934843-27-3

Usage

Class

Indole derivatives

Molecular weight

219.59 g/mol

Properties

Substituted indole with a chlorine atom and a trifluoromethyl group attached to the aromatic ring

Uses

Research and development, building block in the synthesis of pharmaceuticals, agrochemicals, and fine chemicals

Biological activities

May possess various biological activities

Importance

Important intermediate in organic synthesis

Handling

Handle with care due to hazardous properties

Upstream product

• 17422-33-2 6-chloroindole 
• 2926-29-6 Langlois reagent 
• 89-59-8 4-chloro-2-nitrotoluene 
• 2923-18-4 sodium 2,2,2-trifluoroacetate 
• 37585-16-3 (2-amino-4-chlorophenyl)methanol 
• 76-05-1 trifluoroacetic acid 
• 95-79-4 5-chloro-2-methyl-benzenamine 

Relevant academic research and scientific papers

An efficient approach to 2-CF3-indoles based on ortho-nitrobenzaldehydes

The catalytic olefination reaction of 2-nitrobenzaldehydes with CF3 CCl3 afforded stereose-lectively trifluoromethylated ortho-nitrostyrenes in up to 88% yield. The reaction of these alkenes with pyrrolidine permits preparation of α-CF3-β-(2-nitroaryl) enamines. Subsequent one pot reduction of nitro-group by Fe-AcOH-H2 O system initiated intramolecular cyclization to afford 2-CF3-indoles. Target products can be prepared in up to 85% yields. Broad synthetic scope of the reaction was shown as well as some followed up transformations of 2-CF3-indole.

Two-step, regioselective, multigram-scale synthesis of 2-(trifluoromethyl)indoles from 2-nitrotoluenes

The acylation of 2-nitrotoluenes using ethyl trifluoroacetate, one of the least expensive sources of a trifluoromethyl group, produces intermediate 2-nitrobenzyl trifluoromethyl ketones which, without the need for isolation, are cyclized under the action of Zn/AcOH providing 2-(trifluoromethyl)indoles unsubstituted at the C3 position. The developed method avoids the use of expensive catalysts and harsh reaction conditions. The method is readily scalable without a significant decrease in performance upon going from 10- to 250-mmol scale.

Au@ZnO Core-Shell: Scalable Photocatalytic Trifluoromethylation Using CF3CO2Na as an Inexpensive Reagent under Visible Light Irradiation

Trifluoromethylation is of significant importance for the synthesis of many small molecules vital for medicinal and agrochemical research. The importance of the CF3 group as well as the related synthetic challenges is so evident that many reagents have been reported for the synthesis of trifluoromethylated compounds, but these typical reagents are expensive and the methods for preparing them are difficult. Here, we report a new scalable and operationally simple trifluoromethylation reaction using sodium trifluoroacetate as a reagent and Au-modified ZnO as a photocatalyst under visible light irradiation. The reaction proceeds via trifluoromethylation of a broad range of aryl halides, arylboronic acids, and arene and heteroarene substrates. Some pharmaceutical and agrochemical compounds have been trifluoromethylated directly to demonstrate the applicability of the method.

Metal-free oxidative trifluoromethylation of indoles with CF3SO2Na on the C2 position

An efficient method of synthesizing 2-trifluoromethylindoles from indoles with easy-to-handle, cheap and low-toxic CF3SO2Na under metal-free conditions is described, which selectively introduces trifluoromethyl to indoles on the C2 position. The desired product can be obtained in 0.7 g yield. A radical intermediate may be involved in this transformation.

2-(Trifluoromethyl)indoles via Pd(0)-Catalyzed C(sp3)-H Functionalization of Trifluoroacetimidoyl Chlorides

Perfluoroalkylated indoles are valuable compounds in drug discovery. A Pd(0)-catalyzed C(sp3)-H functionalization enables access to 2-(trifluoromethyl)indoles from trifluoroacetimidoyl chlorides. These are stable compounds, easily obtained from

A New and Efficient One-Pot Synthesis of 2-Fluoroalkyl Substituted Indoles

A new simple and efficient one-pot synthesis of 2-fluoroalkyl substituted indoles from 2-aminobenzyl alcohols with fluorine-containing carboxylic acids in the presence of Ph3P, CCl4, and NEt3 is described. Various kinds of 2-fluoroalkyl substituted indole derivatives can be conveniently prepared.

Bromotriphenylphosphonium salt promoted one-pot cyclization to 2-fluoroalkyl-substituted indoles

2-Fluoroalkyl-substituted indoles were prepared in moderate to excellent yields through bromotriphenylphosphonium salt promoted ring formation with fluorine-containing carboxylic acids in the presence of triethylamine in toluene at reflux temperature. A range of 2-fluoroalkyl-substituted indole derivatives can be conveniently prepared.

Grignard cyclization reaction of fluorinated N-arylimidoyl chlorides: A novel and facile access to 2-fluoroalkyl indoles

2-Fluoroalkyl-substituted indole derivatives were simply prepared via the Grignard cyclization reaction (GCR) of corresponding fluorinated N-aryl imidoyl chlorides in good yields. This approach provides a novel and facile access to the biologically import

Fluorinated N-[2-(haloalkyl)phenyl]imidoyl chloride, a key intermediate for the synthesis of 2-fluoroalkyl substituted indole derivatives via Grignard cyclization process

Fluorinated N-[2-(haloalkyl)phenyl]imidoyl chloride, which was readily available from the corresponding anilines by using Uneyama's one-pot synthesis of fluorinated imidoyl chloride, was found to be a key intermediate for the facile synthesis of 2-fluoroa