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• 2926-29-6 Langlois reagent 

Relevant academic research and scientific papers

Transition-metal- and phosphorus-free electrophilic trifluoromethylthiolation of indoles with sodium trifluoromethanesulfinates in ionic liquids

An acid-promoted protocol has been developed to achieve the transition-metal- and phosphorus-free electrophilic trifluoromethylthiolation of indoles using sodium trifluoromethanesulfinates in an imidazolium-based ionic liquid ([Hmim]Br). [Hmim]Br not only acts as a recyclable solvent, but also as the reductant in this transformation. The advantages of this chemistry include simple operation, use of a recyclable solvent, avoidance of transition-metal and phosphorus, and gram-scale synthesis.

AMINOPYRIMIDINE COMPOUNDS, PREPARATION METHODS AND USES THEREOF

Provided herein are novel compounds, for example, compounds having a Formula (I) or Formula (II), or a pharmaceutically acceptable salt thereof. Also provided herein are methods of preparing the compounds and methods of using the compounds, for example, for treating various cancer described herein, such as lung cancer (e.g., non-small cell lung cancer).

TfNHNHBoc as a SCF3 source for the sulfenylation of indoles

An unprecedented use of trifluoromethanesulfonyl hydrazides as effective SCF3 sources has been established in the sulfenylation of indoles. A range of substituted indoles participated in CuCl-catalyzed oxidative sulfenylation reaction with TfNHNHBoc in the presence of dimethyl sulfoxide to furnish structurally diverse 3-indolyl trifluoromethyl thioethers in moderate to good yields with very high regioselectivity.

Method for synthesizing trifluoromethyl sulfidethioetherified indole derivatives

The invention discloses a method for synthesizing trifluoromethyl sulfidethioetherified indole derivatives. The method comprises the steps of: performing reaction of sodium trifluoromethylsulfinate with indole derivatives in a solvent in which phosphorus trichloride is uniformly distributed with phosphorus trichloride, wherein the reaction temperature is 60 DEG C and the reaction time is 0.33-10 hours. The mole ratio of sodium trifluoromethylsulfinate to the indole derivatives to phosphorus trichloride is (7.5-5):5:(7.5-5). The raw materials for the synthesis method provided by the invention is cheap and easy to be obtained. The trifluoromethyl sulfidethioetherification reagent used is sodium trifluoromethylsulfinate which is stable in chemical properties, cheap and easy to be obtained.

Green indole compound vulcanization method with triphosgene as reducing agent

The invention discloses a green indole compound vulcanization method with triphosgene as a reducing agent. The method comprises the following steps: by taking indole and a derivative thereof as substrate, fluomethane sodium methanesulfinate, methyl sodium methanesulfinate, cyclopropyl sodium methanesulfinate or aryl sodium methanesulfinate as a vulcanization agent, triphosgene as a reducing agent,and acetonitrile as a solvent, stirring for 2 hours in an ice bath, carrying out TLC (Thin Layer Chromatography) reaction tracking, and after sufficient reactions are completed, carrying out column chromatography isolation, so as to obtain various indole vulcanization compounds. By adopting the method disclosed by the invention, the triphosgene is adopted as the reaction reducing agent, thiophenol and dithioether with serious smell is avoided, an expensive electrophilic trifluoromethyl sulfide reagent is avoided, and a phosphorous reducing agent which can do harm to the environment can be also avoided. Till now, the indole vulcanization method is not reported yet, the preparation method is simple and convenient, low in cost and high in yield, products can be directly prepared without anytransition metal catalyst or aid, and very high practical popularization values can be achieved.

Metal-Free Difluoromethylthiolation, Trifluoromethylthiolation, and Perfluoroalkylthiolation with Sodium Difluoromethane- sulfinate, Sodium Trifluoromethanesulfinate or Sodium Perfluoro- alkanesulfinate

A method for direct difluoromethylthiolation of Ar?H bonds is introduced. The stable and easy-to-handle HCF2SO2Na is reduced with (EtO)2P(O)H in the presence of TMSCl to generate HCF2S+ for the regioselective difluoromethylthiolation of aromatic compounds including indoles, pyrroles, and activated benzenes. This method is also applicable for the trifluoromethylthiolation with CF3SO2Na and the perfluoroalkylthiolation with RfSO2Na of arenes and heteroarenes. Reaction mechanisms associated with the metal-free electrophilic fluoroalkylthiolation reactions are also discussed. (Figure presented.).

Transition-metal-free direct trifluoromethylthiolation of electron-rich aromatics using CF3SO2Na in the presence of PhPCl2

A novel transition metal-free route for the direct trifluoromethylthiolation of electron-rich aromatics using CF3SO2Na in the presence of PhPCl2 was developed. More specifically, PhPCl2 was used as both a reducing and a chlorinating reagent for the first time in this CF3SO2Na-based trifluoromethylthiolation reaction. The absence of transition metals and the use of cheap and readily available reagents render this method an alternative and practical strategy for the trifluoromethylthiolation of electron-rich aromatics.

Transition-Metal-Free Direct Trifluoromethylthiolation and Trifluoromethylsulfoxidation of Electron-Rich Aromatics with CF3SO2Na in the Presence of PCl3

A new transition-metal-free route for the direct trifluoromethylthiolation and trifluoromethylsulfoxidation of electron-rich aromatics with CF3SO2Na in the presence of PCl3 was developed. Notably, PCl3 was used as a reducing and chlorination reagent. The transition-metal-free protocol utilized cheap and readily available reagents and exhibited good atom economy; therefore, it will serve as an alternative and practical strategy for the trifluoromethylthiolation and trifluoromethylsulfoxidation of electron-rich aromatics.

Selective Trifluoromethylthiolation and Trifluoromethylsulfinylation of Indoles with Sodium Trifluoromethanesulfinate Promoted by Phosphorus Reagents

Direct trifluoromethylthiolation and trifluoromethylsulfinylation reactions by using sodium trifluoromethanesulfinate were promoted by different phosphorus reagents to selectively occur under mild and transition-metal-free conditions. In the presence of phosphorus trichloride, sodium trifluoromethanesulfinate readily underwent a reaction with indole and its derivatives in N,N-dimethylformamide (DMF) at room temperature to give 3-trifluoromethylthiolated products in good yields. Trifluoromethylsulfinylation reactions, however, occurred at the C-3 position when phosphorus oxychloride was used to give the corresponding sulfoxides in high yields. This protocol was further extended to the use of other sodium perfluoroalkanesulfinates.

Method for preparing trifluoro-methylmercapto-substituted indole compound

The invention discloses a method for preparing a trifluoro-methylmercapto-substituted indole compound. The method comprises the following step: by taking trifluoro-methyl sodium sulfonate as a trifluoro-methylmercapto source and triphenylphosphine as a reducing agent, under the action of a visible light catalyst eosin Y, and enabling a substituted indole compound, the trifluoro-methyl sodium sulfonate and triphenylphosphine to react with N-chloro-o-phthalimide, thereby obtaining the trifluoro-methylmercapto-substituted indole compound. The method disclosed by the invention is simple, a trifluoro-methylmercapto reagent used in the method is low in toxicity, and no heating is needed in the preparation process, so that the energy can be saved, the environment can be protected, and direct trifluoro-methylmercapto reaction of a 3-position C (sp2)-H bond of an indole compound is achieved.