14618-45-2

Usage

Uses

Used in Pharmaceutical Chemistry:
3-(Trifluoroacetyl)indole is used as a reactant for the enantioselective synthesis of indoles via palladium-catalyzed kinetic asymmetrical alkylation. This application is significant for the development of chiral drugs with improved efficacy and reduced side effects.
Used in Organic Synthesis:
1. 3-(Trifluoroacetyl)indole is used as a reactant for the preparation of N-pyridinyl indolecarboxamides via amidation of aminopyridine derivatives with indolecarboxylic acid. This reaction is crucial for the synthesis of complex molecular structures with potential applications in various industries.
2. It is also used as a reactant for the preparation of mast cell tryptase inhibitors, starting from indoles. Amidation serves as the key step in this process, which is essential for the development of novel therapeutic agents targeting mast cell-related diseases.
3. Additionally, 3-(Trifluoroacetyl)indole is used as a reactant for the formation of Michael adducts via the Baylis-Hillman reaction. This reaction is an important tool in organic synthesis, allowing for the creation of new carbon-carbon bonds and the synthesis of various organic compounds.
4. Furthermore, it is used as a reactant for the preparation of indolecarboxamides via haloform cleavage of (trifluoroacetyl)indole with lithium dialkylamides. This reaction contributes to the synthesis of diverse indole-based compounds with potential applications in various fields.

InChI:InChI=1/C10H6F3NO/c11-10(12,13)9(15)7-5-14-8-4-2-1-3-6(7)8/h1-5,14H

Upstream product

• 120-72-9 indole 
• 353-85-5 trifluoroacetonitrile 
• 76-05-1 trifluoroacetic acid 
• 407-25-0 trifluoroacetic anhydride 
• 1477-50-5 Indole-2-carboxylic acid 
• 4442-11-9 lithium piperidide 
• 207619-47-4 N-benzenesulfonyl-3-trifluoroacetylindole 
• 354-32-5 trifluoracetyl chloride 
• 13081-18-0 ethyl-3,3,3-trifluoropyruvate 
• 116757-85-8 2,2,2-trifluoro-1-(indol-3-yl)ethanol 
• 433-27-2 ethyl trifluoroacetaldehyde hemiacetal 

Downstream Products

• 318-54-7 2,2,2-trifluoro-1-(1-methyl-1H-indol-3-yl)ethan-1-one 
• 771-50-6 1H-indole-3-carboxylic acid 
• 27393-78-8 1-(indole-3-carbonyl)-pyrrolidine 
• 207619-47-4 N-benzenesulfonyl-3-trifluoroacetylindole 
• 342885-53-4 2,2,2-trifluoro-1-(1-methanesulfonyl-1H-indol-3-yl)-ethanone 
• 626234-75-1 5-benzoyl-3-trifluoroacetylindole 
• 626234-76-2 5-(4'-methylbenzoyl)-3-trifluoroacetylindole 
• 1255172-39-4 (S)-2,2,2-trifluoro-1-(1-(1-((4-methoxybenzyl)amino)but-3-en-2-yl)-1H-indol-3-yl)ethanone 
• 1631028-53-9 2,2,2-trifluoro-1-(1-tosyl-1H-indol-3-yl)ethan-1-one 
• 1638653-37-8 C₁₈H₁₅F₃N₂O₅S 
• 256391-56-7 1-(1-benzyl-1H-indol-3-yl)-2,2,2-trifluoroethan-1-one 

Relevant academic research and scientific papers

Br?nsted Acid-Catalyzed Asymmetric Friedel-Crafts Alkylation of Indoles with Benzothiazole-Bearing Trifluoromethyl Ketone Hydrates

An efficient Br?nsted acid-catalyzed asymmetric Friedel-Crafts alkylation of indoles with benzothiazole-bearing trifluoromethyl ketone hydrates as electrophiles has been developed. The mild organocatalytic reactions proceeded well with low catalyst loading to afford a range of enantioenriched α-trifluoromethyl tertiary alcohols containing both benzothiazole and indole rings with excellent yields and enantioselectivities.

A new approach to the pyrrolo[3,4-b]indole ring system

We report an approach to the pyrrolo[3,4-b]indole ring system that involves a new synthesis of pyrrolo[3,4-b]indol-1(2H)ones, which are known precursors to pyrrolo[3,4-b]indoles. 3-Trifluoroacetylindole is prepared from indole and converted into indole carboxamides upon reaction with lithiated amines. Subsequent C-2 bromination followed by a tri-n-butyltin hydride induced 1,5-radical translocation and 5-endo-trig cyclization affords 3,4-dihydropyrrolo[3,4-b]indol-1(2H)-one which upon reduction with DIBAL by the method of Kreher gives pyrrolo[3,4-b]indole.

