1196-79-8

Usage

Uses

Used in Pharmaceutical Industry:
2,5-Dimethylindole is used as a reactant for the stereoselective synthesis of indolines via palladium-catalyzed asymmetric hydrogenation of unprotected indoles. This application is crucial in the development of new pharmaceutical compounds with specific stereochemistry, which can lead to improved drug efficacy and reduced side effects.
Used in Chemical Synthesis:
2,5-Dimethylindole is used as a reactant in the stereoselective preparation of substituted indoles through rhodium-catalyzed enantioselective coupling reactions with diazo compounds. This process is essential in creating novel indole-based molecules with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Material Science:
2,5-Dimethylindole is employed as a reactant in the enantioselective synthesis of fluorene derivatives via Friedel-Crafts reactions. These fluorene-based compounds find applications in the development of advanced materials, such as organic light-emitting diodes (OLEDs) and other optoelectronic devices.
Used in Organic Chemistry:
2,5-Dimethylindole is used as a reactant in the preparation of bis-indolyldihydroxybenzoquinones by the addition of indoles to dichlorobenzoquinone, promoted by a Bronsted acid. This reaction is significant in the synthesis of complex organic molecules with potential applications in various fields, including pharmaceuticals, agrochemicals, and natural products.
Used in Research and Development:
2,5-Dimethylindole is utilized in reactions with hydroxypyrazolines, which can lead to the formation of novel compounds with potential applications in various industries. This reaction is particularly useful in research and development settings, where new compounds are constantly being explored for their potential uses and properties.

Sources

https://www.sigmaaldrich.com/catalog/product/aldrich/d166006?lang=en®ion=US https://books.google.com/books?isbn=0470188073

InChI:InChI=1/C10H11N/c1-7-3-4-10-9(5-7)6-8(2)11-10/h3-6,11H,1-2H3

Upstream product

• 1077-21-0 acetone 4-methylphenylhydrazone 
• 2050-43-3 N-(2,4-dimethylphenyl)acetamide 
• 141-52-6 sodium ethanolate 
• 122-20-3 triisopropanolamine 
• 106-49-0 p-toluidine 
• 29289-13-2 2-iodo-4-methylaniline 
• 889943-11-7 C₁₁H₁₁NO₂ 
• 637-60-5 p-tolylhydrazine hydrochloride 
• 67-64-1 acetone 
• 38939-88-7 2-chloro-4-methyl-1-nitrobenzene 
• 102052-38-0 1-(5-methyl-2-nitrophenyl)propan-2-one 
• 700836-86-8 1-benzenesulfonyl-2,5-dimethyl-1H-indole 
• 116325-12-3 5-methyl-1-(phenylsulfonyl)-1H-indole 
• 614-96-0 5-methyl-1H-indole 

Downstream Products

• 5435-40-5 2,5-Dimethyl-indol-3-essigsaeure 
• 116436-12-5 4-methyl-2-propyl-aniline 
• 90874-56-9 (±)-2,5-dimethylindoline 
• 53165-17-6 N-(2-formyl-4-methylphenyl)acetamide 
• 67081-68-9 2-acetamido-5-methylbenzoic acid 
• 77510-26-0 3-(2-hydroxy-2-indane-1,3-dionyl)-2,5-dimethylindole 
• 64137-76-4 2,5-dimethyl-3-(phenylthio)-1H-indole 
• 1644666-87-4 (2R,3R)-3-benzyl-2,5-dimethylindoline 
• 61364-25-8 2,5-dimethyl-1H-indole-3-carboxaldehyde 

Relevant academic research and scientific papers

Cobalt-Catalyzed Dearomatization of Indoles via Transfer Hydrogenation to Afford Polycyclic Indolines

A cobalt-catalyzed dearomatization of indoles via transfer hydrogenation with HBpin and H2O has been developed. This reaction offered a straightforward platform to access hexahydropyrido[1,2-a]indoles in high regio- and chemoselectivity. A preliminary reaction mechanism was proposed on the basis of deuterium-labeling experiments, and a cobalt hydride species was involved in the reaction.

Decarboxylation of indole-3-carboxylic acids under metal-free conditions

Two reaction systems have been developed for the decarboxylation of indole-3-carboxylic acids. The decarboxylation can be achieved smoothly under K2CO3-catalyzed or acetonitrile-promoted basic conditions. It provided an efficient and simple method for the transformation of indole-3-carboxylic acids and the corresponding indoles were isolated with good to excellent yields. From the experimental facts, we put forward the possible reaction mechanism.

Palladium-Catalyzed Oxidation-Hydroxylation and Oxidation-Methoxylation of N -Boc Indoles for the Synthesis of 3-Oxoindolines

The palladium-catalyzed oxidation-hydroxylation and oxidation-methoxylation of N -Boc indoles for the synthesis of tert -butyl 2-hydroxy(methoxy)-3-oxoindoline-1-carboxylates and their derivatives is developed. The process occurs readily using PdCl 2 as the catalyst and acetonitrile as the solvent to afford 3-oxoindolines in moderate to high yields. A mechanism for this Pd-catalyzed oxidation-hydroxylation and oxidation-methoxylation of N -Boc indoles is proposed.

