170489-16-4

Usage

Uses

Used in Organic Synthesis:
1,4-dimethyl-1H-indole-3-carbaldehyde is used as an intermediate in the production of various organic compounds, contributing to the synthesis of a range of chemical products due to its reactive functional groups.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,4-dimethyl-1H-indole-3-carbaldehyde is utilized as an intermediate for the synthesis of different pharmaceuticals, playing a crucial role in the development of new drugs.
Used in Agrochemical Development:
1,4-dimethyl-1H-indole-3-carbaldehyde is used as a precursor in the development of agrochemicals, where its chemical properties can be harnessed to create compounds that have applications in agriculture.
Used in Antioxidant Formulation:
1,4-dimethyl-1H-indole-3-carbaldehyde is also used in the formulation of antioxidants, where its chemical structure may contribute to the stabilization of other compounds and prevention of oxidative degradation.
Used in Biological Research:
1,4-dimethyl-1H-indole-3-carbaldehyde is used as a subject of biological research for its potential anti-inflammatory and antitumor properties, indicating its possible use in the development of therapeutic agents for various diseases.
Used in Anti-inflammatory Applications:
As an anti-inflammatory agent, 1,4-dimethyl-1H-indole-3-carbaldehyde is studied for its potential to modulate inflammatory responses, which could be beneficial in treating conditions characterized by inflammation.
Used in Antitumor Applications:
In the realm of antitumor research, 1,4-dimethyl-1H-indole-3-carbaldehyde is explored for its potential to inhibit tumor growth, making it a candidate for further investigation in oncology.

InChI:InChI=1/C11H11NO/c1-8-4-3-5-10-11(8)9(7-13)6-12(10)2/h3-7H,1-2H3

Upstream product

• 27816-52-0 1,4-dimethylindole 
• 75-50-3 trimethylamine 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 16096-32-5 4-methyl-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 4771-48-6 4-methyl-1H-indole-3-carboxaldehyde 
• 74-88-4 methyl iodide 
• 50-00-0 formaldehyd 

Relevant academic research and scientific papers

Cobalt-Catalyzed Enantioselective C–H Arylation of Indoles

Atropoisomeric (hetero)biaryls are scaffolds with increasing importance in the pharmaceutical and agrochemical industries. Although it is the most obvious disconnection to construct such compounds, the direct enantioselective C–H arylation through the concomitant induction of the chiral information remains extremely challenging and uncommon. Herein, the unprecedented earth-abundant 3d-metal-catalyzed atroposelective direct arylation is reported, furnishing rare atropoisomeric C2-arylated indoles. Kinetic studies and DFT computation revealed an uncommon mechanism for this asymmetric transformation, with the oxidative addition being the rate- and enantio-determining step. Excellent stereoselectivities were reached (up to 96% ee), while using an unusual N-heterocyclic carbene ligand bearing an essential remote substituent. Attractive dispersion interactions along with positive C–H-π interactions exerted by the ligand were identified as key factors to guarantee the excellent enantioselection.

Recyclable and reusablen-Bu4NBF4/PEG-400/H2O system for electrochemical C-3 formylation of indoles with Me3N as a carbonyl source

A safe, practical and eco-friendly electrochemical methodology for the synthesis of 3-formylated indoles has been developed by the utilization of Me3N as a novel formylating reagent. Stoichiometric oxidants, metal catalysts, and activating agents were avoided in this method, and an aqueous biphasic system ofn-Bu4NBF4/PEG-400/H2O was used as a recyclable and reusable reaction medium, which made this electrosynthesis approach more sustainable and environmentally friendly. This process expanded the substrate scope and functional group tolerance for bothN-EDG andN-EWG indoles. Furthermore, late-stage functionalization and total/formal synthesis of drugs and natural products were realized by means of this route.

Electrochemically Enabled C3-Formylation and -Acylation of Indoles with Aldehydes

Reported herein is an effective strategy for oxidative cross-coupling of indoles with various aldehydes. The strategy is based on a two-step transformation via a well-known Mannich-type reaction and a C-N bond cleavage for carbonyl introduction. The key step - the C-N bond cleavage of the Mannich product - was enabled by electrochemistry. This strategy (with over 40 examples) ensures excellent functional-group tolerance as well as late-stage functionalization of pharmaceutical molecules.

Access to Polycyclic Sulfonyl Indolines via Fe(II)-Catalyzed or UV-Driven Formal [2 + 2 + 1] Cyclization Reactions of N-((1H-indol-3-yl)methyl)propiolamides with NaHSO3

A variety of structurally novel polycyclic sulfonyl indolines have been synthesized via FeCl2-catalyzed or UV-driven intramolecular formal [2 + 2 + 1] dearomatizing cyclization reactions of N-(1H-indol-3-yl)methyl)propiolamides with NaHSO3 in an aqueous medium. The reactions involve the formation of one C-C bond and two C-S bonds in a single step.

