5782-12-7

Basic information

• Product Name: 2,3-bis(2-methoxyphenyl)-1H-indole
• Synonyms: 2,3-bis(2-methoxyphenyl)-1H-indole
• CAS NO: 5782-12-7
• Molecular Weight: 329.398
• Mol File: 5782-12-7.mol

Chemical Properties

• CAS DataBase Reference: 2,3-bis(2-methoxyphenyl)-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-bis(2-methoxyphenyl)-1H-indole(5782-12-7)
• EPA Substance Registry System: 2,3-bis(2-methoxyphenyl)-1H-indole(5782-12-7)

Safety Data

• Hazardous Substances Data: 5782-12-7(Hazardous Substances Data)

Upstream product

• 98-95-3 nitrobenzene 
• 32954-65-7 N,O-diacetylphenylhydroxylamine 
• 615-43-0 2-iodophenylamine 
• 103529-16-4 2-[(trimethylsilyl)ethynyl]aniline 
• 52670-38-9 2-ethynylaniline 
• 529-28-2 4-iodoanisol 
• 143360-93-4 N-(2-ethynylphenyl)-2,2,2-trifluoroacetamide 

Relevant articles and documents

Rhodium-Catalyzed Annulation of N-Acetoxyacetanilide with Substituted Alkynes: Conversion of Nitroarenes to Substituted Indoles

A general and efficient rhodium-catalyzed redox-neutral annulation of N-acetoxyacetanilides, readily accessible from nitroarenes, with alkynes has been accomplished for the synthesis of substituted indole derivatives. A wide range of substituted 2,3-diarylindoles were achieved from various substituted N-acetoxyacetanilides and symmetrical/unsymmetrical alkynes in good to excellent yields. The developed method was successfully integrated with the synthesis of N-acetoxyacetanilides for the efficient one-pot synthesis of indoles from nitroarenes. The important features are the introduction of N-acetoxyacetamide as a new directing group, redox-neutral annulation, an additive-free approach, wide functional group tolerance, an intramolecular version, and a one-pot reaction of nitroarenes. The method was further extended to the synthesis of potent higher analogues of indole, viz., pyrrolo[3,2-f]indoles and dibenzo[a,c]carbazoles. In addition, a plausible mechanism was proposed based on the isolation and stoichiometric study of a potential aryl-Rh intermediate.

Sequential Sonogashira/intramolecular aminopalladation/cross-coupling ofortho-ethynyl-anilines catalyzed by a single palladium source: rapid access to 2,3-diarylindoles

We have developed a practical and efficient one-pot protocol for the synthesis of 2,3-diarylindolesviaPd-catalyzed bis-arylative cyclization of variouso-ethynylanilines with aryl iodides. Mechanism studies showed that a Pd-catalyzed Sonogashira reaction took place firstly, giving an internal alkyne intermediate, which subsequently underwent intramolecular aminopalladation/cross-coupling to give access to 2,3-diarylindoles. The present methodology exhibits a broad substrate scope, producing various 2,3-diaryl indoles bearing two different aryl groups.