90725-49-8

Usage

Uses

Used in Organic Synthesis:
5-bromo-3-methylindolin-2-one is used as a key intermediate in organic synthesis for the production of various pharmaceuticals and chemical compounds. Its unique structure, including the bromine and methyl groups, allows for versatile chemical reactions, facilitating the creation of a wide array of derivatives with potential applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 5-bromo-3-methylindolin-2-one is utilized as a starting material for the development of new drugs. Its pharmacological properties are under investigation, with a focus on its potential as a therapeutic agent for treating various diseases. 5-bromo-3-methylindolin-2-one's structure provides a foundation for the design of novel molecules with improved efficacy and selectivity.
Used in Pharmaceutical Research and Development:
5-bromo-3-methylindolin-2-one is employed as a target for research and development in pharmaceutical sciences. Its presence in the scientific community is due to the compound's potential to influence reactivity and biological activities, making it a valuable asset in the discovery of new therapeutic agents and the advancement of existing treatments.
Used in Drug Design:
As a component in drug design, 5-bromo-3-methylindolin-2-one is used to create new molecular entities with specific therapeutic targets. 5-bromo-3-methylindolin-2-one's structural attributes, such as the bromine atom, can be leveraged to enhance the drug's pharmacokinetic and pharmacodynamic profiles, leading to more effective and safer medications.
Used in Chemical Biology:
In chemical biology, 5-bromo-3-methylindolin-2-one serves as a tool for probing biological systems and understanding the mechanisms of action of various biologically active molecules. Its unique chemical properties allow researchers to investigate its interactions with biological targets, offering insights into potential therapeutic applications and the underlying biology of diseases.

Upstream product

• 20870-78-4 5-bromo-2-indolin-2-one 
• 74-88-4 methyl iodide 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 1536478-47-3 N-(4-bromo-2-vinylphenyl)formamide 
• 71861-99-9 formic acid-(2,4-dibromo-anilide) 
• 13939-06-5 molybdenum hexacarbonyl 
• 87-48-9 5-Bromo-1H-indole-2,3-dione 
• 90725-57-8 (±)-5-bromo-3-hydroxy-3-methylindolin-2-one 
• 67-56-1 methanol 
• 10075-48-6 5-bromo-3-methyl-1H-indole 
• 29124-56-9 1-(2-amino-5-bromophenyl)ethanone 
• 59-48-3 2-oxoindole 
• 1504-06-9 3-methylindolin-2-one 

Downstream Products

• 1094900-76-1 5-bromo-1-diphenylacetyl-3-methyloxindole 
• 1141508-79-3 3-methyl-5-(3-trifluoromethylphenyl)-1,3-dihydroindol-2-one 
• 1160644-99-4 (S)-3-[(S)-1-(p-methylbenzenesulfonylamino)-1-phenylmethyl]-5-bromo-3-methylindolin-2-one 
• 1310861-90-5 (R)-5-bromo-3-(hydroxy(phenyl)amino)-3-methylindolin-2-one 
• 1353717-77-7 (S)-5-bromo-3-(hydroxy(phenyl)amino)-3-methylindolin-2-one 
• 1297848-03-3 3-(bis(4-(dimethylamino)phenyl)methyl)-5-bromo-3-methylindolin-2-one 
• 1227411-64-4 5-bromo-3-(1-hydroxy-2-oxo-2-phenylethyl)-3-methylindolin-2-one 
• 516517-21-8 5-(3-chloro-phenyl)-3-methyl-1,3-dihydro-indol-2-one 

Relevant academic research and scientific papers

Synergistic Ir/Cu Catalysis for Asymmetric Allylic Alkylation of Oxindoles: Enantio- and Diastereoselective Construction of Quaternary and Tertiary Stereocenters

3,3-Disubstituted oxindoles bearing quaternary and tertiary stereogenic centers are privileged structural motifs, which widely exist in pharmaceutical and natural products. Herein, a highly regio-, enantio-, and diastereoselective allylic alkylation of 3-alkyl oxindoles through synergistic iridium and copper catalysis is described, which provides a series of 3,3-disubstituted oxindole derivatives containing adjacent quaternary and tertiary stereogenic centers in excellent yields, enantiomeric excess, and diastereomeric ratio (for 30 examples, up to 97 % yield, >99 % ee, and >20 : 1 dr). This method provides exclusive branched selectivity, excellent enantio- and diastereoselectivities, and good functional compatibility. Control experiments suggested that the chiral copper catalyst is required for achieving high reactivities and diastereoselectivities under mild reaction conditions.

