51206-91-8

Basic information

• Product Name: 3-(4-bromophenyl)-1-methyl-1H-indole
• Synonyms: 3-(4-bromophenyl)-1-methyl-1H-indole
• CAS NO: 51206-91-8
• Molecular Weight: 286.171
• Mol File: 51206-91-8.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 3-(4-bromophenyl)-1-methyl-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-bromophenyl)-1-methyl-1H-indole(51206-91-8)
• EPA Substance Registry System: 3-(4-bromophenyl)-1-methyl-1H-indole(51206-91-8)

Safety Data

• Hazardous Substances Data: 51206-91-8(Hazardous Substances Data)

Upstream product

• 615-43-0 2-iodophenylamine 
• 57056-93-6 N-methyl-2-iodoaniline 
• 59862-55-4 (E)-1-(4-bromophenyl)ethan-1-one oxime 
• 603-76-9 1-methylindole 
• 106-40-1 4-bromo-aniline 
• 120-72-9 indole 
• 1104637-53-7 B-ethynyl N-methyliminodiacetic acid boronate 
• 589-87-7 1,4-bromoiodobenzene 
• 501358-04-9 1-(4-bromophenyl)-2-(methyl(phenyl)amino)ethan-1-one 
• 98-58-8 4-bromobenzenesulfonyl chloride 
• 1038997-85-1 (4-bromophenyl)(2,4,6-triisopropylphenyl)iodonium triflate 
• 172984-02-0 N-(2-iodoanilinomethyl)succinimide 
• 172983-98-1 1-(4-Bromo-phenyl)-2-[(2-iodo-phenyl)-methyl-amino]-ethanone 
• 172983-80-1 3-(4-Bromo-phenyl)-1-methyl-2,3-dihydro-1H-indol-3-ol 

Relevant articles and documents

C3-Arylation of indoles with aryl ketonesviaC-C/C-H activations

C3-Arylation of indoles with aryl ketones is accomplishedviapalladium-catalyzed ligand-promoted Ar-C(O) cleavage and subsequent C-H arylation of indole. Various (hetero)aryl ketones are compatible in this reaction, affording the corresponding 3-arylindoles in moderate to good yields. Further introduction of an indole moiety into the natural products desoxyestrone and evodiamine demonstrate the synthetic utility of this protocol.

Au(i)/Au(iii)-Catalyzed C-N coupling

Cycling between Au(i) and Au(iii) is challenging, so gold-catalyzed cross-couplings are rare. The (MeDalphos)AuCl complex, which we showed was prone to undergo oxidative addition, is reported here to efficiently catalyze the C-N coupling of aryl iodides and amines. The transformation does not require an external oxidant or a directing group. It is robust and works with a wide scope of aryl iodides and N-nucleophiles under mild conditions. Mechanistic studies, including the NMR and MS characterization of a key aryl amido Au(iii) complex, strongly support a 2e redox cycle in which oxidative addition precedes transmetalation and reductive elimination is the rate-determining step.

Eco-friendly solvents for palladium-catalyzed desulfitative C-H bond arylation of heteroarenes

Herein, we report the Pd-catalyzed regioselective direct arylation of heteroarenes in which benzenesulfonyl chlorides are used as coupling partners through a desulfitative cross-coupling that can be performed in diethyl carbonate (DEC) or cyclopentyl methyl ether (CPME) as green and renewable solvents or even in neat conditions instead of dioxane or dimethylacetamide (DMA). Under these solvent conditions, the reaction proceeds with a wide range of heteroarenes. C2- or C5-arylated products were obtained with furan and pyrrole derivatives. Benzofuran was also arylated regioselectively at the C2-position, whereas the reaction proceeds selectively at the C3- or C4-positions if thiophenes and benzothiophenes are used. Moreover, in some cases, especially with 1-methylindole, solvent-free conditions afforded better regioselectivities and/or yields than the reaction performed in the presence of solvents.