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A kind of electrochemical synthesis method of 3-formyl indole derivatives

The technology of a formyl indole derivative and a synthesis method is applied in the field of electrochemical synthesis of 3-formyl indole derivatives, can solve the problems of harsh reaction conditions, large amount of three wastes and the like, and achieves easy availability of raw materials, simple operation, Great implementation value and socio-economic benefits

Active Publication Date: 2022-07-08
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above method has many shortcomings, such as the use of metal catalysts, oxidants, harsh reaction conditions, and large amounts of three wastes.

Method used

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  • A kind of electrochemical synthesis method of 3-formyl indole derivatives
  • A kind of electrochemical synthesis method of 3-formyl indole derivatives
  • A kind of electrochemical synthesis method of 3-formyl indole derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Preparation of N-methyl-1H-indole-3-carbaldehyde (Ia)

[0023] N-methyl-1H-indole (65.5mg, 0.5mmol), N,N,N',N'-tetramethylethylenediamine (116mg, 1.0mmol), ammonium iodide (73mg, 0.5mmol) , polyethylene glycol 400 (2mL) and water (2mL), and insert the mesh glassy carbon electrode and platinum electrode, switch on the current to adjust to constant current 5mA, stir at 80 °C for 18 hours and then extract with toluene (3 × 20 mL), the organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo, and the residue was separated by column chromatography to obtain 60 mg of light yellow solid N-methyl-1H-indole-3-carbaldehyde (Ia), yield: 75 %, the melting point is 69-70℃, and the structural formula of Ia is:

[0024]

Embodiment 2

[0025] Example 2: Preparation of N-methyl-1H-indole-3-carbaldehyde (Ia)

[0026] N-methyl-1H-indole (65.5mg, 0.5mmol), N,N,N',N'-tetramethylethylenediamine (116mg, 1.0mmol), ammonium iodide (73mg, 0.5mmol) and dimethyl sulfoxide (2mL) and water (2mL) were added to the reaction flask, and the mesh glassy carbon electrode and platinum electrode were inserted, the current was adjusted to a constant current of 5mA, and the reaction was stirred at 80 °C for 18 hours, and then extracted with toluene. (3×20 mL), the organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo, and the residue was separated by silica gel column chromatography to obtain 58 mg of light yellow solid N-methyl-1H-indole-3-carbaldehyde (Ia), which was collected Rate: 73%.

Embodiment 3

[0027] Example 3: Preparation of N-methyl-1H-indole-3-carbaldehyde (Ia)

[0028] N-methyl-1H-indole (65.5mg, 0.5mmol), N,N,N',N'-tetramethylethylenediamine (116mg, 1.0mmol), ammonium iodide (73mg, 0.5mmol) and N,N-dimethylformamide (2mL) and water (2mL) were added to the reaction flask, and the mesh glassy carbon electrode and platinum electrode were inserted, the current was adjusted to a constant current of 5mA, and the reaction was stirred at 80 °C for 18 hours. , extracted with toluene (3×20 mL), the organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo, and the residue was separated by silica gel column chromatography to obtain N-methyl-1H-indole-3-carbaldehyde (Ia) as a pale yellow solid ) 47 mg, yield: 60%.

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Abstract

The invention discloses an electrochemical synthesis method of 3-formyl indole derivatives. The method of the invention is as follows: using a non-separated electrolytic cell as a reaction vessel, adding N,N,N',N'-tetramethylethylenediamine, electrolyte, water and organic solvent into it, stirring uniformly to form a reaction solution, and then adding N,N,N',N'-tetramethylethylenediamine, electrolyte, water and organic solvent to it The positive electrode and the negative electrode of the electrode are respectively inserted into the reaction solution, and the constant current is switched on to stir the reaction. After the reaction is completed, the 3-formyl indole derivative is obtained by separation by column chromatography, and the drug depigmentation can be further prepared. The method of the invention does not need to use metal catalysts and oxidants, only electrocatalytic oxidation is used, and has the characteristics of easy availability of raw materials, simple operation, and applicable electrolytes and solvents, and has great practical value and social and economic benefits.

Description

technical field [0001] The invention belongs to the technical field of synthesis of pharmaceutical chemical intermediates, in particular to an electrochemical synthesis method of a 3-formyl indole derivative. Background technique [0002] The indole skeleton is widely present in natural active products and medicinally active molecules, for example, indomethacin, ramosetron, arbidol hydrochloride, tegaserod maleate, melatonin, etc.; wherein 3- Formyl indole derivatives are key intermediates in the synthesis of medicinally active molecules. The traditional synthesis method is mainly through indole derivatives, prepared by metal catalysis or Vilsmeier reaction. In 2011, Wu et al. reported an indole compound as the raw material, N-methylaniline as the methyl source, N,N-dimethylformamide as the solvent, tert-butyl hydroperoxide as the oxidant, and trichloride as the oxidant. Synthesis of 3-formyl indole derivatives under ruthenium catalysis (J.Am.Chem.Soc.2011,133,11924-11927....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C25B3/23C25B3/09C25B3/07C25B3/05
CPCY02P20/584
Inventor 凌飞程迪迪钟为慧
Owner ZHEJIANG UNIV OF TECH