Rapid Oxidation Indoles into 2-Oxindoles Mediated by PIFA in Combination with n-Bu4NCl ? H2O

We report the development of a rapid approach for directly converting indoles into 2-oxindoles promoted by HOCl formed in situ from the combination of (bis(trifluoroacetoxy) iodo)benzene (PIFA) and n-Bu4NCl ? H2O. The procedure is widely functional group tolerant and provides 2-oxindoles in up to 95% yield within 5 min. The potential applications of the developed methodology are demonstrated by the gram-scale preparation of 3-methyl-2-oxindole (11 a), the one-pot two-step syntheses of spiro-oxindoles 26 a and 26 b, and the formal synthesis of (-)-folicanthine (2). (Figure presented.).

Iron-Catalyzed Methylation Using the Borrowing Hydrogen Approach

A general iron-catalyzed methylation has been developed using methanol as a C1 building block. This borrowing hydrogen approach employs a Kn?lker-type (cyclopentadienone)iron carbonyl complex as catalyst (2 mol %) and exhibits a broad reaction scope. A variety of ketones, indoles, oxindoles, amines, and sulfonamides undergo mono- or dimethylation in excellent isolated yields (>60 examples, 79% average yield).

Preparation method of 3-substituted oxidized indole and derivative

The invention belongs to the technical field of organic chemistry and pharmaceutical chemistry and particularly relates to a method of preparing 3-substituted oxidized indole and a derivative. In themethod, with a 3-substituted indole derivative as a raw material and one or more of a tetrabutyl ammonium halide compound/sodium chloride/sodium iodide/potassium iodide as additives, and one or more of dichloromethane/1,2-dichloroethane/tetrahydrofurane/methylbenzene/1,4-dioxane/ethyl acetate/methanol are added as solvents; then one or more of [bis(trifluoroacetoxyl)iodine]benzene/iodosobenzene diacetate are added as oxidants in order to carry out a reaction with reaction temperature being controlled, thus producing the 3-substituted oxidized indole derivative. The method has gentle reaction conditions, simple operations, short reaction time and high yield, and is free of a metal catalyst and is environment-friendly.

Tetrabutylammonium Iodide-promoted thiolation of oxindoles using sulfonyl chlorides as sulfenylation reagents

3-Sulfanyloxindoles were synthesised by triphenylphosphine-mediated transition-metal-free thiolation of oxindoles using sulfonyl chlorides as sulfenylation reagents. The above reaction was promoted by iodide anions, which was ascribed to the in situ conversion of sulfenyl chlorides into the more reactive sulfenyl iodides. Moreover, the thiolation of 3-aryloxindoles was facilitated by bases. The use of a transition-metal-free protocol, readily available reagents, and mild reaction conditions make this protocol more practical for preparing 3-sulfanyloxindoles than traditional methods.

PURINE INHIBITORS OF HUMAN PHOSPHATIDYLINOSITOL 3-KINASE DELTA

The instant invention provides compounds of formula (I) which are PI3K-delta inhibitors, and as such are useful for the treatment of PI3K-delta-mediated diseases such as inflamation, asthma, COPD and cancer.

Magnesium-Catalyzed Electrophilic Trifluoromethylation: Facile Access to All-Carbon Quaternary Centers in Oxindoles

The first example of a magnesium-catalyzed direct trifluoromethylation of 3-substituted oxindoles using an electrophilic hypervalent iodine reagent is reported. The reaction proceeds under unprecedented mild conditions leading to the formation of an all-carbon quaternary center in oxindoles in high chemical yield and demonstrates excellent functional group tolerance. In addition to trifluoromethyl, other perfluoroalkyl groups can be introduced with similar level of efficacy. Mechanistic investigations are consistent with the involvement of a radical pathway. The chemical versatility of the obtained products is further illustrated through their conversion in situ into valuable organofluorine building blocks, making the protocol more widely applicable.

Molybdenum hexacarbonyl mediated synthesis of indolin-2-one & azaindolin-2-one under catalyst free conditions

Syntheses of indolin-2-ones and azaindolin-2-ones have been realized. The strategy involves the formation of tosylhydrazone from tosylhydrazine and 2-amino aryl or pyridyl aldehydes/ketones which then undergo intramolecular aminocarbonylation to afford indolin-2-ones and azaindolin-2-ones. The generality of the method was demonstrated by synthesizing C3 substituted and unsubstituted indolin-2-one and azaindolin-2-one derivatives.

BICYLIC COMPOUNDS AS MODULATORS OF RORGAMMA

The present invention encompasses compounds of the formula (I): wherein the variables are defined herein which are suitable for the modulation of RORC and the treatment of diseases related to the modulation of RORC. The present invention also encompasses

Regiodivergent access to five- and six-membered benzo-fused lactams: Ru-catalyzed olefin hydrocarbamoylation

We report herein a new strategy of the Ru-catalyzed intramolecular olefin hydrocarbamoylation for the regiodivergent synthesis of five- and six-membered benzo-fused lactams starting from N-(2-alkenylphenyl)formamides. Using a combined catalyst of Ru3