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Preparation method of 3-indole thioether

A technology of indole sulfide and indole, which is applied in the direction of organic chemistry, can solve the problems of human injury, narrow application range, and strong odor, and achieve the effects of mild reaction conditions, wide application range, and simple post-treatment

Inactive Publication Date: 2016-03-23
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Many use thiophenol (alcohol) as vulcanization reagent in this kind of method, and smell is big, and toxicity is heavy, can cause greater harm to human body, also can pollute environment; Nuclear substitution to prepare 3-indole sulfide ( Tetrahedron 2008 , 64 , 11625.), this method generally requires the presence of substituents at the C2 and C3 positions of the indole ring at the same time, the nucleophile thiophenol (alcohol) used requires an excessive amount, and sometimes requires the presence of a phase transfer catalyst, and the conditions are relatively harsh. The least used; the third is synthesized by ring closure of 2-alkynyl-(substituted) aniline and disulfide or sulfur chloride under the action of metal catalyst or phase transfer catalyst ( Adv.Synth.Catal . 2009 , 351 ,2615, Adv.Synth.Catal . 2011 , 353 ,2739.), this method has strict requirements on the structure of the substrate, and its scope of application is narrow

Method used

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  • Preparation method of 3-indole thioether
  • Preparation method of 3-indole thioether
  • Preparation method of 3-indole thioether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: the preparation of 3-(3-methoxyphenylthio)indole

[0024]

[0025] To a 25 mL reaction flask was added indole (46.8 mg, 0.4 mmol), S-m-methoxybundt salt (242 mg, 1 mmol, 2.5 eq), elemental iodine (20 mg, 0.08 mmol), dimethyl sulfoxide ( 3mL). The reaction system was stirred and heated to 80 o C reacted for 12h. After the reaction, the reaction solution was diluted and washed with saturated sodium thiosulfate solution, and the resulting mixture was extracted four times with dichloromethane. The organic phases were combined, washed twice with water, and dried over anhydrous sodium sulfate. Finally, the solvent was evaporated, separated and purified by silica gel column chromatography (petroleum ether: ether / 20:1-4:1), and the final product 3-(m-methoxyphenylthio)indole was obtained as a white solid, (90mg, produced rate 88%). Melting point: 88-90 o c. 1 HNMR (CDCl 3 ,400MHz,ppm):δ8.42(brs,1H),7.63(d,J=8.0Hz,1H),7.41-7.46(m,2H),7.27-7.29(m,1H),7.16-...

Embodiment 2

[0026] Embodiment 2: the preparation of 3-phenylthioindole

[0027]

[0028] The experimental operation was similar to Example 1, except that the amount of dimethyl sulfoxide was 78 mg (2.5 eq.), and DMF (3 mL) was used as the solvent to obtain 3-phenylthio-indole with a yield of 84%. White solid, melting point: 152-153 o c. 1 HNMR (CDCl 3,400MHz,ppm):δ8.37(brs,1H),7.37(d, J= 7.6Hz , 1H),7.43-7.48(m,2H),7.27-7.31(t, J= 7.2Hz , 1H), 7.05-7.20 (m, 6H). 13 CNMR (CDCl 3 ,100MHz,ppm):δ139.3,136.6,130.8,129.8,128.8,126.0,124.7,123.2,121.0,119.8,111.7,102.9.HRMS(ESI):m / zcalcdforC 14 h 11 NS[M+H] + ,226.0690;found,226.0693.

Embodiment 3

[0029] Embodiment 3: the preparation of 3-(4-methylphenylthio)-indole

[0030]

[0031] The experimental operation is similar to Example 1, except that the amount of dimethyl sulfoxide is 78 mg (2.5 eq.), and NMP (3 mL) is used as a solvent to obtain 3-(4-methylphenylthio) indole, and the yield is 88%. White solid, melting point: 124-126 o C.1HNMR (CDCl 3 ,400MHz,ppm):δ8.35(brs1H),7.63(d,J=8.0Hz,1H),7.47(s,1H),7.42-7.44(d,J=8.4Hz,1H),7.25-7.29( m,1H),7.17(t,J=7.6Hz,1H),7.04(d,J=8.0Hz,2H),6.98(d,J=8.4Hz,2H).2.26(s,3H). 13 CNMR (CDCl 3 ,100MHz,ppm):δ136.5,135.6,134.8,130.6,129.6,129.2,126.4,123.1,120.9,119.8,111.7,21.0.HRMS(ESI):m / zcalcdforC 15 h 13 NS[M+H] + ,240.0847; found, 240.0845.

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Abstract

According to the invention, Bunte salt is employed as a sulfur source to prepare 3-indole thioether. At a certain temperature, elementary iodine or hydroiodic acid and salts thereof is employed as a catalyst, dimethyl sulfoxide is employed as an oxidant, and the Bunte salt is employed as the sulfur source to react with an indole compound without or with other solvents to prepare the 3-indole thioether. Reagents in the method are low in cost and easy to obtain. The method is mild in reaction conditions and is wide in substrate application. The reagents are slight in smell. The method is low in environment pollution.

Description

technical field [0001] The present invention relates to a method for preparing 3-indole sulfide. The method uses dimethyl sulfoxide as an oxidant, iodine element or iodide as a catalyst, and Bunte salt as a vulcanizing agent to react with indoles to prepare 3-indole sulfide. - Indole sulfide. Background technique [0002] As an important member of substituted indole, 3-indole sulfide and its derivatives have important medical value. According to reports, some drug molecules with 3-indole sulfide structure have good curative effect on HIV, obesity, allergy, cancer and heart disease (A ntiviralChem. Chemother. 2006, 17 ,59、 J. Med. Chem. 2006, 49 ,3172, J. Med. Chem. 2004, 47 ,6120, Nat. Rev. Drug Discovery 2005, 4 ,664、 J. Med. Chem. 1989, 32 ,1360). In addition, 3-indolesulfide is also a potent inhibitor of COX-2 and a potential inhibitor of tubulin polymerization ( J. Org. Chem .2004, 69, 7688, J. Med. Chem. 2006, 49 ,947). The method for synthesizing ...

Claims

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Application Information

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IPC IPC(8): C07D209/30C07D401/12C07D471/04
CPCC07D209/30C07D401/12C07D471/04
Inventor 罗美明齐鸿
Owner SICHUAN UNIV
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