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Synthetic method of 3-bromo-5-aryl-2-(trimethylsilyl)-1-(N,N-dimethylsulfonamide)pyrrole

A technology of trimethylsilyl and dimethylsulfonyl, applied in the field of regioselective synthesis of 3-bromo-5-aryl-2--1-pyrrole, which can solve the problem of inflexible substituents and the range of reaction substrates Narrow, complex catalyst preparation process and other problems, to achieve the effect of simple synthesis method and low cost

Inactive Publication Date: 2019-02-12
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, some of these methods have disadvantages such as the need for high temperature and high pressure for the reaction, complex catalyst preparation process, narrow reaction substrate range, and inflexible substituents. Synthetic routes for substituents

Method used

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  • Synthetic method of 3-bromo-5-aryl-2-(trimethylsilyl)-1-(N,N-dimethylsulfonamide)pyrrole
  • Synthetic method of 3-bromo-5-aryl-2-(trimethylsilyl)-1-(N,N-dimethylsulfonamide)pyrrole
  • Synthetic method of 3-bromo-5-aryl-2-(trimethylsilyl)-1-(N,N-dimethylsulfonamide)pyrrole

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] The first step, the synthesis of compound 1

[0044] 2,5-bis(trimethylsilyl)-1-(N,N-dimethylsulfonylamino)pyrrole (2.06 g, 6.5 mmol), chloroform (20 mL) and hydrochloric acid ( 30 μL), react at room temperature for 0.5 h. Add an appropriate amount of saturated sodium bicarbonate solution to the round bottom flask, extract with ether (10mL×3), collect the organic phase, wash with water and saturated brine successively, anhydrous Na 2 SO 4 After drying, the solvent was evaporated under reduced pressure to obtain a colorless liquid, which was separated and purified by column chromatography using n-hexane / diethyl ether (60:1, v / v) as the eluent to obtain 1.61 g of a white solid with a yield of 78%; mp:54-58℃; 1 H NMR (500MHz, CDCl 3 )δ7.19(d, J=1.5Hz, 1H, pyrrole-H), 6.50(d, J=1.5Hz, 1H, pyrrole-H), 2.79(s, 6H, Me-H), 0.32(s, 9H,TMS-H),0.21(s,9H,TMS-H); 13 C NMR (125MHz, CDCl 3 )δ137.3, 130.41, 128.15, 122.57, 38.47, 0.46, 0.4; HRMS (ESI-TOF) for C 6 h 10 N 2 o 2...

Embodiment 2

[0058] The first step, the synthesis of compound 1

[0059] With embodiment 1.

[0060] The second step, the synthesis of compound 2

[0061] Add compound 1 (574 mg, 1.8 mmol), NBS (480.6 mg, 2.7 mmol) and THF (25 mL) into a 50 mL two-neck flask under nitrogen protection, and stir for 1 h in an ice-water bath. Add an appropriate amount of saturated sodium thiosulfate solution to the mixture, extract with ether (15mL×3), combine the organic phases, wash with water and saturated brine successively, anhydrous Na 2 SO 4 After drying, the solvent was evaporated under reduced pressure to obtain a colorless liquid, which was separated and purified by column chromatography using n-hexane / diethyl ether (60:1, v / v) as the eluent to obtain 465 mg of a colorless liquid with a yield of 80%.

[0062] The third step, synthesis of compounds 3a-3d

[0063] Add compound 2 (0.60mmol), o-methoxyphenylboronic acid (1.0mmol), 2M K 2 CO 3 (2mL), Pd(PPh 3 ) 4 (10mg, 0.01mmol) and DMF (6mL) we...

Embodiment 3

[0073] The first step, the synthesis of compound 1

[0074] With embodiment 1.

[0075] The second step, the synthesis of compound 2

[0076] Add compound 1 (636.3 mg, 2.0 mmol), NBS (445.0 mg, 2.5 mmol) and THF (30 mL) into a 50 mL two-neck flask under nitrogen protection, and stir at 0° C. for 1 h. Add an appropriate amount of saturated sodium thiosulfate solution to the mixture, extract with ether (20mL×3), combine the organic phases, wash with water and saturated brine successively, anhydrous Na 2 SO 4 After drying, the solvent was evaporated under reduced pressure to obtain a colorless liquid, which was separated and purified by column chromatography using n-hexane / diethyl ether (60:1, v / v) as eluent to obtain 557 mg of a colorless liquid with a yield of 86%.

[0077] The third step, synthesis of compounds 3a-3d

[0078] Add compound 2 (0.40mmol), o-methoxyphenylboronic acid (0.48mmol), 2M K 2 CO 3 (2mL), Pd(PPh 3 ) 4 (8 mg, 0.008 mmol) and DMF (5 mL) were used as...

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Abstract

The invention belongs to the field of chemical synthesis and relates to a synthetic method of 3-bromo-5-aryl-2-(trimethylsilyl)-1-(N,N-dimethylsulfonamide)pyrrole. A product is obtained from dimethylsulfamoylpyrrole by selective bromination, coupling reaction and trimethylsilyl migration / bromination reaction. The synthetic method can be used for synthesizing 3-bromo-5-aryl-2-(trimethylsilyl)-1hydro-pyrrole-1-N,N-dimethylsulfonamide, and the reaction process is simple. The synthetic method can introduce various types of substituent groups, and has a wider application range in synthesis of drugsand natural products and development of new materials. The synthetic method has the characteristics of mild conditions, good conversion rate, high selectivity, flexible introduction of substituent groups, and the like.

Description

technical field [0001] The invention belongs to the field of chemical synthesis and relates to a method for regioselectively synthesizing 3-bromo-5-aryl-2-(trimethylsilyl)-1-(N,N-dimethylsulfonamide)pyrrole. Background technique [0002] Substituted pyrroles are important constituent units of many natural products, and are widely used in biomedical fields such as pesticides, polymer materials, enzymes, proteins, and alkaloids. Among them, the synthesis of 3-bromo-5-aryl-2-(trimethylsilyl)-1-(N,N-dimethylsulfonamide)pyrrole is an important step in the preparation of substituted pyrrole, which widely exists in antibacterial, Antiviral and other biologically active diagnostic and therapeutic drugs. Therefore, this synthetic method has received great attention. [0003] At present, there are many synthetic methods for polysubstituted pyrroles, including the classic Paal-Knorr synthesis and some new synthetic methods, such as the use of transition metal catalyzed reactions, mul...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08
CPCC07F7/0814
Inventor 刘建辉汪煜王星旸
Owner DALIAN UNIV OF TECH
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