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Synthesis method of 2, 3-diamino indole compound

A technology of a diaminoindole and a synthesis method, applied in 2 fields, can solve the problems of high reaction temperature, expensive transition metals, unfavorable for industrialized large-scale synthesis, etc., and achieves simple operation, elimination of metal residues, and high economical applicability. Effect

Pending Publication Date: 2022-06-24
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although these methods do yield some aminoindoles and are quite effective, they essentially all use expensive transition metals and require high reaction temperatures
This is not conducive to industrial large-scale synthesis

Method used

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  • Synthesis method of 2, 3-diamino indole compound
  • Synthesis method of 2, 3-diamino indole compound
  • Synthesis method of 2, 3-diamino indole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] A method for synthesizing 2,3-diaminoindole compounds comprises the following steps: putting a stirrer into a dry 10mL three-necked flask, adding N-(2-ethynylphenyl) successively under room temperature conditions -4-toluenesulfonamide (83 mg, 0.3 mmol), isopropyl 4-aminobenzoate (219.4 mg, 1.2 mmol), tetrabutylammonium iodide (23 mg, 0.06 mmol), lithium perchlorate (83 mg, 0.75 mmol), tetramethylpiperidine oxide (2.2 mg, 5 mol%), potassium carbonate (2 equiv.), water (1.0 ml) and acetonitrile (5.0 ml). At room temperature, the platinum electrode was used as the anode and the carbon electrode was used as the cathode, and the reaction was carried out under the condition of 5 mA constant current for 10 hours. After the reaction was completed, the reaction solution was extracted with ethyl acetate, and the extracted reaction solution was transferred to a 50 ml eggplant shape In the bottle, use a Heidolph rotary evaporator, the rotation speed is 80-100rpm, the temperature is...

Embodiment 2

[0044] A stirring bar was placed in a dry 10mL there-necked flask, and N-(2-ethynylphenyl)-4-toluenesulfonamide (83mg, 0.3mmol), isopropyl 4-aminobenzoate were added successively at room temperature. (219.4 mg, 1.2 mmol), tetrabutylammonium iodide (23 mg, 0.06 mmol), lithium perchlorate (83 mg, 0.75 mmol), tetramethylpiperidine oxide (2.2 mg, 5 mol%), potassium carbonate ( 2 equiv), water (1.0 ml) and acetonitrile (5.0 ml). At room temperature, the platinum electrode was used as the anode and the carbon electrode was used as the cathode, and the reaction was carried out under the condition of 5 mA constant current for 10 hours. After the reaction was completed, the reaction solution was extracted with ethyl acetate, and the extracted reaction solution was transferred to a 50 ml eggplant shape. In the bottle, use a Heidolph rotary evaporator, the rotation speed is 80-100rpm, the temperature is 38°C, the vacuum degree is 0.1Mpa, and the process is 3min. The residue is then subje...

Embodiment 3

[0052] A stirring bar was placed in a dry 10mL there-necked flask, and N-(2-ethynylphenyl)-4-toluenesulfonamide (83mg, 0.3mmol), methyl 4-aminobenzoate ( 185.3 mg, 1.2 mmol), tetrabutylammonium iodide (23 mg, 0.06 mmol), lithium perchlorate (83 mg, 0.75 mmol), tetramethylpiperidine oxide (2.2 mg, 5 mol%), potassium carbonate (2 equiv), water (1.0 ml) and acetonitrile (5.0 ml). At room temperature, the platinum electrode was used as the anode and the carbon electrode was used as the cathode, and the reaction was carried out under the condition of 5 mA constant current for 10 hours. After the reaction was completed, the reaction solution was extracted with ethyl acetate, and the extracted reaction solution was transferred to a 50 ml eggplant shape In the bottle, use a Heidolph rotary evaporator, the rotation speed is 80-100rpm, the temperature is 38°C, the vacuum degree is 0.1Mpa, and the treatment is 3min. The residue is then subjected to column chromatography using 200-mesh co...

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Abstract

The invention discloses a synthesis method of a 2, 3-diamino indole compound, which belongs to the technical field of chemical synthesis, and comprises the following operation steps: adding o-ethynylaniline, arylamine, lithium perchlorate, tetrabutylammonium iodide and tetramethylpiperidine oxide into a three-necked bottle, finally adding a solvent, under the condition of electrification, taking a platinum electrode as an anode, and reacting for 2-4 hours to obtain the 2, 3-diamino indole compound. The preparation method comprises the following steps: by taking an organic solvent as a cathode and a carbon electrode as a cathode, stirring and reacting for 8-12 hours under a constant-current condition, after the reaction is finished, extracting reaction liquid, carrying out rotary evaporation on the extracted reaction liquid, and carrying out silica gel column chromatography separation to obtain a target product, according to the method, metal catalysis is not needed, the reaction can be carried out at normal temperature, mild reaction can be carried out in a solvent system of water and acetonitrile, the method is particularly suitable for synthesis of some drugs, the problems of metal residues and the like are fundamentally solved, and high economic applicability is achieved; the problems that expensive transition metal is basically used and higher reaction temperature is needed in the existing method are solved.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing 2,3-diaminoindole compounds. Background technique [0002] Aminoindole is an important component of a variety of plants, mainly from the biosynthesis of plant itself and microorganisms such as bacteria using tryptophan as a precursor. Some natural aminoindole alkaloids are FDA-approved for use as medicines. Specific synthetic methods for organic synthesis of aminoindole compounds. At present, the main methods for synthesizing aminoindole compounds are as follows: indole hydroxylamination reaction catalyzed by copper (II) to obtain aminoindole compounds, and metal catalysts are used to construct C-N bond at C2 or C3 position of indole. , and then the subsequent transformation can obtain aminoindole compounds, use rhodium metal to catalyze the intermolecular oxyamidation reaction to obtain aminoindole compounds, and the like. Although these m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/40
CPCC07D209/40
Inventor 黄申林徐鹏程孟祥太郑煜程皓远梁超强马天庭平欣鑫
Owner NANJING FORESTRY UNIV
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