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A kind of preparation method of 3-indole sulfide

A technology of indole sulfide and indole, which is applied in the direction of organic chemistry and can solve problems such as human injury, strong odor, and harsh conditions

Inactive Publication Date: 2018-02-06
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, smell is big, 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 substrate structure and narrow application range

Method used

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  • A kind of preparation method of 3-indole sulfide
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  • A kind of preparation method of 3-indole sulfide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Preparation of 3-(3-methoxyphenylthio)indole

[0023]

[0024] Add indole (46.8 mg, 0.4 mmol), S-m-methoxybond salt (242 mg, 1 mmol, 2.5 eq), elemental iodine (20 mg, 0.08 mmol), dimethyl group to a 25 mL reaction flask Sulfoxide (3 mL). Stir the reaction system and heat to 80 o C reaction for 12 h. After the reaction, the reaction solution was diluted with saturated sodium thiosulfate solution and washed, and the resulting mixed solution was extracted four times with dichloromethane, the organic phases were combined, washed twice with water, and dried with anhydrous sodium sulfate. Finally, the solvent was evaporated, and silica gel column chromatography was separated and purified (petroleum ether: diethyl ether / 20:1-4:1) to obtain the final product 3-(m-methoxyphenylthio)indole as a white solid, (90 mg, The yield is 88%). Melting point: 88-90 o C. 1 H NMR (CDCl 3 , 400 MHz, ppm): δ 8.42(br s,1H), 7.63 (d, J = 8.0 Hz, 1H), 7.41-7.46 (m, 2H), 7.27-7.29 (m, 1H...

Embodiment 2

[0025] Example 2: Preparation of 3-phenylthioindole

[0026]

[0027] The experimental operation is similar to that of Example 1, except that the dosage of dimethyl sulfoxide is 78 mg (2.5 eq.), and DMF (3 mL) is used as the solvent to obtain 3-phenylthio-indole with a yield of 84%. White solid, melting point: 152-153 o C. 1 H NMR(CDCl 3 , 400 MHz, ppm): δ 8.37 (br s, 1H), 7.37 (d, J = 7.6 Hz , 1H), 7.43-7.48(m,2H), 7.27-7.31 (t, J = 7.2 Hz , 1H), 7.05-7.20 (m, 6H). 13 C NMR(CDCl 3 , 100MHz, ppm): δ 139.3, 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 / z calcd for C 14 H 11 NS [M + H] + , 226.0690;found, 226.0693.

Embodiment 3

[0028] Example 3: Preparation of 3-(4-methylphenylthio)-indole

[0029]

[0030] 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 the solvent to obtain 3-(4-methylphenylthio)indole. The yield was 88%. White solid, melting point: 124-126 o C .1H NMR (CDCl 3 , 400 MHz, ppm): δ 8.35 (br s 1H), 7.63 (d, J = 8.0 Hz, 1H), 7.47 (s, 1H), 7.42-7.44 (d, J = 8.4 Hz, 1H), 7.25- 7.29 (m, 1H), 7.17 (t, J =7.6 Hz,1H), 7.04(d, J = 8.0 Hz, 2H), 6.98 (d, J = 8.4 Hz, 2H). 2.26 (s, 3H). 13 C NMR (CDCl 3 , 100 MHz, ppm): δ 136.5, 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 / z calcd for C 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 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 reagent to react with indole substances to prepare 3 -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 effects on HIV, obesity, allergies, cancer and heart disease (A ntiviral Chem. 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-indole sulfide is also an effective inhibitor of COX-2 and a potential inhibitor of tubulin polymerization ( J. Org. Chem . 2004, 69, 7688, J. Med. Chem. 2006, 49 , 947). There are three main methods for synthesizing 3...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/30C07D401/12C07D471/04
CPCC07D209/30C07D401/12C07D471/04
Inventor 罗美明齐鸿
Owner SICHUAN UNIV
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