5782-14-9

Basic information

• Product Name: 1H-Indole, 3-(4-methoxyphenyl)-2-methyl-
• CAS NO: 5782-14-9
• Molecular Formula: C16H15NO
• Molecular Weight: 237.301
• Mol File: 5782-14-9.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 1H-Indole, 3-(4-methoxyphenyl)-2-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole, 3-(4-methoxyphenyl)-2-methyl-(5782-14-9)
• EPA Substance Registry System: 1H-Indole, 3-(4-methoxyphenyl)-2-methyl-(5782-14-9)

Safety Data

• Hazardous Substances Data: 5782-14-9(Hazardous Substances Data)

Usage

General Description

1H-Indole, 3-(4-methoxyphenyl)-2-methyl- is a chemical compound with the molecular formula C17H15NO. It is a derivative of the heterocyclic compound indole, containing a 4-methoxyphenyl and 2-methyl substituent. This chemical is commonly used in organic synthesis and medicinal chemistry, with potential applications in pharmaceuticals and agrochemicals. It has been studied for its biological activities, including its potential as an anticancer agent and as a ligand for various receptors. Additionally, it has been investigated for its role as a precursor in the synthesis of various natural and synthetic compounds.

Upstream product

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• 201230-82-2 carbon monoxide 
• 199168-43-9 4-(4-methoxy-phenyl)-3-methyl-cinnoline 
• 577-19-5 2-nitrophenyl bromide 
• 424811-46-1 N'-(1-(4-methoxyphenyl)propylidene)-4-methylbenzenesulfonohydrazide 
• 183171-83-7 1-(4-methoxyphenyl)-1-phenyl-2-propanone 

Relevant articles and documents

A palladium-catalyzed Barluenga cross-coupling – Reductive cyclization sequence to substituted indoles

A short and flexible synthesis of substituted indoles employing two palladium-catalyzed reactions, a Barluenga cross-coupling of p-tosylhydrazones with 2-nitroarylhalides followed by a palladium–catalyzed, carbon monoxide–mediated reductive cyclization has been developed. A one-pot, two-step methodology was further developed, eliminating isolation and purification of the cross-coupling product. This was accomplished by utilizing the initially added 0.025 equivalents of bis(triphenylphosphine)palladium dichloride, thus serving a dual role in the cross-coupling and the reductive cyclization. It was found that addition of 1,3-bis(diphenylphosphino)propane and carbon monoxide after completion of the Barluenga reaction afforded, in most cases, significantly better overall yields.

FeCl3 catalyzed intermolecular reaction between enol ethers and anilines: Access to 2,3-substituted indoles through aryl group migration

An intermolecular FeCl3 catalyzed reaction between anilines and enol ethers is described. A variety of enol ethers and aromatic amines undergo a C[sbnd]C bond formation followed by cyclization via C[sbnd]N bond formation to afford the 2,3-disubstituted indoles, involving an unexpected aryl group migration. In this methodology, anilines act as bis-nucleophiles, wherein the initial attack occurs at the α-position of enol ether from the ortho position of aniline followed by the subsequent reaction of the amine moiety of aniline at the β-position, leading to the indole framework. This method is simple, obviates the use of expensive/hazardous transition-metal catalysts, and offers a wide range of substrate scope.

Pd-catalyzed C–H bond activation of Indoles for Suzuki reaction

Abstract: We present a practical method for Suzuki coupling by which unprotected or N-protected indoles may be selectively arylated in the C2-position through direct C–H bond activation by electrophilic Pd(TFA) 2 catalyst. The protocol is operationally simple as it is carried out in dioxane/water mixture, and air as the sole oxidant at room temperature. Various 2-arylated indoles were obtained in good yields. The protocol works for benzofuran, pyrrole and thiophene also. Graphic abstract: Selective C-2 arylation of heterocycles using Pd(II) catalyst via C–H activation was performed under ambient condition. C3–C2 migration of organopalladium intermediate controls the reaction pathway.[Figure not available: see fulltext.].