21296-93-5

Usage

Uses

Used in Pharmaceutical Industry:
5-CHLORO-2,3-DIMETHYL-1H-INDOLE is used as a key intermediate in the synthesis of various pharmaceuticals for its diverse biological activities, including anticancer, antimicrobial, and antioxidant properties. Its unique structure allows for the development of new drugs with potential therapeutic benefits.
Used in Agrochemical Industry:
In the agrochemical industry, 5-CHLORO-2,3-DIMETHYL-1H-INDOLE is utilized as a building block for the creation of novel agrochemicals, such as pesticides and herbicides, due to its antimicrobial properties. This helps in the development of more effective and targeted solutions for agricultural challenges.
Used in Research Chemicals:
5-CHLORO-2,3-DIMETHYL-1H-INDOLE serves as a valuable research chemical, enabling scientists to study its properties and explore its potential applications in various fields. Its unique structure and biological activities make it an interesting subject for research and development.
Used in Drug Development:
5-CHLORO-2,3-DIMETHYL-1H-INDOLE has potential applications in the development of new drugs, particularly in the areas of oncology, infectious diseases, and oxidative stress-related conditions. Its diverse biological activities make it a promising candidate for further investigation and development into effective therapeutic agents.
Used in Organic Synthesis:
As a valuable intermediate in organic synthesis, 5-CHLORO-2,3-DIMETHYL-1H-INDOLE plays a crucial role in the synthesis of complex organic compounds. Its unique structure allows for the creation of a wide range of chemical entities, contributing to the advancement of organic chemistry and the development of new materials and compounds.

Upstream product

• 90875-41-5 Butyraldehyd-(p-chlor-phenylhydrazon) 
• 4812-23-1 2-nitro-but-2-ene 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 1075-35-0 5-chloro-2-methylindole 
• 106-47-8 4-chloro-aniline 
• 107-87-9 2-Pentanone 
• 124-38-9 carbon dioxide 
• 78-93-3 butanone 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 2028-63-9 but-3-yn-2-ol 
• 513-85-9 2.3-butanediol 

Downstream Products

• 1370410-18-6 (5-chloro-2,3-dimethyl-1H-indol-1-yl)(2-iodophenyl)methanone 
• 877178-50-2 3-benzyl-5-chloro-2,3-dimethyl-3H-indole 

Relevant academic research and scientific papers

Dearomatization of Indoles via Palladium-Catalyzed Allylic C-H Activation

The first Pd-catalyzed allylic dearomatization of substituted indoles triggered by C-H bond activation is reported. The presence of a catalytic amount of 2,5-DMBQ is proven to be a key factor for the high yield. This one-pot tandem allylic C-H activation/dearomatization sequence provides a straightforward access to 3,3-disubstituted indolines.

Fe-Catalyzed Sequential C(sp3)-H/N-H Annulation of 2-Methylindoles with Ethyl Trifluoropyruvate at Room Temperature: Construction of Pyrrolo[1,2-α]indoles

An efficient and benign iron-catalyzed room-temperature method was developed for direct sequential C(sp3)-H/N-H annulation to construct pyrroloindole scaffolds. This strategy features cheap and readily available raw materials and mild room-temperature reaction conditions and provides a green and practical method for the one-pot rapid synthesis of a wide range of diversely functionalized pyrrolo[1,2-α]indoles.

Synthesis and evaluation of aryl substituted propyl piperazines for potential atypical antipsychotic activity

Background: Schizophrenia is a disorder with complex etiology with hyperdopaminer-gia as the leading underlying cause. Atypical antipsychotics are the agents which do not give rise to significant extrapyramidal side effects and are more effective against negative symptoms of schizophrenia. Introduction: A new series of chloro-substituted substituted aryloxypiperazine derivatives and their indole based derivatives was designed and evaluated for atypical antipsychotic activity based on established models for combined dopaminergic and serotonergic antagonism. Method: The present series of compounds were designed based on 3D similarity studies, synthesized and evaluated for atypical antipsychotic activity in animal models for combined dopaminer-gic and serotonergic antagonism. The blood-brain barrier penetration potential was assessed from theoretical log BB values computed through an online software program. Results: Theoretical ADME profiling of the designed compounds based on selected physicochem-ical parameters suggested excellent compliance with Lipinski’s rules. The log BB values obtained for the compounds suggested a good potential for brain permeation. Indole substitution contributed towards an improved efficacy over aryloxy analogs. Lead compounds showed a potential for combined dopaminergic and serotonergic antagonism. Conclusion: The 5-methoxy indole based compounds 16 and 17 were identified as the lead compounds displaying a potential atypical antipsychotic profile.

