25700-07-6

Usage

Uses

Used in Pharmaceutical Synthesis:
1-(4-Indol-1-yl-phenyl)-ethanone is used as a key intermediate in the synthesis of various organic molecules and pharmaceutical compounds. Its versatile chemical structure allows for the creation of complex organic molecules, making it an essential component in the development of new drugs and therapies.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 1-(4-Indol-1-yl-phenyl)-ethanone is used as a building block for the development of novel drug candidates. Its unique structure and properties enable researchers to explore its potential in targeting specific receptors and pathways, which could lead to the discovery of new treatments for various diseases.
Used in Drug Discovery Research:
1-(4-Indol-1-yl-phenyl)-ethanone plays a significant role in drug discovery research, where it is utilized to investigate its potential as a ligand for certain receptors. This research could contribute to the development of new drugs with improved efficacy and selectivity, ultimately benefiting patients in need of novel therapeutic options.
Used in Anticancer Research:
1-(4-Indol-1-yl-phenyl)-ethanone has been studied for its potential as an anticancer agent. Its chemical structure and properties make it a promising candidate for further research into its ability to target cancer cells and inhibit tumor growth, potentially leading to the development of new cancer treatments.

InChI:InChI=1/C16H13NO/c1-12(18)13-6-8-15(9-7-13)17-11-10-14-4-2-3-5-16(14)17/h2-11H,1H3

Upstream product

• 120-72-9 indole 
• 13329-40-3 4-Iodoacetophenone 
• 99-90-1 para-bromoacetophenone 
• 99-91-2 para-chloroacetophenone 
• 65185-58-2 2-(2-bromophenyl)ethanamine 
• 696-62-8 para-iodoanisole 
• 31823-10-6 tris(4-acetylphenyl) phosphate 

Relevant academic research and scientific papers

Palladium-Catalyzed Three-Component Regioselective Dehydrogenative Coupling of Indoles, 2-Methylbut-2-ene, and Carboxylic Acids

Five-carbon (C5) structural units are the fundamental building blocks of many natural products. An unprecedented palladium-catalyzed three-component dehydrogenative cascade coupling of indoles, 2-methylbut-2-ene, and carboxylic acids has been developed. The approach enables the straightforward introduction of a C3′-bonded five-carbon structural unit with a tertiary alcohol quaternary carbon center into indoles. The protocol employs 2-methylbut-2-ene as the C5 source and is featured by a broad substrate scope, atom and step economies, and high chemo- and regioselectivies.

Cobalt-Catalyzed C-H Activation and [3 + 2] Annulation with Allenes: Diastereoselective Synthesis of Indane Derivatives

An unprecedented bidentate directing-group-assisted cobalt-catalyzed oxidative C-H activation of aryl hydrazones followed by asyn-diastereoselective [3 + 2] annulation reaction has been achieved, employing allenes as the annulation partners. The selective 2,3-migratory insertion of allenes with arylcobalt(III) species and the subsequent intramolecular diastereoselective nucleophilic addition ofη1-allylcobalt onto the imine resulted in [3 + 2] annulation over the alternative [4 + 2] annulation. Furthermore, the oxidative annulation obviates the need for stoichiometric metal oxidants and proceeds under aerobic conditions.

A Pd/Cu-Free magnetic cobalt catalyst for C-N cross coupling reactions: synthesis of abemaciclib and fedratinib

Herein, the synthesis of a nano-catalytic system comprising magnetic nanoparticles as the core and edible natural ligands bearing functional groups as supports for cobalt species is described. Subsequent to its characterization, the efficiency of the catalyst was investigated for C-N cross-coupling reactions using assorted derivatives of amines and aryl halides. This novel and easily accessible Pd- and Cu-free catalyst exhibited good catalytic activity in these reactions using γ-valerolactone (GVL) at room temperature; good recyclability bodes well for the future application of this strategy. The introduced catalytic system is attractive in view of the excellent efficiency in an array of coupling reactions and its versatility is illustrated in the synthesis of abemaciclib and fedratinib, which are FDA-approved new and significant anti-cancer medicinal compounds that are prepared under green reaction conditions.

