318-54-7

Usage

Uses

Used in Pharmaceutical Synthesis:
1-Methyl-3-(trifluoroacetyl)-1H-indole is used as an intermediate in the synthesis of pharmaceuticals for its ability to be modified to create a variety of different derivatives. The trifluoroacetyl group allows for the development of compounds with enhanced biological activity and selectivity, which can be crucial in drug discovery and medicinal chemistry.
Used in Organic Chemistry Research:
In the field of organic chemistry, 1-Methyl-3-(trifluoroacetyl)-1H-indole serves as a valuable compound for research purposes. Its reactivity and the presence of the trifluoroacetyl group make it an interesting subject for studying reaction mechanisms, exploring new synthetic routes, and understanding the influence of functional groups on molecular properties.
Used in Drug Development:
1-Methyl-3-(trifluoroacetyl)-1H-indole is utilized in drug development as a precursor to potentially active pharmaceutical ingredients. Its structural features can be optimized to target specific biological pathways or receptors, contributing to the creation of new therapeutic agents with improved efficacy and safety profiles.
Used in Chemical Synthesis Industry:
1-Methyl-3-(trifluoroacetyl)-1H-indole is employed in the chemical synthesis industry as a building block for the creation of complex organic molecules. Its versatility in undergoing various chemical transformations makes it a valuable component in the synthesis of specialty chemicals, agrochemicals, and other advanced materials.

InChI:InChI=1/C11H8F3NO/c1-15-6-8(10(16)11(12,13)14)7-4-2-3-5-9(7)15/h2-6H,1H3

Upstream product

• 603-76-9 1-methylindole 
• 108030-46-2 (E,E)-1-(N,N-dimethylamino)-4-nitro-1,3-butadiene 
• 76-05-1 trifluoroacetic acid 
• 407-25-0 trifluoroacetic anhydride 
• 6965-44-2 N-Methyl-indole-3-carbinol 
• 14618-45-2 2,2,2-trifluoro-1-(1H-indol-3-yl)ethanone 
• 1574373-47-9 (E)-2,2,2-trifluoro-1-(1-methyl-1H-indol-3-yl)ethanone oxime 
• 13081-18-0 ethyl-3,3,3-trifluoropyruvate 
• 116757-91-6 2,2,2-trifluoro-1-(1-methyl-1H-indol-3-yl)ethan-1-ol 
• 433-27-2 ethyl trifluoroacetaldehyde hemiacetal 
• 367-57-7 1,1,1-Trifluoro-2,4-pentanedione 
• 1522-22-1 1,1,1,5,5,5-hexafluoroacetylacetone 
• 120-72-9 indole 
• 31896-75-0 bis(1-methyl-1H-indol-3-yl)methane 

Downstream Products

• 116757-91-6 2,2,2-trifluoro-1-(1-methyl-1H-indol-3-yl)ethan-1-ol 
• 207619-48-5 (1-methyl-1H-indol-3-yl)(piperidin-1′-yl)methanone 
• 1032650-00-2 1-(4-fluorophenyl)-5-[2,2,2-trifluoro-1-hydroxy-1-(1-methyl-1H-indol-3-yl)ethyl]-1,3-dihydrobenzimidazol-2-one 
• 1032649-39-0 1-(4-fluorophenyl)-3-methyl-5-[2,2,2-trifluoro-1-hydroxy-1-(1-methyl-1H-indol-3-yl)ethyl]-1,3-dihydro-benzimidazol-2-one 
• 1032649-38-9 2,2,2-trifluoro-1-[1-(4-fluorophenyl)-2-methyl-1H-benzimidazol-5-yl]-1-(1-methyl-1H-indol-3-yl)ethanol 
• 1032649-93-6 2,2,2-trifluoro-1-[3-(4-fluorophenyl)imidazo[1,5-a]pyridin-7-yl]-1-(1-methyl-1H-indol-3-yl)ethanol 
• 1032649-37-8 2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-benzotriazol-5-yl]-1-(1-methyl-1H-indol-3-yl)ethanol 
• 126921-19-5 3-chlorocarbonyl-1-methylindole 
• 1417717-60-2 1,1,1-trifluoro-2-(1-methyl-1H-indol-3-yl)-4-phenylbut-3-yn-2-ol 

Relevant academic research and scientific papers

Acylation of activated aromatic substrates under mild conditions with (RCO)2O/Me2S/BF3

An efficient procedure for acylation and perfluoroacylation of activated aromatic substrates under mild conditions using the system (RCO)2O/Me2S/BF3 in CH2Cl2 is described. It is believed that dimethylacylsulfonium salts, RCOSMe2+RCO2BF3-, are the active acylating agents.

CONDENSATION REACTIONS OF A NITRODIENAMINE WITH INDOLES IN TRIFLUOROACETIC ACID

Treatment of a nitrodienamine (1) with indoles in trifluoroacetic acid gave condensation products.

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.

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.

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.

Efficient Synthesis and Biological Activity of Novel Indole Derivatives as VEGFR-2 Tyrosine Kinase Inhibitors

A series of novel indole derivatives were synthesized as potent inhibitors for the vascular endothelial growth factor receptor 2 (VEGFR-2) tyrosine kinase. Among those, compound 10b demonstrated the highest growth inhibition rate of 66.7% against the VEGFR-2 tyrosine kinase at 10 μM which indicates that indole-benzothiazole might be the favorable structure. The binding mode of compound 10b with VEGFR-2 tyrosine kinase was evaluated by molecular docking.

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.

Electronic Nature of Ketone Directing Group as a Key to Control C-2 vs C-4 Alkenylation of Indoles

A novel mode of achieving site selectivity between C-2 and C-4 positions in the indole framework by altering the property of the ketone directing group is disclosed. Methyl ketone, as directing group, furnishes exclusively C-2 alkenylated product, whereas trifluoromethyl ketone changes the selectivity to C-4, indicating that the electronic nature of the directing group controls the unusual choice between a 5-membered and a 6-membered metallacycle. The screening of other carbonyl-derived directing groups reveals that strong and weak directing groups exhibit opposite selectivity. Experimental controls and deuteration experiments lend support to the proposed mechanism.

Friedel-Crafts Fluoroacetylation of Indoles with Fluorinated Acetic Acids for the Synthesis of Fluoromethyl Indol-3-yl Ketones under Catalyst- and Additive-Free Conditions

A simple and efficient protocol for the fluoroacetylation of indoles is reported. The reaction uses fluorinated acetic acids as the fluoroacetylation reagents to synthesize diverse fluoromethyl indol-3-yl ketones in good yields under catalyst- and additive-free conditions. In addition, the only byproduct is water in this transformation. The synthetic utility of this reaction was also demonstrated by the concise synthesis of α-(trifluoromethyl)(indol-3-yl)methanol and indole-3-carboxylic acid.