Palladium-catalyzed dearomative allylation of indoles with cyclopropyl acetylenes: access to indolenine derivatives

A palladium-catalyzed redox-neutral allylic alkylation of indoles with cyclopropyl acetylenes has been disclosed. Various 1,3-diene indolenine framework bearing a quaternary stereocenter at the C3 position were synthesized straightforwardly in good to excellent yields with high regio- and stereoselectivities. The reaction could be further expanded to the dearomatization of naphthols to synthesize functionalized cyclohexadienones with 1,3-diene motifs. The reaction exhibited high atom economy and good functional group tolerance.

Allylic and Allenylic Dearomatization of Indoles Promoted by Graphene Oxide by Covalent Grafting Activation Mode

The site-selective allylative and allenylative dearomatization of indoles with alcohols was performed under carbocatalytic regime in the presence of graphene oxide (GO, 10 wt percent loading) as the promoter. Metal-free conditions, absence of stoichiometric additive, environmentally friendly conditions (H2O/CH3CN, 55 °C, 6 h), broad substrate scope (33 examples, yield up to 92 percent) and excellent site- and stereoselectivity characterize the present methodology. Moreover, a covalent activation model exerted by GO functionalities was corroborated by spectroscopic, experimental and computational evidences. Recovering and regeneration of the GO catalyst through simple acidic treatment was also documented.

1,3,4,9-TETRAHYDRO-2H-PYRIDO[3,4-B]INDOLE DERIVATIVE COMPOUNDS AND USES THEREOF

The present invention relates to 1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole derivative compounds and uses thereof. In particular, compounds of the invention have antibacterial activity and/or are capable of re-sensitizing methicillin-resistant Staphylococcus aureus to a P-lactam antibiotic or a combination of a P-lactam antibiotic and a P-lactamase inhibitor. The present invention also relates to a method for producing and using said compounds.

Palladium-Catalyzed Amination/Dearomatization Reaction of Indoles and Benzofurans

This report describes a palladium-catalyzed dearomatization and amination tandem reaction of 2,3-disubstituted indoles and benzofurans via the Catellani strategy. This reaction provides a new method for the construction of amino-substituted indoline-fused cyclic and benzofuran spiro compounds in good yields. The reaction has broad functional group compatibility and substrate scope.

B(C6F5)3-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles

The direct C3 alkylation of indoles and oxindoles is a challenging transformation, and only a few direct methods exist. Utilizing the underexplored ability of triaryl boranes to mediate the heterolytic cleavage of α-nitrogen C-H bonds in amines, we have developed a catalytic approach for the direct C3 alkylation of a wide range of indoles and oxindoles using amine-based alkylating agents. We also employed this borane-catalyzed strategy in an alkylation-ring opening cascade.

Synthesis and evaluation of indole derivatives as photosynthesis and plant growth inhibitors

Indole derivatives were synthetized based on the Fischer indole methodology using different phenyl hydrazine hydrochlorides and either cyclohexanone or 2-butanone. The pre- and post-emergent herbicidal activities were evaluated against Ipomoea grandifolia. A carbazole, 6-chloro-2,3,4,9-tetrahydro-1H-carbazole (3b), decreased the PIabs parameter by 32% and increased the cross-section related parameters, indicating the inactivation of the reaction center on photosystem II. Compound 3b acts as a post-emergent herbicide prototype since dry biomass was reduced by 50%, corroborating the fluorescence results. Comparing instead with a germination experiment, 2,3,4,9-tetrahydro-1H-carbazole (3a) was found to be the most effective agent, inhibiting seed germination by 22% and decreasing root length by 50%. The tetrahydrocarbazoles showed better results than indole derivatives potentially due to the presence of methylene groups at structures, which increase the compounds' lipophilicity and may facilitate their access to the plant. In addition, electron withdrawing groups on the aromatic ring were found to correlate with increased herbicide activity. Further optimization of this series towards the development of herbicides is ongoing.

Palladium-Catalyzed Dearomative Allylic Alkylation of Indoles with Alkynes to Synthesize Indolenines with C3-Quarternary Centers

A palladium-catalyzed dearomative allylic alkylation of indoles with alkynes to construct indolenines with C3-quarternary centers was reported. The in situ formed arylallene intermediate omitted the need to install leaving groups on the allylic compounds and employ extra oxidants to oxidize the allylic C-H bonds. The reaction exhibited good functional group tolerance and high atom economy. Moreover, the reaction was further expanded to synthesize pyrroloindolines and furanoindolines.