20870-90-0

Usage

Uses

Used in Organic Synthesis:
5-Bromo-1-methyl-2-oxoindoline is used as a valuable intermediate in the field of organic synthesis for the preparation of a range of complex organic molecules. Its unique structural features make it a versatile building block for the development of novel compounds with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-Bromo-1-methyl-2-oxoindoline is used as a key intermediate for the synthesis of symmetric cyclic indole-tetramers. These indole-tetramers have been found to possess significant biological activities, including potential applications in the treatment of various diseases and disorders.
Used in Chemical Research:
5-Bromo-1-methyl-2-oxoindoline is also utilized in chemical research as a starting material for the preparation of substituted oxindoles. These substituted oxindoles are important scaffolds in the development of new drugs and pharmaceutical agents, as they can exhibit a wide range of biological activities, such as anti-inflammatory, analgesic, and anti-cancer properties.

InChI:InChI=1/C9H8BrNO/c1-11-8-3-2-7(10)4-6(8)5-9(11)12/h2-4H,5H2,1H3

Upstream product

• 1384521-02-1 2-diazo-N-(4-bromophenyl)-N-methylacetamide 
• 6911-87-1 4-bromo-N-methylaniline 
• 10075-52-2 5-bromo-1-methyl-H-indole 
• 87-48-9 5-Bromo-1H-indole-2,3-dione 
• 74-88-4 methyl iodide 
• 38118-70-6 2-diazo-N-methyl-N-phenylacetamide 
• 100-61-8 N-methylaniline 
• 2058-72-2 5-bromo-1-methyl-1H-indole-2,3-dione 
• 61-70-1 N-methyl-2-indolinone 

Downstream Products

• 1027233-55-1 5-Bromo-1-methyl-2-thioxo-2,3-dihydro-1H-indole-3-carboxylic acid phenylamide 
• 1596355-35-9 ethyl (3S)-5-bromo-3-[(3S)-2,5-dioxo-1-phenylpyrrolidin-3-yl]-1-methyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylate 
• 69736-60-3 5-bromo-3-(hydroxyimino)-1-methylindolin-2-one 

Relevant academic research and scientific papers

An atypical easy reductive cleavage of the conjugated CC bond in 1,1′-disubstituted isoindigos under the action of aqueous hydrazine hydrate

The reaction of diverse symmetrically-substituted isoindigo derivatives with 80% aqueous hydrazine hydrate is described. The influence of the structure of the substituent on either oxindole or isatin-3-hydrazone formation is discussed.

3-Carboxamide oxindoles as 1,3-C,N-bisnucleophiles for the highly diastereoselective synthesis of CF3-containing spiro-δ-lactam oxindoles featuring acyl at the ortho-position of spiro carbon atom

A simple and efficient strategy has been established for the synthesis of δ-lactam fused oxindoles via the Michael/N-hemiketalization cascade reaction of 3-carboxamide oxindoles and α,β-unsaturated trifluoromethyl ketones. A wide range of structurally novel CF3-containing spiro-δ-lactam oxindoles featuring acyl at the ortho-position of spiro carbon atoms were obtained in moderate to good yields with excellent diastereoselectivities under mild conditions. This work represents the first example of a systematic study of 3-carboxamide oxindoles as 1,3-C,N bisnucleophiles.

Synthesis of Oxindole Derivatives via Intramolecular C–H Insertion of Diazoamides Using Ru(II)-Pheox Catalyst

This work presented the efficient intramolecular aromatic C–H insertion of diazoacetamide. The 1a–1o diazo compounds (except for 1k) were converted into their corresponding oxindoles via an intramolecular C–H insertion reaction in the presence of a Ru catalyst. The Ru-Pheox catalyst was shown to be highly efficient in this transformation in terms of the regioselectivity, producing the desired products in excellent yield (99%). The efficiency of the Ru catalyst reached 580 (TON) and 156 min?1 (TOF).

Acylation of oxindoles using methyl/phenyl estersviathe mixed Claisen condensation - an access to 3-alkylideneoxindoles

Predominantly, aggressive acid chlorides and stoichiometric coupling reagents are employed in the acylating process for synthesizing carbonyl tethered heterocycles. Herein, we report simple acyl sources,viz. methyl and phenyl esters, which acylate oxindolesviathe mixed Claisen condensation. This straightforward protocol is mediated by LiHMDS and KOtBu and successfully applied to a wide range of substrates. It is a noteworthy transformation that skips the stepwise generation of enolates and acylation, and the reaction is performed at a moderate temperature with no side reactions. This protocol produces the first examples ofortho-substituents in an aryl ring flanked with electron-donating and electron-withdrawing substrates. Interestingly, robust organometallic ferrocenyl methyl ester cleaved under these conditions with ease. Furthermore, biologically important Tenidap's analog was synthesized by this protocol.

