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A kind of preparation method of indole compound

A compound and indole technology, applied in the field of heterocyclic compound preparation, can solve the problems of high price and complex catalyst, and achieve the effects of short reaction period, good reactivity and mild reaction

Active Publication Date: 2020-11-27
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] This type of method has a high yield, but the catalysts used are complex, expensive, and most of them are high-temperature systems

Method used

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  • A kind of preparation method of indole compound
  • A kind of preparation method of indole compound
  • A kind of preparation method of indole compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: the impact of different catalyst additions on synthetic effect

[0036] During the preparation process, we tried a variety of catalysts, and finally determined that silver oxide had the best catalytic effect. Using this catalyst not only improved the reactivity of raw materials, but also promoted the forward progress of the reaction; then we The addition ratio of the catalyst was also tested, see Table 1 for details.

[0037] Table 1 The influence of different catalyst additions on the synthesis effect

[0038]

[0039]

[0040]The starting material is N,N'-dimethyl(2-phenylethynyl)aniline (2mmol), silver oxide is used as catalyst, solvent is 1,2-dichloromethane (10ml), p-toluenesulfonic acid monohydrate (2mmol, i.e. 1 equivalent) exists, 40 ℃ of reaction temperature, add the catalyst of different amount according to table 1, the result shows: when catalyst amount is on the low side (referring to serial number 1,2,3 in table 1), because catalyst is ...

Embodiment 2

[0041] Embodiment 2: The influence of different atmospheric reagents on synthetic effect

[0042] In our above preparation process, the atmosphere reagent is mainly to guide the forward reaction (ie 2-ethynyl aniline derivative → indole compound). In the previous research, we initially characterized the type of atmosphere reagent as an acid reagent; In further experiments, we used the same raw materials and reaction time to conduct experiments in different systems composed of different acids, and comprehensively considered the indicators such as the time of the reaction end point, the stability of the compound, and the purity of the compound in different systems. The results showed that p-toluenesulfonic acid monohydrate (p-TSA·H 2 (2) when the guiding effect to reaction is the best, at this moment, reaction remains to carry out under middle-acid condition, and silver oxide can be fully contacted with raw material.

[0043] On the basis of the above work, we also conducted ex...

Embodiment 3

[0052] Embodiment 3: Indole (A 1 ) preparation

[0053] In a 25mL round-bottomed flask, add N,N'-dimethyl(2-phenylethynyl)aniline (442.6mg, 2mmol), silver oxide (23.1mg, 0.1mmol), p-toluenesulfonic acid monohydrate (380.4 mg, 2mmol), 1,2-dichloromethane (10mL), stirred in an oil bath at 40°C for 3 hours, spin-dried, and passed through the column with petroleum ether:ethyl acetate=50:1 to obtain 393.9mg of the target compound, light yellow Solid, yield 95%.

[0054] A 1 The structure is shown in formula (1), and the product structure is detected, and the results are shown in the attached Figure 1A and Figure 1B .

[0055]

[0056] 1-methyl-2-phenyl-1H-indole

[0057] 1 H NMR (400MHz, CDCl 3 )δ7.71(dt,J=8.0,1.0Hz,1H),7.61–7.50(m,4H),7.49–7.40(m,2H),7.35–7.27(m,1H),7.49–7.40(m, 1H), 6.64(s, 1H), 3.81(s, 3H);

[0058] 13 C NMR (101MHz, CDCl 3 )δ141.60, 138.38, 132.88, 129.41, 128.52, 127.99, 127.88, 121.69, 120.51, 119.89, 109.64, 101.68, 31.20.

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Abstract

The invention provides a preparation method for an indole compound, and belongs to the technical field of preparation of heterocyclic compounds. The preparation method comprises the following steps: with 1,2-dichloromethane as a solvent, silver oxide as a catalyst and 2-ethynylaniline and derivatives thereof as raw materials, subjecting the raw materials to a complete reaction at 10 to 60 DEG C inthe presence of p-toluenesulfonic acid monohydrate, carrying out spin-drying so as to obtain a crude product, and carrying out column chromatographic separation so as to obtain a fine product namelythe indole compound. The preparation method provided by the invention has the advantages of short preparation steps, mild reaction conditions, high product yield and low cost, and provides a universalnovel method for preparation of the indole compound.

Description

technical field [0001] The application relates to a preparation method of indole compounds, belonging to the technical field of preparation of heterocyclic compounds. Background technique [0002] The basic skeleton of indole compounds is a benzopyrrole ring, and these compounds are widely found in active organisms, natural products and drug molecules. Compounds with indole as the basic core structure have various pharmacological activities such as antitumor, anti-inflammatory, and antibacterial. According to reports, diindolylmethane can not only inhibit the growth of tumor cells, induce cell apoptosis, but also inhibit angiogenesis. Vincristine, a drug with high anti-cancer effect, also has the basic skeleton of indole, which makes more and more pharmaceutical workers have a strong interest in the synthesis of indole compounds. [0003] At present, the common methods for synthesizing the basic skeleton of indole compounds are as follows: [0004] (1) In the presence of ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/08C07D209/12C07D209/10A61P35/00
CPCA61P35/00C07D209/08C07D209/10C07D209/12
Inventor 徐慧婷蔡涛沈润溥杜奎余乐茂骆翔罗蒙强丰诚杰
Owner SHAOXING UNIVERSITY
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