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Synthetic method of benzothiophene[3,2-b]indol derivative

A technology of indole derivatives and benzothiophene is applied in the field of synthesis of benzothiophene [3,2-b]indole derivatives and achieves the effects of low cost, cheap raw materials and simple operation

Active Publication Date: 2018-11-06
BIRDO (SHANGHAI) PHARMATECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0024] However, in all these synthetic methods, no N-R 3 -2-((2-bromophenyl) ethynyl) aniline (II) compound is used as raw material, under the action of oxidant and catalyst, the stepwise serial oxidative coupling reaction of the substrate occurs with potassium ethyl xanthate, and simultaneously realizes the indium Synthesis of Indole Ring and Thiophene Ring
A similar method is to use 2-(2-iodophenyl)-1 hydrogen-indole in simple iodine, potassium sulfide and cuprous iodide (Huang, H.; Dang, P.; Wu, L.J.; Liang, Y.; Liu, J.B.TetrahedronLett.2016,57,574) to obtain this type of compound, but this method only realizes the synthesis of thiophene ring

Method used

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  • Synthetic method of benzothiophene[3,2-b]indol derivative
  • Synthetic method of benzothiophene[3,2-b]indol derivative
  • Synthetic method of benzothiophene[3,2-b]indol derivative

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Embodiment 1

[0044] Preparation of 10-p-toluenesulfonyl-10H-benzo[4,5]thiophene[3,2-b]indole (I-a)

[0045]

[0046]Dissolve N-p-toluenesulfonyl-2-((2-bromophenyl)ethynyl)aniline (II-a) (1mmol, 426mg) in 4mL dimethyl sulfoxide (DMSO), and add ethyl Potassium xanthate (2mmol, 320mg) and cuprous bromide (0.2mmol, 28.6mg), then slowly drop tert-butyl hydroperoxide (3mmol, 270mg), react at 80°C until TLC shows that the substrate is completely reacted . Stop heating, cool to room temperature, extract three times with water and ethyl acetate, combine the organic phase, wash the organic phase with brine, add anhydrous sodium sulfate to dry, add the organic phase to a column of silica gel and evaporate to dryness, column chromatography (ethyl acetate: petroleum ether=3:97) to obtain 294 mg of white solid (I-a) with a yield of 78%. The melting point is 157-159°C. 1 H NMR (600MHz, CDCl 3 )δ8.97(d, J=8.4Hz, 1H), 8.41(d, J=8.4Hz, 1H), 7.85(d, J=8.4Hz, 1H), 7.58(d, J=7.8Hz, 1H) ,7.53(t,J=7.2Hz,...

Embodiment 2

[0049] Preparation of 3-methyl-10-p-toluenesulfonyl-10H-benzo[4,5]thiophene[3,2-b]indole (I-b)

[0050]

[0051] Dissolve N-(2-(2-bromophenyl)ethynyl)-4-methylphenyl)-4-methylbenzenesulfonamide (II-b) (1mmol, 440mg) in 4mL DMSO (DMSO), potassium ethyl xanthate (2mmol, 320mg) and cuprous bromide (0.2mmol, 28.6mg) were added all at once, and then tert-butyl hydroperoxide (TBHP) (3mmol, 270mg) was slowly added dropwise , reacted at 80°C until TLC showed complete reaction of the substrate. Stop heating, cool to room temperature, extract three times with water and ethyl acetate, combine the organic phase, wash the organic phase with brine, add anhydrous sodium sulfate to dry, add the organic phase to a column of silica gel and evaporate to dryness, column chromatography (ethyl acetate: petroleum ether=2:98) to obtain 196 mg of white solid (I-b) with a yield of 50%. The melting point is 171-172°C. 1 H NMR (600MHz, CDCl 3 )δ8.96(d, J=8.4Hz, 1H), 8.27(d, J=8.4Hz, 1H), 7.85(d, J...

Embodiment 3

[0053] Preparation of 3-chloro-10-p-toluenesulfonyl-10H-benzo[4,5]thiophene[3,2-b]indole (I-c)

[0054]

[0055] Dissolve N-(2(2-bromophenyl)ethynyl)-4-chlorophenyl)-4-methylbenzenesulfonamide (II-c) (1mmol, 460mg) in 4mL dimethyl sulfoxide (DMSO ), potassium ethyl xanthate (2mmol, 320mg) and cuprous bromide (0.2mmol, 28.6mg) were added all at once, and then tert-butyl hydroperoxide (TBHP) (3mmol, 270mg) was slowly added dropwise, in React at 80°C until TLC shows that the substrate is completely reacted. Stop heating, cool to room temperature, extract three times with water and ethyl acetate, combine the organic phase, wash the organic phase with brine, add anhydrous sodium sulfate to dry, add the organic phase to a column of silica gel and evaporate to dryness, column chromatography (ethyl acetate: petroleum ether=2:98) to obtain 313mg of white solid (I-c) with a yield of 76% and a melting point of 198-199°C. 1 H NMR (600MHz, CDCl 3 )δ8.96(d, J=8.4Hz, 1H), 8.33(d, J=9.0...

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Abstract

The invention discloses a synthetic method of a benzothiophene[3,2-b]indol derivative. The method comprises the following steps: dissolving N-R3-2-((2-bromophenyl)acetenyl)phenylamine (II) in dimethylsulfoxide, reacting with KSC(S)OEt under the action of CuBr and TBHP to obtain a benzothiophene[3,2-b]indol derivative (I). The formula is shown in the description. The synthetic method has the advantages that the operation is simple, the raw materials are low in price and easy to obtain, the yield is relatively ideal, and the cost is relatively low and the like.

Description

technical field [0001] The invention relates to a synthesis method of benzothiophene [3,2-b] indole derivatives. Background technique [0002] Benzothieno[3,2-b]indole is an important class of heterocyclic compounds. This special skeleton has potential application value in polymer materials and biologically active drugs. For example, BTCN is a dicyanovinylisotetracycline compound. Computational results and experimental data indicate that DFT has the lowest unoccupied molecular orbital and thus may be a potential n-type or ambipolar organic semiconductor. [1] Benzothieno[3,2-b]benzothienoindole compound A has good binding affinity to ERα and ERβ, can mimic the effect of estrogen, and has potential in the treatment of menopausal symptoms and postmenopausal osteoporosis the value of [2] . Compound B can stimulate the synthesis of cloxazolamide hydroxylase to alleviate the paralysis of young rats induced by cloxazolamide [3] . In addition, compound C has been shown to be a...

Claims

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Application Information

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IPC IPC(8): C07D495/04
CPCC07D495/04
Inventor 杜云飞李巧赵晓园
Owner BIRDO (SHANGHAI) PHARMATECH CO LTD