90537-20-5

Usage

Uses

Used in Pharmaceutical Industry:
2H-Indol-2-one, 5-chloro-1,3-dihydro-3-Methylis utilized as an intermediate in the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs, particularly those targeting specific biological activities.
Used in Agrochemical Industry:
In the agrochemical sector, 2H-Indol-2-one, 5-chloro-1,3-dihydro-3-Methylserves as an intermediate for the production of agrochemicals. Its potential role in this industry highlights its versatility and the possibility of contributing to the development of new pesticides or other agricultural products.
Used in Scientific Research:
2H-Indol-2-one, 5-chloro-1,3-dihydro-3-Methylhas been studied for its potential biological activities, such as antifungal and anticancer properties. Researchers are interested in exploring its capabilities in inhibiting the growth of fungi and cancer cells, which could lead to the discovery of new treatments and therapies.
Used in Enzyme Inhibition Applications:
2H-Indol-2-one, 5-chloro-1,3-dihydro-3-Methylhas demonstrated inhibitory effects on certain enzymes, suggesting its potential use in various industries where enzyme regulation is crucial. This could include applications in the development of new drugs, as well as in other fields where controlling enzyme activity is beneficial.

Upstream product

• 17630-75-0 5-chloro-indolin-2-one 
• 17630-76-1 5-chloroindole 2,3-dione 
• 201230-82-2 carbon monoxide 
• 112768-02-2 4-chloro-1-nitro-2-vinylbenzene 
• 67-56-1 methanol 
• 71095-42-6 5-chloro-3-methyl-1H-indole 
• 63007-54-5 N-(2-bromo-4-chlorophenyl)formamide 
• 1536478-45-1 N-(4-chloro-2-vinylphenyl)formamide 
• 86790-37-6 methyl α-methyl-5-chloro-2-nitrobenzeneacetate 

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.).

Enabling CO Insertion into o-Nitrostyrenes beyond Reduction for Selective Access to Indolin-2-one and Dihydroquinolin-2-one Derivatives

The transition metal-catalyzed reductive cyclization of o-nitrostyrene in the presence of carbon monoxide (CO) has been developed to be a general synthetic route to an indole skeleton, wherein CO was used as a reductant to deoxidize nitroarene into nitrosoarene and/or nitrene with CO2 release, but the selective insertion of CO into the heterocyclic product with higher atom economy has not yet been realized. Herein, the Pd-catalyzed reduction of o-nitrostyrene by CO and its regioselective insertion were efficiently achieved to produce synthetically useful five- and six-membered benzo-fused lactams. Detailed investigations revealed that the chemoselectivity to indole or lactam was sensitive to the nature of the counteranions of Pd2+ precursors, whereas ligands significantly decided the carbonylative regioselectivity by different reaction pathways. Using PdCl2/PPh3/B(OH)3 (condition A), an olefin hydrocarboxylation was primarily initiated followed by partial reduction of the NO2 moiety and cyclization reaction to give N-hydroxyl indolin-2-one, which was further catalytically reduced by CO to afford the indolin-2-one as the final product with up to 95% yield. When the reaction was conducted under the Pd(TFA)2/BINAP/TsOH·H2O system (condition B), complete deoxygenation and carbonylation of the NO2 group occurred initially to yield the corresponding isocyanate followed by internal hydrocyclization to generate 3,4-dihydroquinolin-2-one with up to 98% yield. Importantly, the methodology could be efficiently applied in the synthesis of marketed drug Aripiprazole.

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.

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.

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

Process of preparing nitrodihydroaryl carbonyl compounds

Nitroaryl carbonyl Formula (IIA) compounds, their nitrodihydroaryl carbonyl Formula (I) intermediates, processes for preparing Formula (II) compounds, and a process for preparing Formula (I) compounds, wherein each process comprises the reaction of a nitroaryl compound with a silane.

α-Nitroarylation of Ketones and Esters: An Exceptionally Facile Synthesis of Indoles, 2-Indolinones, and Arylacetic Acids

Silyl enol ethers and ketene silyl acetals add to aromatic nitro compounds in the presence of fluoride ion sources to give dihydroaromatic nitronates which are readily oxidized to α-nitroaryl carbonyl compounds by DDQ or Br2.These versatile intermediates are readily converted into indoles or 2-indolinones by reductive cyclization.Since halogen substituents on the aromatic ring are not displaced in the initial alkylation reaction, nucleophilic substitution of these groups, followed by functional group manipulations of the nitro group, permits easy access to indoles, 2-indolinones, and arylacetic acids with varied substitution patterns.