Palladium-Catalyzed 2-fold C-H Activation/C-C Coupling for C4-Arylation of Indoles Using Weak Chelation

Palladium-catalyzed weak chelation-assisted regioselective C4-arylation of indoles has been accomplished using a readily available arene at moderate temperature. The C4-arylation, weak chelating benzoyl (Bz) directing group, cross-dehydrogenative coupling (CDC), broad substrate scope, and late-stage diversifications are the important practical features.

Salicylaldehyde-Promoted Cobalt-Catalyzed C-H/N-H Annulation of Indolyl Amides with Alkynes: Direct Synthesis of a 5-HT3 Receptor Antagonist Analogue

A cobalt-catalyzed annulation of the C(sp2)-H/N-H bond of indoloamides with alkynes assisted by 8-aminoquinoline is reported for the synthesis of six-membered indololactams. The use of salicylaldehyde as the ligand is crucial for this transformation. The protocol has a broad scope for both alkynes and indoles. Preparing an active Co complex illustrates that salicylaldehyde plays a key role in the C-H activation step. The synthetic applications are proven by the gram-scale reaction and one-step construction of the multicyclic 5-HT3 receptor antagonist.

Discovery of a lead series of potent benzodiazepine 5-HT2C receptor agonists with high selectivity in functional and binding assays

A series of potential new 5-HT2 receptor scaffolds based on a simplification of the clinically studied, 5-HT2CR agonist vabicaserin, were designed. An in vivo feeding assay early in our screening process played an instrumental part in the lead identification process, leading us to focus on a 6,5,7-tricyclic scaffold. A subsequent early SAR investigation provided potent agonists of the 5-HT2C receptor that were highly selective in both functional and binding assays, had good rat PK properties and that significantly reduced acute food intake in the rat.

High-throughput screening of bioactive compounds via new catalytic reaction in the pooled mixture

To increase the chances of finding new candidate molecules with medicinal properties, while expending less resource and effort, the present study used pooled substrates as starting materials. A bisindole compound that showed inhibitory activity was then isolated from the mixture, and the activity was improved by optimizing the substituents on the indole skeleton.

Asymmetric Hydrogenation of Aryl Perfluoroalkyl Ketones Catalyzed by Rhodium(III) Monohydride Complexes Bearing Josiphos Ligands

The asymmetric hydrogenation of 2,2,2-trifluoroacetophenones and aryl perfluoroalkyl ketones was developed using a unique, well-defined chloride-bridged dinuclear rhodium(III) complex bearing Josiphos-type diphosphine ligands. These complexes were prepared from [RhCl(cod)]2, Josiphos ligands, and hydrochloric acid. As catalyst precursors, they allow for the efficient and enantioselective synthesis (up to 99 % ee) of chiral secondary alcohols with perfluoroalkyl groups. This system does not require an activating base for the hydrogenation of 2,2,2-trifluoroacetophenones. Additionally, the enantioselective C=O hydrogenations of 2-phenyl-3-(haloacetyl)-indoles, a class of privileged structures in medicinal chemistry, is reported for the first time.

Cell death inhibitor and novel compound

Provided is a cell-death inhibitor including, as an active ingredient thereof, a compound represented by formula (1), and/or a compound represented by formula (2). The cell-death inhibitor exhibits high cell-death inhibition activity.

Copper-mediated trifluoroacetylation of indoles with ethyl trifluoropyruvate

Direct trifluoroacetylation of indoles with ethyl trifluoropyruvate as a trifluoroacetylating reagent has been developed. This novel protocol provides an attractive route for the preparation of 3-trifluoroacetylindole derivatives, due to its operational simplicity and practicability as well as mild reaction conditions.

Synthesis method for 3-(trifluoroacetyl)indole derivative

The invention discloses a synthesis method for a 3-(trifluoroacetyl)indole derivative and belongs to the technical field of organic synthesis intermediates. The method particularly includes the following steps: 1) feeding dimethyl sulfoxide, an indole derivative, ethyl trifluoropyruvate and cuprous chloride into a pressure-resistant reaction tube, tightly screwing a plug of the reaction tube, and performing a magnetic-stirring reaction for 12 h in oil bath at 80 DEG C; 2) when the reaction is finished, performing extraction with ethyl ether and mixing organic phases, performing pressure reduced evaporation to remove most of the solvent, and performing column chromatography separation and purification to residual mixture liquid with petroleum ether and ethyl acetate, volume ratio being 5:1-10:1, as a leaching liquid, thereby producing the product. The 3-(trifluoroacetyl)indole derivative has wide applications in the fields such as medicines, pesticides, etc. The synthesis method is low in cost, has simple operations and high yield, and has excellent application prospect.