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Method for preparing trifluoro-methylmercapto-substituted indole compound

A technology of trifluoromethylthio and trifluoromethyl, which is applied in the field of preparation of trifluoromethylthio substituted indole compounds, can solve problems such as complex preparation process, and achieve stable chemical properties, low toxicity and mild reaction conditions. Effect

Inactive Publication Date: 2017-05-31
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These reagents are relatively stable and easy to store, but they need to be prepared in advance, and the preparation process is relatively complicated, requiring the use of toxic or expensive fluorine reagents

Method used

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  • Method for preparing trifluoro-methylmercapto-substituted indole compound
  • Method for preparing trifluoro-methylmercapto-substituted indole compound
  • Method for preparing trifluoro-methylmercapto-substituted indole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Embodiment 1: Preparation of 3-trifluoromethylthioindole

[0014]

[0015] Eosin Y (0.01 mmol), sodium trifluoromethanesulfinate (0.3 mmol), triphenylphosphine (0.6 mmol), N-chlorophthalimide (0.3 mmol) were added to a 10 mL Schlenk tube , flushed into dry nitrogen after vacuuming (this process was repeated three times), indole (0.2 mmol) was dissolved in the ultra-dry solvent acetonitrile and the resulting solution was injected into the Schlenk tube through a syringe. The reaction was illuminated and stirred under a white LED light for 6 hours at room temperature. After the reaction was completed, the solvent was removed by rotary evaporation, and the residue was purified by silica gel column chromatography to obtain 37 mg of the product with a yield of 85%.

[0016] 1 H NMR (500MHz, CDCl 3 )δ8.45(br,1H),7.92–7.79(m,1H),7.51(d,J=2.8Hz,1H),7.45–7.39(m,1H),7.37–7.28(m,2H). 13 C NMR (125MHz, CDCl 3 )δ136.2, 133.0, 129.6 (q, J=309.7Hz), 129.6, 123.6, 121.8, 119.5, ...

Embodiment 2

[0017] Embodiment 2: Preparation of 1-methyl-3-trifluoromethylthioindole

[0018]

[0019] Eosin Y (0.01 mmol), sodium trifluoromethanesulfinate (0.3 mmol), triphenylphosphine (0.6 mmol), N-chlorophthalimide (0.3 mmol) were added to a 10 mL Schlenk tube , flushed into dry nitrogen after vacuuming (this process was repeated three times), 1-methylindole (0.2 mmol) was dissolved in the ultra-dry solvent acetonitrile and the resulting solution was injected into the Schlenk tube through a syringe. The reaction was illuminated and stirred under a white LED light for 6 hours at room temperature. After the reaction, the solvent was removed by rotary evaporation, and the residue was purified by silica gel column chromatography to obtain 43 mg of the product with a yield of 93%.

[0020] 1 H NMR (500MHz, CDCl 3 )δ7.85(d,J=7.6Hz,1H),7.40–7.31(m,4H),3.80(s,3H). 13 C NMR (125MHz, CDCl 3 )δ137.4, 137.1, 129.6 (q, J=310.4Hz), 130.4, 123.1, 121.4, 119.5, 110.0, 93.2, 33.3. 19 F NMR (...

Embodiment 3

[0021] Embodiment 3: Preparation of 1-benzyl-3-trifluoromethylthioindole

[0022]

[0023] Eosin Y (0.01 mmol), sodium trifluoromethanesulfinate (0.3 mmol), triphenylphosphine (0.6 mmol), N-chlorophthalimide (0.3 mmol) were added to a 10 mL Schlenk tube , flushed into dry nitrogen after vacuuming (this process was repeated three times), 1-benzyl indole (0.2 mmol) was dissolved in the ultra-dry solvent acetonitrile and the resulting solution was injected into the Schlenk tube through a syringe. The reaction was illuminated and stirred under a white LED light for 6 hours at room temperature. After the reaction was completed, the solvent was removed by rotary evaporation, and the residue was purified by silica gel column chromatography to obtain 57 mg of the product with a yield of 93%.

[0024] 1 H NMR (500MHz, CDCl 3 )δ7.85(d, J=7.0Hz, 1H), 7.47(s, 1H), 7.36–7.28(m, 6H), 7.16(d, J=6.5Hz, 2H), 5.34(s, 2H). 13 C NMR (125MHz, CDCl 3 )δ137.0, 136.5, 136.2, 130.6, 129.4 (q, ...

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Abstract

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.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a preparation method of trifluoromethylthio-substituted indole compounds. Background technique [0002] The improvement of lipophilicity is beneficial to improve the penetration and absorption of organic molecules, trifluoromethylthio (–SCF 3 ) has strong electric absorption and high lipophilicity, so trifluoromethyl sulfide compounds have broad application prospects in the fields of medicine, pesticides and materials. The methods for introducing trifluoromethylthio include fluorine-halogen exchange fluorination, trifluoromethylation of sulfur-containing compounds and direct trifluoromethylthiolation. Direct trifluoromethylthioation is obviously the most direct and concise method, including free radical trifluoromethylthioation, electrophilic trifluoromethylthioation, and nucleophilic trifluoromethylthioation. [0003] In the past ten years, the trifluoromethylthiolation reaction...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B45/06C07D209/30C07D209/32C07D209/42
CPCC07B45/06C07D209/30C07D209/32C07D209/42
Inventor 蔡春卜梅杰
Owner NANJING UNIV OF SCI & TECH
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