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Preparation method of 3-methylsulfonyl-2-substituted benzothiophene compound

A technology of benzothiophene and methylsulfonyl, which is applied in the field of preparation of 3-methylsulfonyl-2-substituted benzothiophene compounds, can solve the problems of good economy of reaction atoms, achieve good application prospects, and avoid strong acid raw materials the effect of using

Active Publication Date: 2019-02-15
JIAXING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to provide a preparation method of 3-methylsulfonyl-2-substituted benzothiophene compound, which solves the problem of using strong acid in the synthesis of existing sulfonyl compounds, and can react under mild conditions, and Reactive atom economy is good

Method used

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  • Preparation method of 3-methylsulfonyl-2-substituted benzothiophene compound
  • Preparation method of 3-methylsulfonyl-2-substituted benzothiophene compound
  • Preparation method of 3-methylsulfonyl-2-substituted benzothiophene compound

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Embodiment 1

[0031]

[0032] A preparation method of 3-methylsulfonyl-2-phenylbenzothiophene, the method is as follows:

[0033] Add 0.2mmol o-phenylynylanisole sulfide, 0.4mmol sodium metabisulfite, xmmol% sodium methylsulfinate and 2.0mmol% Ru(bpy) to the reaction tube sequentially. 3 Cl 2 , stop the reaction tube with a rubber stopper and place it in high-purity nitrogen or argon to replace the gas, so that the system is in anaerobic conditions, add 2mL of 1,2-dichloroethane, place it around a 35-watt fluorescent lamp and stir until complete reaction until. After the reaction, the reaction solution was directly concentrated under reduced pressure, and separated by column chromatography, using a mixture of petroleum ether and ethyl acetate as the mobile phase, and purified to obtain compound 1, namely 3-methylsulfonyl-2-phenylbenzo Thiophene, and by 1 H NMR, 13 C NMR and HRMS (ESI) confirmed its structure. The structure of compound 1 is characterized as: 1 H NMR (400MHz, CDCl 3...

Embodiment 2

[0036] A preparation method for 3-methylsulfonyl-2-phenylbenzothiophene, the compound prepared is the same as in Example 1, i.e. compound 1, the difference is that the photosensitizer used is different, and the photosensitizer used in the method is acid red 87, the details are as follows:

[0037]Add 0.2mmol o-phenylynylanisole sulfide, 0.4mmol sodium metabisulfite, 0.1mmol sodium methylsulfinate and 2.0mmol% acid red 87 (CAS No. 17372-87-1), stop the reaction tube with a rubber stopper and place it in high-purity nitrogen or argon to replace the gas, so that the system is in anaerobic condition, add 2mL of 1,2-dichloroethane, and place it at 35 watts Stir around fluorescent lamp until complete reaction.

[0038] After the reaction, the post-treatment process was the same as in Example 1, and the structural characterization of compound 1 was the same as in Example 1, and the yield was 86%.

Embodiment 3

[0040] A preparation method for 3-methylsulfonyl-2-phenylbenzothiophene, the compound prepared is the same as in Example 2, i.e. compound 1, the difference is that the photosensitizer used is different, and the photosensitizer used in the method is di[ 2-(2,4-Difluorophenyl)-5-trifluoromethylpyridine][2-2'-bi(4-tert-butylpyridine)]iridium di(hexafluorophosphate) salt (CAS No. 870987 -63-6), others are identical with embodiment 2, productive rate is 90%.

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Abstract

The invention discloses a preparation method of a 3-methylsulfonyl-2-substituted benzothiophene compound. The compound has a structure represented as the formula (I). The preparation method of the compound comprises following steps: sodium methanesulfonate is oxidized in an organic solvent by a photosensitizer in an excited state at the room temperature in an inert gas environment under the irradiation of a fluorescent lamp, methylsulfonyl free radicals are generated, the methylsulfonyl free radicals perform a addition ring closing reaction on o-alkynyl thioanisole, and the 3-methylsulfonyl-2-substituted benzothiophene compound with the structure represented as the formula (I) is obtained. According to the method, the conditions are mild, reaction raw materials are easily available, furthermore, reaction atom economy is good, organic raw materials in the reaction totally participate in the reaction, and high efficiency of the chemical reaction is shown.

Description

technical field [0001] The invention relates to a preparation method of benzothiophene compounds, in particular to a preparation method of 3-methylsulfonyl-2-substituted benzothiophene compounds. Background technique [0002] For a long time, sulfonyl compound fragments widely exist in natural products and marketed drug molecules, such as gliclazide, glimepiride and other very mature drugs for treating diabetes. Because many compounds containing such sulfonyl moieties have high biological activity and potential application value, these compounds have received extensive attention and in-depth research. [0003] Reports on the organic synthesis and biological testing of sulfonyl compounds are also reported year by year. In terms of functional groups, compounds containing sulfonyl moieties can be divided into sulfone, sulfonamide, sulfonyl chloride, and sulfonate ester compounds. There are usually two main routes for the synthesis of such compounds: [0004] (1) Construct the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/62
CPCC07D333/62
Inventor 邱观音生龚新星吴劼
Owner JIAXING UNIV
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