36797-43-0

Basic information

• Product Name: 3-methyl-1-p-toluenesulfonyl-1H-indole
• Synonyms: 3-methyl-1-p-toluenesulfonyl-1H-indole
• CAS NO: 36797-43-0
• Molecular Formula: C₁₆H₁₅NO₂S
• Molecular Weight: 285
• Mol File: 36797-43-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-methyl-1-p-toluenesulfonyl-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methyl-1-p-toluenesulfonyl-1H-indole(36797-43-0)
• EPA Substance Registry System: 3-methyl-1-p-toluenesulfonyl-1H-indole(36797-43-0)

Safety Data

• Hazardous Substances Data: 36797-43-0(Hazardous Substances Data)

Upstream product

• 83-34-1 3-Methylindole 
• 98-59-9 p-toluenesulfonyl chloride 
• 1859-70-7 N-(2-acetylphenyl)-4-methylbenzenesulfonamide 
• 108-24-7 acetic anhydride 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 66-25-1 hexanal 
• 106-95-6 allyl bromide 
• 944546-69-4 (E)-N-(2-(1-chloroprop-1-en-2-yl)phenyl)-4-methylbenzenesulfonamide 
• 106745-67-9 N-(2-(1-methylethenyl)phenyl)-4-methylbenzenesulfonamide 
• 551-93-9 2-aminoacetophenone 
• 41253-27-4 sodium salt of 3-methylindole 
• 52562-19-3 2-isopropenylaniline 
• 1073354-51-4 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-p-toluenesulfonyl-1H-indole 
• 74-88-4 methyl iodide 

Downstream Products

• 74786-94-0 C₃₀H₂₅NO₆S 
• 83-34-1 3-Methylindole 
• 727416-63-9 (R)-3-methyl-1-(p-toluenesulfonyl)indoline 
• 727416-57-1 (S)-(+)-3-methyl-N-(p-toluenesulfonyl)indoline 
• 299914-39-9 3-methyl-1-(4-nitrophenyl)-1H-indole 
• 1045601-63-5 3-methyl-1-(2-nitro-phenyl)-1H-indole 
• 1218989-80-0 butyl (E)-3-(3-methyl-1-(4-methylbenzene-sulfonyl)-1H-indol-2-yl)acrylate 
• 875-30-9 1,3-dimethylindole 

Relevant articles and documents

Synthesis of a Novel Type of 2,3′-BIMs via Platinum-Catalysed Reaction of Indolylallenes with Indoles

Optimisation, scope and mechanism of the platinum-catalysed addition of indoles to indolylallenes is reported here to give 2,3′-BIMs with a novel core structure very relevant for pharmaceutical industry. The reaction is modulated by the electronic properties of the substituents on both indoles, with the 2,3′-BIMs favoured when electron donating groups are present. Although simple at first, a complex mechanism has been uncovered that explains the different behaviour of these systems with platinum when compared with other metals (e.g. gold). Detailed labelling studies have shown Pt-catalysed 6-endo-trig cyclisation of the indollylallene as the first step of the reaction and the involvement of two cyclic vinyl-platinum intermediates in equilibrium through a platinum carbene, as the key intermediates of the catalytic cycle towards the second nucleophilic attack and formation of the BIMs.

Palladium-catalysed annulative allylic alkylation for the synthesis of benzannulated heteroarenes

A conceptually novel intramolecular allylic alkylation strategy is developed for the synthesis of carbazoles and dibenzothiophenes. In an unusual event, palladium catalyses the formation of π-allylpalladium complexes of the respective (2-methylindol-3-yl)allyl acetates and subsequently facilitates the benzannulation process. This journal is

Electrocatalytic Dehydrogenative Cyclization of 2-Vinylanilides for the Synthesis of Indoles

Indole is prevalent in bioactive compounds and natural products. The development of efficient and sustainable methods to access this privileged structural scaffold has been a long-standing interest of synthetic chemists. Herein, we report an electrocataly

Electron Transfer Photoredox Catalysis: Development of a Photoactivated Reductive Desulfonylation of an Aza-Heteroaromatic Ring

Herein, we report a protocol for desulfonylation of aza-heteroaromatic rings via photoinduced electron transfer and hydrogen atom transfer. This general protocol has a wide substrate range and moderate to good yields. The utility of the method was demonstrated by the chemoselective desulfonylation of a molecule containing both an aliphatic and an aromatic sulfonamide. (Figure presented.).