Candida antarctica lipase-B-catalyzed kinetic resolution of 1,3-dialkyl-3-hydroxymethyl oxindoles

Candida antarctica (CAL-B) lipase-catalyzed resolution of 1,3-dialkyl-3-hydroxymethyl oxindoles has been performed to obtain (R)-1,3-dialkyl-3-acetoxymethyl oxindoles with up to 99% ee and (S)-1,3-dialkyl-3-hydroxymethyl oxindoles with up to 78% ee using vinyl acetate as acylating agent and acetonitrile as solvent transforming (S)-3-allyl-3-hydroxymethyl oxindole to (3S)-1′-benzyl-5-(iodomethyl)-4,5-dihydro-2H-spiro[furan-3,3′-indolin]-2′-one. The optically active 3-substituted-3-hydroxymethyl oxindoles and spiro-oxindoles are among the key synthons in the synthesis of potentially biologically active molecules.

Synthesis of 2-Oxindoles from Substituted Indoles by Hypervalent-Iodine Oxidation

A practical conversion of indoles into the corresponding 2-oxindoles is achieved efficiently using a hypervalent iodine reagent. This oxidation is amenable to different substituted indoles, and allows the synthesis of a wide range of synthetically valuable substituted 2-oxindoles in up to 90 % yield. Furthermore, Ropinirole, a drug used to alleviate the symptoms of Parkinson's disease, was synthesized in three steps in an overall yield of 44 % using this method.

Method for directly synthesizing substituted 2-indolone by substituted indole under neutral condition

The invention relates to a method for directly synthesizing substituted 2-indolone by substituted indole under the neutral condition. The method comprises the following steps of sequentially adding organic solvents and water according to the proportion of 1:1-1:20 at the room temperature; then, adding high-iodine reagents; raising the temperature to 40 to 160 DEG C; then, adding indole; performingreaction for 1 to 8 hours to obtain the substituted 2-indolone compounds. The method has the main innovation point that under the neutral condition, substituted 2-indolone is directly synthesized through indole oxidization; the use of strong acid reagents is avoided. The method has the advantages that the raw materials are cheap and can be easily obtained; the operation is simple and convenient;the substrate universality is high; the reaction yield is high, and the like.

Method for synthesizing indole-2-ketone compound

The invention belongs to the technical field of organic chemical synthesis, and particularly relates to a method for synthesizing an indole-2-ketone compound. Indole-2-ketone compound synthesis is difficultly industrialized due to the problems of poor yield, cost and environmental protection in the prior art, the method includes the steps: taking a compound X as a catalyst in a hydrous organic solvent; performing reaction on indole and water under the condition of oxidizing agents to obtain the indole-2-ketone compound. The compound X is preferably iodine, and the indole-2-ketone compound is applicable to the field of organic synthesis and medicine.

Cinchona-alkaloid-catalyzed enantioselective hydroxymethylation of 3-fluorooxindoles with paraformaldehyde

Cinchona-alkaloid-catalyzed hydroxymethylation of 3-fluorooxindoles using paraformaldehyde as the C1 unit was achieved. A wide range of 3-fluorooxindoles was successfully reacted to give the corresponding 3-fluoro-3-hydroxymethyloxindoles with high efficiency and moderate to good enantioselectivity.

Transition-metal-free Chemoselective Oxidative C?C Coupling of the sp3 C?H Bond of Oxindoles with Arenes and Addition to Alkene: Synthesis of 3-Aryl Oxindoles, and Benzofuro- and Indoloindoles

A transition-metal (TM)-free and halogen-free NaOtBu-mediated oxidative cross-coupling between the sp3 C?H bond of oxindoles and sp2 C?H bond of nitroarenes has been developed to access 3-aryl substituted and 3,3-aryldisubstituted oxindoles in DMSO at room temperature in a short time. Interestingly, the sp3 C?H bond of oxindoles could also react with styrene under TM-free conditions for the practical synthesis of quaternary 3,3-disubstituted oxindoles. The synthesized 3-oxindoles have also been further transformed into advanced heterocycles, that is, benzofuroindoles, indoloindoles, and substituted indoles. Mechanistic experiments of the reaction suggests the formation of an anion intermediate from the sp3 C?H bond of oxindole by tert-butoxide base in DMSO. The addition of nitrobenzene to the in-situ generated carbanion leads to the 3-(nitrophenyl)oxindolyl carbanion in DMSO which is subsequently oxidized to 3-(nitro-aryl) oxindole by DMSO.