Method for performing formylation reaction of indole compound by photocatalysis of carbazolyl-conjugated micro-porous polymers (CMPs)

The invention discloses a method for performing formylation reaction of an indole compound by photocatalysis of carbazolyl-conjugated micro-porous polymers (CMPs). The method is characterized in thatin an oxygen-containing atmosphere and water/organic mixed solvent system, the indole compound and a methylamine compound are subjected to formylation reaction under the catalytic action of iodized salt and CMPs and illumination conditions so as to obtain a 3-formaldehyde indole compound. The method has mild reaction conditions, can be implemented under room temperature and illumination conditionsand can be used for obtaining the target product in high selectivity and high yield, the reaction belongs to heterogeneous catalysis reaction, the catalyst can be recovered and recycled, and industrial production is facilitated.

Visible Light-Driven C-3 Functionalization of Indoles over Conjugated Microporous Polymers

Metal-free and heterogeneous organic photocatalysts provide an environmentally friendly alternative to traditional metal-based catalysts. This paper reports a series of carbazole-based conjugated microporous polymers (CMPs) with tunable redox potentials and explores their photocatalytic performance with regard to C-3 formylation and thiocyanation of indoles. Conjugated polymers were synthesized through FeCl3 mediated Friedel-Crafts reactions, and their redox potentials were well regulated by simply altering the nature of the core (i.e., 1,4-dibenzyl, 1,3,5-tribenzyl, or 1,3,5-triazin-2,4,6-triyl). The resulting CMPs exhibited high surface areas, visible light absorptions, and tunable semiconductor-range band gaps. With the highest oxidative capability, CMP-CSU6 derived from 1,3,5-tri(9H-carbazol-9-yl)benzene showed the highest efficiency for C-3 formylation and thiocyanation of indoles at room temperature. Notably, the as-made catalysts can be easily recovered with good retention of photocatalytic activity and reused at least five times, suggesting good recyclability. These results are significant for constructing high-performance porous polymer catalysts with tunable photoredox potentials targeting an efficient material design for catalysis.

CuCl2/TBHP-mediated direct chlorooxidation of indoles

CuCl2/TBHP-mediated direct chlorooxidation of indole derivatives under simple aerobic conditions was reported, leading to facile preparations of a range of 3,3-disubstituted 3-chlorooxindoles in good yields and selectivities.

Aerobic transition-metal-free visible-light photoredox indole C-3 formylation reaction

An aerobic visible-light-promoted indole C-3 formylation reaction catalyzed by Rose Bengal has been developed. This transition-metal-free process employs molecular oxygen as the terminal oxidant and uses TMEDA as the one-carbon source through C-N bond cleavage. The reaction is compatible with a variety of functional groups.

Benzimidazolone as potent chymase inhibitor: Modulation of reactive metabolite formation in the hydrophobic (P1) region

A new class of chymase inhibitor featuring a benzimidazolone core with an acid side chain and a P1 hydrophobic moiety is described. Incubation of the lead compound with GSH resulted in the formation of a GSH conjugate on the benzothiophene P1 moiety. Replacement of the benzothiophene with different heterocyclic systems such as indoles and benzoisothiazole is feasible. Among the P1 replacements, benzoisothiazole prevents the formation of GSH conjugate and an in silico analysis of oxidative potentials agreed with the experimental outcome.

1,2,3-Thiadiazole substituted pyrazolones as potent KDR/VEGFR-2 kinase inhibitors

KDR kinase inhibition is considered to play an important role in regulating angiogenesis, which is vital for the survival and proliferation of tumor cells. Recently we disclosed a structure-based kinase inhibitor design strategy which led to the identification of a new class of VEGFR-2/KDR kinase inhibitors bearing heterocyclic substituted pyrazolones as the core template. Instability in a rat S9 preparation and poor iv PK profiles for most of these inhibitors necessitated exploration of new pyrazolones to identify new analogs with improved metabolic stability. Optimization of the heterocyclic moiety led to the identification of the thiadiazole series of pyrazolones (D) as potent VEGFR-2/KDR kinase inhibitors. SAR modifications, kinase selectivity profiling, and structural elements for improved PK properties were explored. Oral bioavailability up to 29% was achieved in the rat. Modeling results based on the Glide XP docking approach supported our postulation regarding the interaction of the lactam segment of the pyrazolones with the hinge region of the KDR kinase.