59050-37-2

Usage

Uses

Used in Pharmaceutical and Medicinal Chemistry:
2,2,2-Trifluoro-1-(2-phenyl-1H-indol-3-yl)ethan-1-one is used as a building block for the synthesis of various organic compounds due to its structural similarity to other biologically active molecules. Its unique trifluoromethyl group and aromatic moieties contribute to its potential applications in drug discovery and development.
Used in Drug Discovery and Development:
In the pharmaceutical industry, 2,2,2-trifluoro-1-(2-phenyl-1H-indol-3-yl)ethan-1-one is used as a precursor for the development of new drugs. Its structural features and chemical reactivity make it a promising candidate for the design and synthesis of novel therapeutic agents with potential applications in treating various diseases and medical conditions.
Used in Organic Synthesis:
2,2,2-Trifluoro-1-(2-phenyl-1H-indol-3-yl)ethan-1-one is used as a key intermediate in the synthesis of complex organic molecules. Its trifluoromethyl ketone functional group and aromatic moieties provide opportunities for further chemical modifications and functionalization, making it a valuable component in the preparation of advanced organic materials and specialty chemicals.

Upstream product

• 948-65-2 2-phenyl-indole 
• 407-25-0 trifluoroacetic anhydride 

Downstream Products

• 948-65-2 2-phenyl-indole 
• 927802-01-5 2-hydroxy-1-(2-phenyl-1H-indol-3-yl)ethanone 
• 412022-79-8 2-chloro-1-(2-phenyl-1H-indol-3-yl)ethanone 
• 1007982-22-0 2-oxo-2-(2-phenyl-1H-indol-3-yl)ethyl acetate 
• 1428443-61-1 2-azido-1-(2-phenyl-1H-indol-3-yl)-ethanone 
• 1428443-67-7 2-(4-phenyl-1H-1,2,3-triazol-1-yl)-1-(2-phenyl-1H-indol-3-yl)ethanone 
• 1428443-69-9 2-(methylamino)-N-((1-(2-oxo-2-(2-phenyl-1H-indol-3-yl)ethyl)-1H-1,2,3-triazol-4-yl)methyl)acetamide 
• 1428443-62-2 2-amino-1-(2-phenyl-1H-indol-3-yl)-ethanone 
• 1428443-70-2 tert-butyl N-methyl-N-(2-oxo-2-((2-oxo-2-(2-phenyl-1H-indol-3-yl)ethyl)amino)ethyl)carbamate 
• 1428443-71-3 3-amino-N-(2-oxo-2-(2-phenyl-1H-indol-3-yl)ethyl)pyrazine-2-carboxamide 
• 950034-18-1 2-(methyl(2-morpholino-2-oxoethyl)amino)-1-(2-phenyl-1H-indol-3-yl)ethan-1-one 
• 1428443-72-4 methyl 2-(methyl(2-oxo-2-(2-phenyl-1H-indol-3-yl)ethyl)amino)acetate 
• 1428443-73-5 2-(methyl(2-oxo-2-(2-phenyl-1H-indol-3-yl)ethyl)amino)-N-(prop-2-yn-1-yl)acetamide 
• 1428443-63-3 C₂₃H₁₉NO₂ 

Relevant academic research and scientific papers

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.

3-Substituted 2-phenyl-indoles: Privileged structures for medicinal chemistry

Privileged structures have been used in drug discovery targeting G protein-coupled receptors (GPCR) and other protein classes for more than 20 years. Their rich activity profiles and drug-like characteristics lend themselves to increased productivity in hit identification and lead optimisation. Recently we discovered two allosteric modulators 1 and 2 for the G protein-coupled receptor GPRC6A incorporating the privileged 2-phenyl-indole scaffold, functionalised at the 3-position. In order to develop new potential GPRC6A ligands we engaged in the development of synthetic routes to provide 2-phenyl-indoles with a variety of substituents at the indole 3-position. Herein we describe the development of optimised and efficient synthetic routes to a series of new 2-phenyl-indole building blocks 3 to 9 and show that these can be used to generate a broad variety of 3-substituted 2-phenyl-indoles of interest to medicinal chemists.