614-96-0

Usage

Uses

Used in Pharmaceutical Industry:
5-Methylindole is used as a reactant for the preparation of pharmaceutically active 2-oxo-1-pyrrolidine analogues. These analogues have potential applications as anticancer agents, immunomodulators, and inhibitors of IL2-inducible T-cell kinase (ITK) and CRTh2 antagonists. The presence of the methyl group in 5-methylindole allows for the synthesis of these bioactive compounds, which can be further developed for therapeutic use.
Used in Medicinal Chemistry:
5-Methylindole is used in the synthesis of novel protein kinase inhibitors. Protein kinases are enzymes that play a crucial role in various cellular processes, including cell growth, differentiation, and apoptosis. Inhibition of specific protein kinases has been shown to have therapeutic potential in the treatment of various diseases, including cancer and inflammatory disorders. The use of 5-methylindole in the synthesis of these inhibitors can lead to the development of new drugs with improved efficacy and selectivity.

InChI:InChI=1/C9H9N/c1-7-2-3-9-8(6-7)4-5-10-9/h2-6,10H,1H3

Upstream product

• 3189-16-0 6-methyl-1,2,3,4-tetrahydroquinolin-3-ol 
• 872807-09-5 5-methyl-3-p-toluidino-indolin-2-one 
• 88-12-0 1-ethenyl-2-pyrrolidinone 
• 583-68-6 2-bromo-p-toluidine 
• 68742-28-9 5-ethyl-1H-indole 
• 15861-24-2 1H-indole-5-carbonitrile 
• 54397-16-9 2-phenyl-3-(4-methylphenyl)-oxo-1,3-thiazolidine 
• 61871-80-5 2-Amino-α-chlor-5-methylacetophenon 
• 3100-93-4 2,4-dimethylphenylisocyanide 
• 105896-42-2 N-(4-methylphenyl)ethenesulfinamide 
• 582319-44-6 2,2,2-Trifluoro-1-(5-methyl-indol-1-yl)-ethanone 
• 126759-40-8 2-<(5-methyl-2-nitrophenyl)methyl>-1,3-dioxane 
• 10241-97-1 5-methylindole-2-carboxylic acid 
• 180624-14-0 4-methyl-2-[2-(trimethylsilyl)ethynyl]aniline 

Downstream Products

• 52562-50-2 5-methylindole-3-carboxaldehyde 
• 10242-02-1 5-methyl-1H-indole-3-carboxylic acid 
• 30218-58-7 N,N-dimethyl-1-(5-methyl-1H-indol-3-yl)methanamine 
• 132659-95-1 2-(Benzhydrylidene-amino)-3-(5-methyl-1H-indol-3-yl)-propionic acid methyl ester 
• 142683-39-4 (2RS,3RS)-methyl N-(diphenylmethylene)-β-methyl-5-methyltryptophanate 
• 142683-39-4 (2SR,3RS)-methyl N-(diphenylmethylene)-β-methyl-5-methyltryptophanate 
• 126496-82-0 (S)-2-Benzyloxycarbonylamino-3-(5-methyl-1H-indol-3-yl)-propionic acid benzyl ester 
• 145303-51-1 (5-methyl-1H-indol-1-yl)(phenyl)methanone 
• 27816-53-1 1,5-dimethyl-1H-indole 
• 3484-35-3 5-methylindolin-2-one 
• 800366-84-1 3-(2'-methoxycarbonyl-2'-propenyl)-5-methylindole 
• 92554-52-4 5-methyl-3-(phenylsulfanyl)indole 
• 858515-93-2 2,2,2-trifluoro-1-(5-methyl-1H-indol-3-yl)-ethanone 
• 119229-73-1 5-methyl-1H-indol-1-amine 

Relevant academic research and scientific papers

Metal–Organic Layers Hierarchically Integrate Three Synergistic Active Sites for Tandem Catalysis

We report the design of a bifunctional metal–organic layer (MOL), Hf12-Ru-Co, composed of [Ru(DBB)(bpy)2]2+ [DBB-Ru, DBB=4,4′-di(4-benzoato)-2,2′-bipyridine; bpy=2,2′-bipyridine] connecting ligand as a photosensitizer and Co(dmgH)2(PPA)Cl (PPA-Co, dmgH=dimethylglyoxime; PPA=4-pyridinepropionic acid) on the Hf12 secondary building unit (SBU) as a hydrogen-transfer catalyst. Hf12-Ru-Co efficiently catalyzed acceptorless dehydrogenation of indolines and tetrahydroquinolines to afford indoles and quinolones. We extended this strategy to prepare Hf12-Ru-Co-OTf MOL with a [Ru(DBB)(bpy)2]2+ photosensitizer and Hf12 SBU capped with triflate as strong Lewis acids and PPA-Co as a hydrogen transfer catalyst. With three synergistic active sites, Hf12-Ru-Co-OTf competently catalyzed dehydrogenative tandem transformations of indolines with alkenes or aldehydes to afford 3-alkylindoles and bisindolylmethanes with turnover numbers of up to 500 and 460, respectively, illustrating the potential use of MOLs in constructing novel multifunctional heterogeneous catalysts.

Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations

Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.

