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Method for high-selectivity synthesis of 3-thio indole

A high-selectivity, indole technology, applied in organic chemistry and other directions, can solve the problems of poor selectivity, large amount of reagents, harsh reaction conditions, etc., and achieve the effects of reducing preparation cost, convenient operation and rapid reaction.

Active Publication Date: 2021-02-26
SHANGHAI INST OF TECH
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The purpose of the present invention is to provide a method for highly selective synthesis of 3-thioether indole, which is used to solve the problems of harsh reaction conditions, large reagent consumption and poor selectivity in the existing 3-thioether indole synthesis reaction

Method used

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  • Method for high-selectivity synthesis of 3-thio indole
  • Method for high-selectivity synthesis of 3-thio indole
  • Method for high-selectivity synthesis of 3-thio indole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] A preparation method of 3-(4-methylphenylthio)indole / 3-(p-tolylthio)-1H-indole, comprising the following steps:

[0028] 1) Weigh 0.5mmol of indole, 0.6mmol of p-toluenesulfonyl hydrazide, 0.25mmol of lithium bromide, 0.1,,mmol of ammonium persulfate and add them into 2mL of ethanol solution and mix well, then stir and react at 80°C for 8-10h, to obtain a reaction mixture;

[0029] 2) The reaction mixture was dried and concentrated successively, and then using ethyl acetate / petroleum ether (1:30-1:10) as a developing solvent, the concentrate was separated by column chromatography to obtain 95.7 mg of the target product (yield is 80%).

[0030] Carry out NMR characterization to above-mentioned target product, the result is as follows:

[0031] 1 H-NMR (500MHz, CDCl 3 ):δ=8.37(s,1H), 7.67(d,J=7.9Hz,1H),7.46(d,J=11.5,5.3Hz,2H),7.30(t,J=13.0,5.1Hz,1H) ,7.21(t,J=7.5Hz,1H),7.09(d,J=8.1Hz,2H),7.02(d,J=8.1Hz,2H),2.30(s,3H);

[0032] 13 C-NMR (126MHz, CDCl 3 ): δ=136.5, ...

Embodiment 2

[0034] A preparation method of 3-(p-methoxyphenylthio)-1H-indole, comprising the following steps:

[0035] 1) Weigh 0.5mmol of indole, 0.6mmol of p-methoxybenzenesulfonyl hydrazide, lithium bromide, and ammonium persulfate and add them to 2mL of ethanol solution and mix well, then stir and react at 80°C for 8-10h to obtain a reaction mixture liquid;

[0036] 2) After the reaction mixture was dried and concentrated in sequence, the concentrate was separated by column chromatography using ethyl acetate / petroleum ether (1 / 30-1 / 10, v / v) as a developing solvent to obtain 107.2 mg of the target Product (84% yield).

[0037] Carry out NMR characterization to above-mentioned target product, the result is as follows:

[0038] 1 H-NMR (500MHz, CDCl 3 ):δ=8.42(s,1H),7.73(d,J=8.0Hz,1H),7.39(dd,J=12.6,8.5Hz,2H),7.30(t,J=11.1Hz,1H),7.23 (m,3H),6.78(d,J=8.8Hz,2H),3.77(s,3H);

[0039] 13 C-NMR (126MHz, CDCl 3 ): δ=157.8, 136.5, 130.1, 129.5, 129.0, 128.6, 123.0, 120.8, 119.6, 114.5, 1...

Embodiment 3

[0041] A preparation method of 3-(4-bromophenylthio) indole, comprising the following steps:

[0042]1) Weigh 0.5mmol of indole, 0.6mmol of brosenesulfonyl hydrazide, lithium bromide, and ammonium persulfate and add them into 2mL of ethanol solution and mix evenly, then stir and react at 80°C for 8-10h to obtain a reaction mixture;

[0043] 2) After the reaction mixture was dried and concentrated in sequence, the concentrate was separated by column chromatography using ethyl acetate / petroleum ether (1 / 30-1 / 10, v / v) as a developing solvent to obtain 115.5 mg of the target Product (76% yield).

[0044] Carry out NMR characterization to above-mentioned target product, the result is as follows:

[0045] 1 H-NMR (500MHz, CDCl 3 ):δ=8.47(s,1H),7.60(d,J=7.9Hz,1H),7.49(dd,J=16.6,4.8Hz,2H),7.30(dd,J=15.2,7.6Hz,3H) ,7.21(t,J=7.5Hz,1H),6.99(d,J=8.3Hz,2H);

[0046] 13 C-NMR (126MHz, CDCl 3 ): δ=138.6, 136.5, 131.7, 130.8, 128.8, 127.5, 123.3, 121.1, 119.5, 118.4, 111.7, 102.3.

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Abstract

The invention relates to a method for high-selectivity synthesis of 3-thio indole, which comprises the following steps: using an indole compound, a sulfonyl hydrazine compound and a bromine source toprepare a mixed solution, adding an oxidant into the mixed solution, and carrying out heating reaction at 60-100 DEG C for 8-10 hours to obtain a crude product; and sequentially carrying out drying, concentration and column chromatography separation on the crude product to obtain the 3-thio indole. Compared with the prior art, the method provided by the invention has the advantages of rapid reaction, high regioselectivity, good substrate expansibility, strong adaptability, simple preparation process, convenient operation and the like, also avoids the use of an organic metal catalyst, reduces the preparation cost, conforms to the environmental protection development concept of green chemistry, and has broad industrial application prospects.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and relates to a method for synthesizing 3-sulfide indole with high selectivity. Background technique [0002] Indole compounds have significant pharmacological and biological activities, widely exist in natural products, and have a wide range of applications in the fields of medicine, food additives and dyes. Indole is an important drug-dominant skeleton, which is usually used as a drug lead for new drug design and synthesis. Many natural indole compounds can be used as drug molecules, for example, among the more than 3000 known natural indole alkaloids, more than 40 are therapeutic drugs. As an important part of indole compounds, 3-substituted indole compounds are widely used in medicine, food additives and other fields, for example, they have been used in the treatment of heart disease, photosensitivity, cancer, AIDS and so on. Compared with traditional vulcanizing reagents, sulfony...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/30
CPCC07D209/30
Inventor 王莉贤张莹张兴华陆丹娜
Owner SHANGHAI INST OF TECH
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