Ligand and Cu freeN-arylation of indoles, pyrroles and benzylamines with aryl halides catalyzed by a Pd nanocatalyst

Herein, theN-arylation of aromatic heterocycles like indoles and pyrroles is reported by a Pd nanocatalyst under ligand- and Cu-free conditions. The reaction conditions tolerate several functional groups and work very efficiently for aryl iodides and bromides. Aryl chlorides are also successful as the coupling partners albeit with lower yields. The methodology is also applicable for theN-arylation of aliphatic primary amines as demonstrated by the reactions of benzylamine with several aryl iodides as well as bromides. The recyclable Pd nanocatalyst catalyzes the reaction by a heterogeneous mechanism, which has been demonstrated by several techniques including the three phase test and thein situICP-MS analysis of the reaction mixture.

Nickel-catalyzed decarbonylation of: N -acylated N-heteroarenes

Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes is developed. This method can be used to produce a variety of N-aryl heteroarenes, including pyrroles, indoles, carbazoles and phenoxazines, using benzoic acid derivatives as arylating reagents. Arylnickelamide intermediates that are relevant to the catalytic reaction were characterized by X-ray crystallography. When N-acylated benzimidazoles are used as substrates, decarbonylation accompanied 1,2-migration to form 2-arylated benzimidazoles.

Palladium-catalyzed c(sp2)-n bond cross-coupling with triaryl phosphates

The first general palladium-catalyzed amination of aryl phosphates is described. The combination of MorDalPhos with [Pd(-cinnamyl)Cl]2 enables the amination of electron-rich, electron-neutral, and electron-poor aryl phosphates with a board range of aromatic, aliphatic, and heterocyclic amines. Common functional groups such as ether, keto, ester, and nitrile show an excellent compatibility in this reaction condition. The solvent-free amination reactions are also successful in both solid coupling partners. The gram-scale cross-coupling is achieved by this catalytic system.

Palladium-Catalyzed C(sp2)-N Bond Cross-Coupling with Triaryl Phosphates

The first general palladium-catalyzed amination of aryl phosphates is described. The combination of MorDalPhos with [Pd(?-cinnamyl)Cl]2 enables the amination of electron-rich, electron-neutral, and electron-poor aryl phosphates with a board range of aromatic, aliphatic, and heterocyclic amines. Common functional groups such as ether, keto, ester, and nitrile show an excellent compatibility in this reaction condition. The solvent-free amination reactions are also successful in both solid coupling partners. The gram-scale cross-coupling is achieved by this catalytic system.

A waste-minimized protocol for copper-catalyzed Ullmann-type reaction in a biomass derived furfuryl alcohol/water azeotrope

We report the use of biomass-derived furfuryl alcohol as an effective bidentate ligand able to promote the Ullmann-type copper-catalyzed coupling of aryl halides with heteroaromatic or aliphatic amines. Furfuryl alcohol (FA) can be mixed with water to form the corresponding azeotrope (20 wt% of FA) and therefore can be easily recovered and reused. This protocol is efficiently applied to substrates with various electronic nature and affords the expected products (27 examples) in generally good to excellent yields. It has also been demonstrated that the protocol is both chemically and environmentally effective as the azeotropic mixture can be easily and almost quantitatively recovered at the end of the process.

SBA-15-functionalized melamine-pyridine group-supported palladium(0) as an efficient heterogeneous and recyclable nanocatalyst for N-arylation of indoles through Ullmann-type coupling reactions

SBA-15-functionalized melamine-pyridine group-supported palladium(0) was found to serve as a heterogeneous and recyclable nanocatalyst for N-arylation of indoles with aryl iodides under a low catalyst loading (0.3mol% of Pd) through Ullmann-type C￡N coupling reactions. A variety of aryl iodides could be aminated to provide the N-arylated products in good to excellent yields without the need of an inert atmosphere. Also, this catalyst was found to be an efficient system for the N-arylation of other nitrogen-containing heterocycles with aryl iodides. The heterogeneous palladium catalyst could be recovered by simple filtration of the reaction solution and reused for six cycles without significant loss in its activity.

Palladium nanoparticles supported on modified single-walled carbon nanotubes: A heterogeneous and reusable catalyst in the Ullmann-type N-arylation of imidazoles and indoles

Air- and moisture-stable and recyclable palladium nanoparticles supported on modified single-walled carbon nanotubes (SWCNT-Met/Pd) behave as very efficient heterogeneous catalysts in the Ullmann coupling of imidazoles and indoles with aryl iodides to afford the corresponding C-N coupling reactions under aerobic conditions. These cross coupled products were produced in excellent yields at low palladium loading (～0.2 mol%) and the heterogeneous catalyst can be readily recovered by simple filtration and reused five times without a noticeable loss in its catalytic activity.