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A kind of preparation method of naphthalene-1,8-diaminoarylboronamide

A technology of diaminoarylboronamide and dibenzoyl peroxide, which is applied in the field of compound preparation, can solve the problems of reduced reaction efficiency, complicated post-treatment, low yield, etc., and achieves high reaction conversion rate, low price, good tolerance effect

Active Publication Date: 2020-07-28
XIJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Obviously, this method requires two steps to complete, which undoubtedly reduces the reaction efficiency
This method also faces disadvantages such as low yield and complicated post-processing.

Method used

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  • A kind of preparation method of naphthalene-1,8-diaminoarylboronamide
  • A kind of preparation method of naphthalene-1,8-diaminoarylboronamide
  • A kind of preparation method of naphthalene-1,8-diaminoarylboronamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Add 4-methoxyaniline (24.6mg, 0.2mmol, 2.0eq.), Bpin-Bdan (29.4mg, 0.1mmol, 1.0eq.), tetrabutylammonium iodide (3.7mg , 0.01mmol, 0.1eq.), sodium acetate (12.3mg, 0.15mmol, 1.5eq.), dibenzoyl peroxide (2.4mg, 0.01mmol, 0.1eq.) and tert-butyl nitrite (20.6mg, 0.2mmol, 2.0eq.), replace the nitrogen three times, inject 0.6mL acetonitrile into the reaction tube under the nitrogen flow environment, screw the cap of the reaction tube tightly, stir vigorously at 80°C for 8 hours, stop the reaction, wait until the reaction solution drops to room temperature. The reaction solution was first filtered with diatomaceous earth to remove the reaction residue, the filter cake was washed three times with ethyl acetate, the filtrates were combined, spin-dried to obtain the target white solid 20.6 mg by column chromatography, and the yield was 75%.

[0034] The mechanism formula of the target product is:

[0035] The target product was analyzed by melting point, infrared and NMR mass...

Embodiment 2

[0043] Add 4-bromoaniline (34.2mg, 0.2mmol, 2.0eq.), Bpin-Bdan (29.4mg, 0.1mmol, 1.0eq.), tetrabutylammonium iodide (3.7mg, 0.01 mmol, 0.1eq.), sodium acetate (12.3mg, 0.15mmol, 1.5eq.), dibenzoyl peroxide (2.4mg, 0.01mmol, 0.1eq.) and tert-butyl nitrite (20.6mg, 0.2mmol , 2.0eq.), replace the nitrogen three times, inject 0.6mL acetonitrile into the reaction tube under the nitrogen flow environment, tighten the cap of the reaction tube, stir vigorously at 80°C for 8 hours, stop the reaction, and wait for the reaction solution to drop to room temperature. The reaction solution was firstly filtered with diatomaceous earth to remove the reaction residue, the filter cake was washed three times with ethyl acetate, the filtrates were combined, and the solvent was spin-dried to obtain 20.0 mg of a white solid with a yield of 62% by column chromatography.

[0044] The mechanism formula of the target product is:

[0045] The target product was analyzed by infrared and NMR mass spect...

Embodiment 3

[0051] Add 2-methylaniline (21.4mg, 0.2mmol, 2.0eq.), Bpin-Bdan (29.4mg, 0.1mmol, 1.0eq.), tetrabutylammonium iodide (3.7mg, 0.01mmol, 0.1eq.), sodium acetate (12.3mg, 0.15mmol, 1.5eq.), dibenzoyl peroxide (2.4mg, 0.01mmol, 0.1eq.) and tert-butyl nitrite (20.6mg, 0.2 mmol, 2.0eq.), replace the nitrogen three times, inject 0.6mL acetonitrile into the reaction tube under the nitrogen flow environment, tighten the cap of the reaction tube, stir vigorously at 80°C for 8 hours, stop the reaction, and wait for the reaction solution to drop to room temperature . The reaction solution was first filtered with diatomaceous earth to remove the reaction residue, the filter cake was washed three times with ethyl acetate, the filtrates were combined, and the solvent was spin-dried to obtain 11.6 mg of a white solid with a yield of 45% by column chromatography.

[0052] The mechanism formula of the target product is:

[0053] The target product was analyzed by melting point, infrared and...

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PUM

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Abstract

The invention provides a preparation method for naphthyl-1,8-diaminoarylboramide. The preparation method comprises the following steps: sequentially adding Bpin-Bdan, tetrabutylammonium iodide, sodiumacetate, dibenzoyl peroxide and tert-butyl nitrite into a reaction vessel, adding arylamine and acetonitrile in a nitrogen atmosphere, carrying out heating and vigorous stirring for a reaction, filtering an obtained reaction liquid, performing spin-drying of a solvent, and carrying out column chromatographic separation so as to obtain the target product. The method of the invention is quick and efficient in reaction, and functional groups have good tolerance and are compatible with halogen, ester groups, hydroxyl groups, cyano groups, amino groups and the like.

Description

technical field [0001] The invention belongs to the technical field of compound preparation, and in particular relates to a preparation method of naphthalene-1,8-diaminoaryl boronamide. Background technique [0002] At present, because organoboron compounds are widely used in synthetic chemistry, drug development, and chemical synthesis of materials, they have attracted more and more attention from chemists, so chemists are committed to exploring various methods for efficiently synthesizing organoboron compounds. In addition to arylboronic acid, arylboronic esters and arylboronamides with higher stability, stronger reactivity and better controllable reactivity have shown better application prospects. As very useful synthons, organoboron compounds can react with many functional groups to form new carbon-carbon or carbon-heterobonds. One of the most commonly used methods for the synthesis of aryl boronic acids is to use aryl halides as starting materials, first convert them i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02
CPCC07F5/02
Inventor 丁思懿程凯停程垚赵芃程于菲
Owner XIJING UNIV
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