825-70-7

Usage

Uses

Used in Pharmaceutical Industry:
5-Fluoro-2,3-dihydro-2-Methyl-1H-Indole is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure and fluorine atom may contribute to the development of new drugs with improved pharmacological properties, such as enhanced bioavailability, selectivity, and potency.
Used in Agrochemical Industry:
In the agrochemical industry, 5-Fluoro-2,3-dihydro-2-Methyl-1H-Indole may be utilized as a building block for the creation of novel agrochemicals, including pesticides and herbicides. Its specific chemical properties could potentially enhance the effectiveness and selectivity of these compounds, leading to more efficient and environmentally friendly agricultural practices.
Used in Materials Science:
5-Fluoro-2,3-dihydro-2-Methyl-1H-Indole may also find applications in the field of materials science, where its unique structure and properties could be employed in the development of new materials with specific characteristics. These materials could have potential uses in various industries, such as electronics, coatings, or advanced materials for specific applications.

Upstream product

• 83164-79-8 N-allyl-4-fluoroaniline 
• 399-72-4 5-fluoro-2-methyl-1H-indole 
• 371-40-4 4-fluoroaniline 
• 267002-55-1 2-allyl-4-fluorophenylamine 

Relevant academic research and scientific papers

METHOD FOR PRODUCING OPTICALLY ACTIVE COMPOUND, AND NOVEL METAL-DIAMINE COMPLEX

The present invention pertains to a method for producing an optically active compound which includes a step for reducing an imino group of an imine compound or a step for reducing an unsaturated bond of a heterocyclic compound, while in the presence of hydrogen gas as a hydrogen donor and one or more types of complexes selected from a group consisting of a complex represented by general formula (1), a complex represented by general formula (2), a complex represented by general formula (3), and a complex represented by general formula (4) (the general formulas (1)-(4) are as stipulated by claim 1).

Homogenous Pd-catalyzed asymmetric hydrogenation of unprotected indoles: Scope and mechanistic studies

An efficient palladium-catalyzed asymmetric hydrogenation of a variety of unprotected indoles has been developed that gives up to 98% ee using a strong Br?nsted acid as the activator. This methodology was applied in the facile synthesis of biologically active products containing a chiral indoline skeleton. The mechanism of Pd-catalyzed asymmetric hydrogenation was investigated as well. Isotope-labeling reactions and ESI-HRMS proved that an iminium salt formed by protonation of the C=C bond of indoles was the significant intermediate in this reaction. The important proposed active catalytic Pd-H species was observed with 1H NMR spectroscopy. It was found that proton exchange between the Pd-H active species and solvent trifluoroethanol (TFE) did not occur, although this proton exchange had been previously observed between metal hydrides and alcoholic solvents. Density functional theory calculations were also carried out to give further insight into the mechanism of Pd-catalyzed asymmetric hydrogenation of indoles. This combination of experimental and theoretical studies suggests that Pd-catalyzed hydrogenation goes through a stepwise outer-sphere and ionic hydrogenation mechanism. The activation of hydrogen gas is a heterolytic process assisted by trifluoroacetate of Pd complex via a six-membered-ring transition state. The reaction proceeds well in polar solvent TFE owing to its ability to stabilize the ionic intermediates in the Pd-H generation step. The strong Br?nsted acid activator can remarkably decrease the energy barrier for both Pd-H generation and hydrogenation. The high enantioselectivity arises from a hydrogen-bonding interaction between N-H of the iminium salt and oxygen of the coordinated trifluoroacetate in the eight-membered-ring transition state for hydride transfer, while the active chiral Pd complex is a typical bifunctional catalyst, effecting both the hydrogenation and hydrogen-bonding interaction between the iminium salt and the coordinated trifluoroacetate of Pd complex. Notably, the Pd-catalyzed asymmetric hydrogenation is relatively tolerant to oxygen, acid, and water.

NOVEL PYRIMIDINE DERIVATIVES, PREPARATION THEREOF, AND PHARMACEUTICAL USE THEREOF AS AKT(PKB) PHOSPHORYLATION INHIBITORS

The present invention relates to novel chemical compounds derived from pyrimidines, to the method for preparing same, to the novel intermediates obtained, to the use thereof as drugs, to the pharmaceutical compositions containing same, and to the therapeutic use thereof as AKT inhibitors.

NOVEL RHO KINASE INHIBITORS AND METHODS OF USE

The subject invention concerns materials and methods for treating diseases and disorders associated with expression of Rho associated kinases (ROCKs). Examples of diseases and disorders contemplated within the scope of the invention include, but are not limited to, oncological disorders, cardiovascular diseases, CNS disorders, and inflammatory disorders. In one embodiment, a method of the invention comprises administering a therapeutically effective amount of one or more compounds of the present invention, or a composition comprising the compounds, to a person or animal in need of treatment. The subject invention also concerns compounds that inhibit ROCKs, and compositions that comprise the inhibitor compounds of the invention. Compounds contemplated within the scope of the invention include, but are not limited to, those compounds shown in Table (5).

Chemoenzymatic preparation of optically active secondary amines: a new efficient route to enantiomerically pure indolines

An efficient chemoenzymatic route for the synthesis of optically active substituted indolines has been developed. Different lipases have been tested in the alkoxycarbonylation of these secondary amines, Candida antarctica lipase A (CAL-A) was found to be the best biocatalyst for 2-substituted-indolines, and C. antarctica lipase B (CAL-B) for 3-methylindoline. The combination of lipases with a variety of allyl carbonates and tert-butyl methyl ether (TBME) as solvent has allowed the isolation of the carbamate and amine derivatives with a high level of enantiopurity.

Novel strategies for the solid phase synthesis of substituted indolines and indoles

Using a polymer-bound selenenyl bromide resin, o-allyl and o-prenyl anilines were cycloaded to afford a series of solid-supported indoline and indole scaffolds. These scaffolds were then functionalized and cleaved via four distinct methods, namely traceless reduction, radical cyclization, radical rearrangement, and oxidative elimination, to afford 2-methyl indolines, polycyclic indolines, 2-methyl indoles, and 2-propenyl indolines, respectively. A number of small combinatorial libraries of compounds reminiscent of certain designed ligands of biological interest were constructed demonstrating the potential utility of the developed methodology to chemical biology studies and the drug discovery process.

Zn2+ montmorillonite catalyzed 3-aza-Cope rearrangement under microwave irradiation

N-Allylanilines undergo 3-aza-Cope rearrangement in the presence of Zn2+ montmorillonite under microwave irradiation in the absence of solvent to afford indoline derivatives in high yields. Similarly arylallyl thioethers are rearranged to dihydrobenzothiophenes.