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Preparation method of (3-(3-(dimethylamino) propoxy) phenyl) boronic acid

A technology of dimethylaminochloropropane and dimethylamino, which is applied in the field of preparation of propoxy)phenyl)boronic acid, can solve problems such as unsuitable for scale-up production, harsh reaction conditions, and high risk of reagents, and meets the reaction conditions and is easy Control, ease of purification, and ease of operation

Inactive Publication Date: 2017-09-22
CHEMSHUTTLE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The commonly used methods for synthesizing boronic acid compounds include methods such as Suzuki coupling and borate addition after lithium reagent dehydrogenation. scale up production

Method used

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  • Preparation method of (3-(3-(dimethylamino) propoxy) phenyl) boronic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A method for preparing (3-(3-(dimethylamino)propoxy)phenyl)boronic acid includes the following steps:

[0026] (1) Preparation of 3-hydroxyphenylboronic acid pinacol ester

[0027] Add 3-hydroxyphenylboronic acid (5g, 36.26mmol, 1.0eq) and dichloromethane (150mL) to a 500mL single-neck flask, add pinacol (5.1g, 43.51mmol, 1.2eq) under stirring, and stir at room temperature for 72h. The reaction solution was poured into water (200mL), the mixed solution was poured into a separatory funnel, the organic phase was separated, the aqueous phase was extracted twice with dichloromethane (200mL), the combined organic phases were dried with anhydrous sodium sulfate, filtered and evaporated to dryness The crude product was purified by column chromatography (200-300 mesh silica gel, dichloromethane / methanol mixed solvent with a volume ratio of 100 / 1 as the eluent) to obtain 7.0 g of white solid with a yield of 88% and a purity of 96%.

[0028] (2) Preparation of (3-(3-(dimethylamino)prop...

Embodiment 2

[0034] A method for preparing (3-(3-(dimethylamino)propoxy)phenyl)boronic acid includes the following steps:

[0035] (1) Preparation of 3-hydroxyphenylboronic acid pinacol ester

[0036] Add 3-hydroxyphenylboronic acid (10.0g, 72.46mmol, 1.0eq) and dichloromethane (300mL) to a 500mL single-neck flask, add pinacol (10.0g, 84.60mmol, 1.2eq) under stirring, and stir at room temperature for 48h The reaction solution was poured into water (400mL), the mixed solution was poured into a separatory funnel, the organic phase was separated, the aqueous phase was extracted twice with dichloromethane (400mL), the combined organic phase was dried with anhydrous sodium sulfate, filtered and evaporated Dry, the crude product was purified by column chromatography (200-300 mesh silica gel, dichloromethane / methanol mixed solvent with a volume ratio of 100 / 1 as eluent) to obtain 15.0 g of white solid with a yield of 94% and a purity of 97%.

[0037] (2) Preparation of (3-(3-(dimethylamino)propoxy)phen...

Embodiment 3

[0042] A method for preparing (3-(3-(dimethylamino)propoxy)phenyl)boronic acid includes the following steps:

[0043] (1) Preparation of 3-hydroxyphenylboronic acid pinacol ester

[0044] Add 3-hydroxyphenylboronic acid (50.0g, 362.32mmol, 1.0eq) and dichloromethane (1500mL) to a 3000mL three-necked flask, add pinacol (51.0g, 431.47mmol, 1.2eq) under stirring, and stir at room temperature for 96h The reaction solution was poured into water (2000mL), the mixed solution was poured into a separatory funnel, the organic phase was separated, the aqueous phase was extracted twice with dichloromethane (2000mL), the combined organic phase was dried with anhydrous sodium sulfate, filtered and evaporated Dry, the crude product was purified by column chromatography (200-300 mesh silica gel, dichloromethane / methanol mixed solvent with a volume ratio of 100 / 1 as eluent) to obtain 75.0 g of white solid, with a yield of 94% and a purity of 96%.

[0045] (2) Preparation of (3-(3-(dimethylamino)prop...

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Abstract

The invention discloses a preparation method of (3-(3-(dimethylamino) propoxy) phenyl) boronic acid. The preparation method comprises the following steps: (1) with 3-hydroxybenzeneboronic acid as a starting material, performing an esterification reaction to obtain 3-hydroxybenzeneboronic pinacol ester; (2) then, coupling the 3-hydroxybenzeneboronic acid pinacol ester with N, N-dimethylaminopropane hydrochloride to obtain (3-(3-(dimethylamino) propoxy) phenyl) boronic acid pinacol ester; (3) finally, hydrolyzing the (3-(3-(dimethylamino) propoxy) phenyl) boronic acid pinacol ester to obtain the (3-(3-(dimethylamino) propoxy) phenyl) boronic acid. The preparation method is short in process route, easy to operate, mild in reaction condition, easy to control and low in cost; by the preparation method, industrialization is easily realized, use of an expensive catalyst and use of metal alkali with relatively high danger are avoided, purification is easy and the yield rate is relatively high.

Description

Technical field [0001] The present invention relates to the technical field of the synthesis of pharmaceutical intermediates, in particular to a preparation of 3-(3-(dimethylamino)propoxy) using 3-hydroxyphenylboronic acid as a raw material through the process of esterification, coupling and hydrolysis. Phenyl) boric acid method. Background technique [0002] The introduction of dimethylamine into organic compounds is water-soluble, which can promote the absorption and delivery of drugs in the body. In the existing drugs, a large number of structures containing dimethylamino can be seen. [0003] Aryl boronic acid is a kind of organic synthesis, pharmaceutical and chemical intermediates that are relatively stable in the air, are not sensitive to moisture, can be stored for a long time, and have high reactivity. The Suzuki coupling reaction of aryl boronic acid and halogenated aromatic hydrocarbon has good position and stereo selectivity. Various chemical functional groups do not c...

Claims

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Application Information

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IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 孙光庆
Owner CHEMSHUTTLE
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