecular cyclization smoothly with the adjacent (hetero)arenes to afford a series of indole-fused polycyclic compounds.

Copper-Catalyzed Enantioselective C-H Arylation between 2-Arylindoles and Hypervalent Iodine Reagents

The copper-catalyzed enantioselective C-H arylation between 2-arylindoles and hypervalent iodine reagents has been successfully developed, which provides a convenient and economical route to the highly atroposelective synthesis of axially chiral indole de

N-Hydroxyphthalimidyl diazoacetate (NHPI-DA): A modular methylene linchpin for the C-H alkylation of indoles

Despite the extensive studies on the reactions between conventional diazocompounds and indoles, these are still limited by the independent synthesis of the carbene precursors, the specific catalysts, and the required multi-step manipulation of the products. In this work, we explore redox-Active carbenes in the expedited and divergent synthesis of functionalized indoles. NHPI-DA displays unusual efficiency and selectivity to yield insertion products that can be swiftly elaborated into boron and carbon substituents that are particularly problematic in carbene-mediated reactions.

B(C6F5)3-Catalyzed Electron Donor-Acceptor Complex-Mediated Aerobic Sulfenylation of Indoles under Visible-Light Conditions

An efficient B(C6F5)3-catalyzed aerobic oxidative C-S cross-coupling reaction of thiophenol with indoles was developed, affording a wide range of diaryl sulfides in good yields. An electron donor-acceptor complex between B(C6F5)3 and indoles was formed, facilitating the photoinduced single-electron transfer (SET) from indole substrates to the B(C6F5)3 catalyst. This protocol demonstrates a new reaction model using B(C6F5)3 as a single-electron oxidant.

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.

An iron(iii)-catalyzed dehydrogenative cross-coupling reaction of indoles with benzylamines to prepare 3-aminoindole derivatives

We report a green cascade approach to prepare a variety of 3-aminoindole derivatives in good to excellent yields through an iron(iii)-catalyzed dehydrogenative cross-coupling reaction of 2-arylindoles and primary benzylamines under mild reaction conditions. Mechanistic studies show that a cascade reaction involves a tert-butyl nitrite (TBN)-mediated nitrosation of 2-substituted indoles and a 1,5-hydrogen shift to afford indolenine oximes, sequential iron(iii)-catalyzed condensation and a 1,5-hydrogen shift over four steps in a one-pot reaction. The reaction shows a broad substrate scope of indoles and benzylamines and tolerates a wide range of functional groups. Moreover, the reaction is easily performed at the gram scale without producing waste after the reaction is completed. The 3-aminoindole product is purified by simple extraction, washing, and recrystallization without flash column chromatography. A double imine ligand containing the 3-aminoindole unit is facile to obtain in a 52% yield in one step. The present method highlights readily available starting materials, a simple purification procedure, and the usage of cheap, nontoxic, and environmentally benign iron(iii) catalysts. This journal is

Synthesis of Substituted Anilines from Cyclohexanones Using Pd/C-Ethylene System and Its Application to Indole Synthesis

The synthesis of anilines and indoles from cyclohexanones using a Pd/C-ethylene system is reported. A simple combination of NH4OAc and K2CO3 under nonaerobic conditions was found to be the most suitable to perform this reaction. Hydrogen transfer between cyclohexanone and ethylene generates the desired products. The reaction tolerates a variety of substitutions on the starting cyclohexanones.

Pd/β-cyclodextrin-catalyzed C-H functionalization in water: A greener approach to regioselective arylation of (NH)-indoles with aryl bromides

A greener and more practical strategy for the site-selective C-H arylation of (NH)-indoles via coupling of (hetero)aryl bromides was developed, in which β-cyclodextrin, acting as both a ligand for Na2PdCl4 and a host for indoles, enables the reactions to occur easily in water. The key advantage of this method is the ingenious merging of aqueous homogeneous catalysis and ligand mediation, leading to the highly regioselective formation of C3-arylindoles with a broad substrate scope and functional-group tolerance. Moreover, the regioselectivity can be switched from the C3 to the C2-position by varying the nature of the base without recourse to employing ArI as substrates.

Method for synthesizing 2-substituted indole derivative under catalysis of copper

The invention relates to a method for synthesizing a 2-substituted indole derivative under the catalysis of copper, which comprises the following step of: reacting by taking copper acetylacetonate (Cu (acac) 2) as a catalyst and taking indole and halogenated hydrocarbon as raw materials to obtain the 2-substituted indole derivative. Compared with the prior art, the method has the advantages that the copper acetylacetonate Cu (acac) 2 which is low in price, easy to obtain and stable in property is used as the catalyst, the method is green and economical, the catalyst is used for catalyzing the indole and halogenated hydrocarbon to react to synthesize the 2-substituted indole derivative, the reaction condition is mild, and the selectivity and yield of the product are high; and the synthesis method is simple and green, the 2-substituted indole derivative is directly constructed by using cheap and easily available raw materials indole and halogenated hydrocarbon, and the 2-substituted indole derivative has good substrate universality and has wide application value in the fields of pharmaceutical chemistry, fine chemical industry and the like.