Method for preparing indole and derivatives thereof

The invention discloses a method for preparing indole and derivatives of indole. The method for preparing indole and the derivatives of indole is characterized by comprising the following two steps that (1) a catalyst, a ligand and alkali are added in a reaction tube, under the protection of nitrogen, beta-hydroxy ketone or ester is reacted with a mixed solution of o-nitro aryl halides for 3 to 8h in an oil bath pan at the temperature of 90 to 120 DEG C, and then cooled to room temperature after reaction, and extracted, washed, dried and subjected to chromatography to obtain a product of o-nitro alpha-aryl ketone or ester; (2) o-nitro alpha-aryl ketone or ester obtained in the step (1), a reducing agent system and a solvent are added to the reaction tube, and reacted for 3 to 8h at the temperature of 60 to 100 DEG C, and then extracted, washed, dried and subjected to chromatography after being reacted to obtain a target product of indole and the derivatives of indole. Reaction raw materials, the catalyst, the ligand, the alkali and the solvent used in the invention are all industrial commodities, and simple and readily available, wide in sources, cheap in price, and further very stable in performances, and with no need for special storage conditions; in addition, the method for preparing indole and the derivatives of indole disclosed by the invention has the characteristics of low cost, high yield, simple process, less pollution and the like.

Divergent synthesis of indoles, oxindoles, isocoumarins and isoquinolinones by general Pd-catalyzed retro-aldol/α-arylation

Divergent synthesis of indoles, oxindoles, isocoumarins and isoquinolinones is described in this report by using a general Pd-catalyzed tandem reaction of β-hydroxy carbonyl compounds with aryl halides bearing an ortho-nitro, -ester or -cyano substituent. A key retro-aldol/α-arylation reaction is involved that merges classic Pd cross-coupling chemistry with novel Pd-promoted retro-aldol C-C activation to produce α-arylated ketones or esters. Subsequent intramolecular condensation of the carbonyl with the ortho-synthon gives target heterocycles. The use of common, commercially available and cheap substrates and catalyst system adds additional synthetic advantages to the conceptual significance.

Discovery of a First-in-Class, Potent, Selective, and Orally Bioavailable Inhibitor of the p97 AAA ATPase (CB-5083)

The AAA-ATPase p97 plays vital roles in mechanisms of protein homeostasis, including ubiquitin-proteasome system (UPS) mediated protein degradation, endoplasmic reticulum-associated degradation (ERAD), and autophagy. Herein we describe our lead optimization efforts focused on in vitro potency, ADME, and pharmaceutical properties that led to the discovery of a potent, ATP-competitive, D2-selective, and orally bioavailable p97 inhibitor 71, CB-5083. Treatment of tumor cells with 71 leads to significant accumulation of markers associated with inhibition of UPS and ERAD functions, which induces irresolvable proteotoxic stress and cell death. In tumor bearing mice, oral administration of 71 causes rapid accumulation of markers of the unfolded protein response (UPR) and subsequently induces apoptosis leading to sustained antitumor activity in in vivo xenograft models of both solid and hematological tumors. 71 has been taken into phase 1 clinical trials in patients with multiple myeloma and solid tumors.

3-(o-Trifluoroacetamidoaryl)-1-propargylic esters: common intermediates for the palladium-catalyzed synthesis of 2-aminomethyl-, 2-vinylic, and 2-alkylindoles

3-(o-Trifluoroacetamidoaryl)-1-propargylic esters have been used as common synthetic intermediates for the preparation of a variety of 3-unsubstituted 2-substituted indoles. Treating ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates unsubstituted or containing an aryl substituent at the propargylic carbon with piperazines and Pd(PPh3)4 in THF at 80 °C affords 2-(piperazin-1-ylmethyl)indoles in excellent yields. Good to excellent yields of 2-aminomethylindoles are also obtained with other secondary amines. Ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates bearing an alkyl substituent at the propargylic carbon and ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic acetates disubstituted at the propargylic carbon give 2-vinylic indoles with the Pd(OAc)2/PPh3 combination and Et3N in THF at 80 °C. Formation of 2-vinylic indoles is quite stereoselective, generating trans vinylic derivatives, at least with the substrates that we have investigated. In the presence of formic acid, Et3N, and Pd(PPh3)4 in MeCN at 80 °C, ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates afford 2-alkylindoles in good to excellent yields.

Pd PEPPSI-IPr-mediated reactions in metal-coated capillaries under MACOS: The synthesis of indoles by sequential aryl amination/heck coupling

A method has been devised for the microwave-assisted, continuous-flow preparation of indole alkaloids by a two-step aryl amination/cross-coupling sequence of bromoalkenes and 2-bromoanilines. This process requires both the presence of a metal-lined flow tube (a 1180 micron capillary) and the Pd PEPPSI-IPr catalyst; without either, the catalyst or the film, there is zero turnover of this catalytic process. A silver film has been shown to provide some conversion (48-62%), but optimal results (quantitative) across a variety of bromoalkenes and bromoanilines were achieved by using a highly porous palladium film. Possible roles for the Pd film are considered, as is the interplay of the catalyst and the film.

2-Alkylindoles via palladium-catalyzed reductive cyclization of ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonates

The reaction of ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonates with formate anions in the presence of Pd(PPh3)4 affords 2-alkylindoles in good to excellent yields.

Ruthenium-catalyzed heteroannulation of anilines with alkanolammonium chlorides leading to indoles

Anilines react with alkanolammonium chlorides in an aqueous medium (H2O-dioxane) at 180°C in the presence of a catalytic amount of a ruthenium catalyst together with SnCl2·2H2O to afford the corresponding indoles in moderate to good yields. Especially, when triisopropanolammonium chloride is employed to react with anilines, 2-methylindoles are formed regioselectively. The presence of SnCl2·2H2O is necessary for the effective formation of indoles. A reaction pathway involving alkanol group transfer from alkanolamines to anilines, N-alkylation of anilines by anilinoalkanols and heteroannulation of 1,2-dianilinoalkanes is proposed for this catalytic process.