Reductive aromatization of oxindoles to 3-substituted indoles

A practical and scalable approach for the synthesis of 3-substituted indoles is delineated via hydride nucleophilic addition to 3-substituted-2-oxindoles. The reaction proceeds through reductive aromatization involving indolinium ion intermediate. A wide range of 3-functionalized indoles have been synthesized. The method is employed for the synthesis of 3,3?-bis-indoles and a dimeric 3-indole derivative. Moreover, this protocol is used to obtain naturally occuring amino acid tryptamine.

Palladium-Catalyzed Methylation of Aryl, Heteroaryl, and Vinyl Boronate Esters

A method for the direct methylation of aryl, heteroaryl, and vinyl boronate esters is reported, involving the reaction of iodomethane with aryl-, heteroaryl-, and vinylboronate esters catalyzed by palladium and PtBu2Me. This transformation occurs with a remarkably broad scope and is suitable for late-stage derivatization of biologically active compounds via the boronate esters. The unique capabilities of this method are demonstrated by combining carbon-boron bond-forming reactions with palladium-catalyzed methylation in a tandem transformation.

Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles

A variety of 3-substituted and 2,3-disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2-alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3-acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5-dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2-a]carbazole scaffold was prepared in good yield in six steps from commercial ortho-iodoaniline. (Figure presented.).

Fluorine as a Traceless Directing Group for the Regiodivergent Synthesis of Indoles and Tryptophans

Despite ample evidence for the unique reactivity offered by hypervalent F-iodanes, mechanistic investigations fall far behind. In order to shed light on the unusual behavior of such F-reagents, we conducted computational and experimental studies on the chemodivergent transformation of styrenes. We identified the spirocyclic F-cyclopropane as the common intermediate for both the C,H-fluorination and C,H-amination pathways. The fate of this key compound is determined by the extent of cationic charge delocalization controlled by the N-substituents. Exploiting this phenomenon, a multitude of different transformations have become available, leading, i.e., to the regiodivergent synthesis of indoles and tryptophans.

Palladium-Catalyzed Formal (5 + 2) Annulation between ortho-Alkenylanilides and Allenes

2-Alkenyltriflylanilides react with allenes upon treatment with catalytic amounts of Pd(OAc)2 and Cu(II) to give highly valuable 2,3-dihydro-1H-benzo[b]azepines, in good yields, and with very high regio- and diastereoselectivities. Density functional theory (DFT) calculations suggest that the C-H activation of the alkenylanilide involves a classical concerted metalation-deprotonation (CMD) mechanism.

Catalytic, Interrupted Formal Homo-Nazarov Cyclization with (Hetero)arenes: Access to α-(Hetero)aryl Cyclohexanones

The first examples of a Lewis-acid catalyzed (hetero)arene interrupted, formal homo-Nazarov cyclization have been disclosed. Using SnCl4 as the catalyst, alkenyl cyclopropyl ketones undergo ring-opening cyclization to form six-membered cyclic oxyallyl cations. Subsequent intermolecular Friedel-Crafts-type arylation with various electron-rich arenes and heteroarenes provides functionalized α-(hetero)arylated cyclohexanones, a scaffold present in many natural products and bioactive compounds, in yields up to 88% and diastereomeric ratios up to 12:1. Regiospecific arylation occurs at the α-carbon of the oxyallyl cation due to polarization caused by the ester group.