Highly Ordered Mesoporous Cobalt Oxide as Heterogeneous Catalyst for Aerobic Oxidative Aromatization of N-Heterocycles

N-heterocycles are key structures for many pharmaceutical intermediates. The synthesis of such units normally is conducted under homogeneous catalytic conditions. Among all methods, aerobic oxidative aromatization is one of the most effective. However, in homogeneous conditions, catalysts are difficult to be recycled. Herein, we report a heterogeneous catalytic strategy with a mesoporous cobalt oxide as catalyst. The developed protocol shows a broad applicability for the synthesis of N-heterocycles (32 examples, up to 99 % yield), and the catalyst presents high turnover numbers (7.41) in the absence of any additives. Such a heterogenous approach can be easily scaled up. Furthermore, the catalyst can be recycled by simply filtration and be reused for at least six times without obvious deactivation. Comparative studies reveal that the high surface area of mesoporous cobalt oxide plays an important role on the catalytic reactivity. The outstanding recycling capacity makes the catalyst industrially practical and sustainable for the synthesis of diverse N-heterocycles.

Visible-light-mediated organoboron-catalysed metal-free dehydrogenation of N-heterocycles using molecular oxygen

The surge of photocatalytic transformation not only provides unprecedented synthetic methods, but also triggers the enthusiasm for more sustainable photocatalysts. On the other hand, oxygen is an ideal oxidant in terms of atom economy and environmental friendliness. However, the poor reactivity of oxygen at the ground state makes its utilization challenging. Herein, a visible-light-induced oxidative dehydrogenative process is disclosed, which uses an organoboron compound as the photocatalyst and molecular oxygen as the sole oxidant.Viathis approach, an array of N-heterocycles have been accessed under metal-free mild conditions, in good to excellent yields.

Iron-Catalyzed ?±,?-Dehydrogenation of Carbonyl Compounds

An iron-catalyzed α,β-dehydrogenation of carbonyl compounds was developed. A broad spectrum of carbonyls or analogues, such as aldehyde, ketone, lactone, lactam, amine, and alcohol, could be converted to their α,β-unsaturated counterparts in a simple one-step reaction with high yields.

Luminescent Platinum(II) Complexes with Bidentate Diacetylide Ligands: Structures, Photophysical Properties and Application Studies

A series of platinum(II) complexes supported by terphenyl diacetylide as well as diimine or bis-N-heterocyclic carbene (NHC) ligands have been prepared. The diacetylide ligands adopt a cis coordination mode featuring non-planar terphenyl moieties as revealed by X-ray crystallographic analyses. The electrochemical, photophysical and photochemical properties of these platinum(II) complexes have been investigated. These platinum(II) diimine complexes show broad emission with peak maxima from 566 nm to 706 nm, with two of them having emission quantum yields >60% and lifetimes 2 μs in solutions at room temperature, whereas the platinum(II) diacetylide complexes having bis-N-heterocyclic carbene instead of diimine ligand display photoluminescence with quantum yields of up to 28% in solutions and excited state lifetimes of up to 62 μs at room temperature. Application studies revealed that one of the complexes can catalyze photoinduced aerobic dehydrogenation of alcohols and alkenes, and a relatively non-toxic water-soluble Pt(II) complex displays anti-angiogenic activity.

Method for catalytically synthesizing indole derivative by using ferrous complex

The invention relates to a method for catalytically synthesizing an indole derivative by using a ferrous complex, which comprises the following step: by taking arylamine and acetaldehyde as raw materials and a ferrous complex containing a meta-carboboryl methylpyridine structure as a catalyst, conducting reacting at room temperature to prepare the indole derivative. Compared with the prior art, the method utilizes the ferrous complex to efficiently catalyze the reaction of arylamine and acetaldehyde at room temperature to prepare the indole derivative, the reaction condition is mild, the substrate range is wide, and the method has high catalytic activity and yield.

Aerobic Dehydrogenation of N-Heterocycles with Grubbs Catalyst: Its Application to Assisted-Tandem Catalysis to Construct N-Containing Fused Heteroarenes

An aerobic dehydrogenation of nitrogen-containing heterocycles catalyzed by Grubbs catalyst is developed. The reaction is applicable to various nitrogen-containing heterocycles. The exceptionally high functional group compatibility of this method was confirmed by the oxidation of an unprotected dihydroindolactam V to indolactam V. Furthermore, by taking advantage of the oxygen-mediated structural change of the Grubbs catalyst, we integrated ring-closing metathesis and subsequent aerobic dehydrogenation to develop the novel assisted-tandem catalysis using molecular oxygen as a chemical trigger. The utility of the assisted-tandem catalysis was demonstrated by the concise synthesis of N-containing fused heteroarenes including a natural antibiotic, pyocyanine.

Dehydrogenation and α-functionalization of secondary amines by visible-light-mediated catalysis

A visible-light-mediated process for dehydrogenation of amines has been described. The given protocol showed a broad substrate scope, mild reaction conditions and excellent results without the requirement of tedious purification. This process can be applied in one-pot functionalization of secondary amines with various nucleophiles through the cooperation of visible-light and Lewis acid catalysis, leading to the structurally varied essential components of biologically active molecules. In addition, Stern-Volmer studies and quenching experiments revealed the role of a catalyst and led to the proposed mechanism of this transformation.

Monoamine Oxidase (MAO-N) Biocatalyzed Synthesis of Indoles from Indolines Prepared via Photocatalytic Cyclization/Arylative Dearomatization

The biocatalytic aromatization of indolines into indole derivatives exploiting monoamine oxidase (MAO-N) enzymes is presented. Indoline substrates were prepared via photocatalytic cyclization of arylaniline precursors or via arylative dearomatization of unsubstituted indoles and in turn chemoselectively aromatized by the MAO-N D11 whole cell biocatalyst. Computational docking studies of the indoline substrates in the MAO-N D11 catalytic site allowed for the rationalization of the biocatalytic mechanism and experimental results of the biotransformation. This methodology represents an efficient example of biocatalytic synthesis of indole derivatives and offers a facile approach to access these aromatic heterocycles under mild reaction conditions.