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The preparation method of 3-alkenylindole compound

A technology of indole compound and alkenyl indole, applied in the direction of organic chemistry, etc., to achieve the effects of short reaction time, high reaction yield and easy operation

Active Publication Date: 2017-09-29
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The application of mechanical ball milling technology in the dehydrogenation coupling reaction is seldom, and there is no report on the oxidative Heck coupling reaction using the mechanical ball milling method.

Method used

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  • The preparation method of 3-alkenylindole compound
  • The preparation method of 3-alkenylindole compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] The preparation of embodiment 1 N-methyl-3-ethoxycarbonylvinylindole

[0039]Add N-methylindole (131mg, 1mmol), ethyl acrylate (50mg, 0.5mmol), palladium acetate (22.4mg, 0.1mmol), manganese dioxide (174mg, 2mmol), silica gel (550mg ), then add 2 stainless steel balls with a diameter of 10mm, cover the ball mill lid, put into the ball mill and run at a speed of 600r / min to make the mixture react for 60 minutes. TLC (sample is dissolved in ethyl acetate) tracking reaction progress, after the reaction finishes, whole reaction mixture is poured out from grinding tank, takes out stainless steel ball, and solid powder is directly mixed with sherwood oil and ethyl acetate (volume ratio 25:1 ) was separated by column chromatography, and the resulting eluate containing the target compound was evaporated and dried to obtain 68.7 mg of N-methyl-3-ethoxycarbonylvinylindole with a yield of 30%.

[0040] White solid, melting point 86-87℃, 1 H NMR (400MHz, CDCl 3 )δ7.86-7.79(m,2H,...

Embodiment 2

[0041] The preparation of embodiment 2 N-methyl-3-ethoxycarbonylvinylindole

[0042] Add N-methylindole (131mg, 1mmol), ethyl acrylate (100mg, 1mmol), palladium acetate (11.2mg, 0.05mmol), manganese dioxide (87mg, 1mmol), silica gel (550mg) into a 12mL ball mill jar , then add 2 stainless steel balls with a diameter of 10mm, cover the ball mill jar lid, put into the ball mill and run at a speed of 600r / min per minute to make the mixture react for 45 minutes. TLC (sample is dissolved in ethyl acetate) tracking reaction progress, after the reaction finishes, whole reaction mixture is poured out from grinding tank, takes out stainless steel ball, and solid powder is directly mixed with sherwood oil and ethyl acetate (volume ratio 20:1 ) was separated by column chromatography, and the resulting eluate containing the target compound was evaporated and dried to obtain 103.1 mg of N-methyl-3-ethoxycarbonylvinylindole with a yield of 45%. Physical property data is with embodiment 1. ...

Embodiment 3

[0043] The preparation of embodiment 3 N-methyl-3-ethoxycarbonylvinylindole

[0044] Add N-methylindole (131mg, 1mmol), ethyl acrylate (100mg, 1mmol), palladium acetate (11.2mg, 0.05mmol), manganese dioxide (130.5mg, 1.5mmol), silica gel ( 550mg), then add 2 stainless steel balls with a diameter of 10mm, cover the ball mill jar lid, put into the ball mill and make the mixture react for 45 minutes at a speed of 600r / min per minute. TLC (sample is dissolved in ethyl acetate) tracking reaction progress, after the reaction finishes, whole reaction mixture is poured out from grinding tank, takes out stainless steel ball, and solid powder is directly mixed with sherwood oil and ethyl acetate (volume ratio 20:1 ) was separated by column chromatography, and the resulting eluate containing the target compound was evaporated and dried to obtain 137.4 mg of N-methyl-3-ethoxycarbonylvinylindole with a yield of 60%. Physical property data is with embodiment 1.

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Abstract

The invention provides a preparation method of a 3-allyl indole compound as shown in the formula (III). The preparation method comprises the following steps: (1) adding an N-substituent indole compound as shown in the raw material formula (I), an olefin compound as shown in the formula (II), palladium acetate serving as a catalyst, manganese dioxide serving as an oxidizing agent, silica gel serving as a grinding agent, and stainless steel balls serving as a grinding medium into a stainless steel ball milling tank; sealing the ball milling tank; putting the ball milling tank into a ball mill at the rotational speed of 100 to 650 r / min for 20 to 75 minutes' ball milling reaction; conducting separation and purification on the mixture obtained after reaction, so as to obtain the 3-allyl indole compound as shown in the formula (III). As the mechanical grinding technology is applied to an oxidizing Hech coupling reaction to prepare the 3-allyl indole compound for the first time, the preparation method has the advantages that the application range of substrates is wide; the economic benefit is high; the environment is protected.

Description

(1) Technical field [0001] The invention relates to a preparation method of 3-alkenyl indole compounds, in particular to a method for preparing 3-alkenyl indole compounds by mechanical ball milling under solvent-free conditions. (2) Technical background [0002] Indole and its derivatives, as an important class of heterocyclic compounds, are one of the most diverse alkaloid nuclei found so far, accounting for about a quarter of the known alkaloids. Indole alkaloids are generally complex in structure, and most of them have important biological activities. In particular, 2-substituted or 3-substituted indole compounds are widely used for anti-inflammatory (indomethacin), antiemetic (ondansetron), antihypertensive (reserpine), antidepressant (5,6- Dibromo-N,N-dimethyltryptamine indole alkaloids), anti-tumor (vinblastine and vincristine) and other fields. However, the content of most indole compounds in natural resources is extremely low, which has become the biggest obstacle ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/18
CPCC07D209/18
Inventor 俞静波贾侃彦苏为科冯雯
Owner ZHEJIANG UNIV OF TECH