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Preparation method of commonly used acetamidopyridine boronic acid pinacol ester

A technology of acetylaminopyridine boric acid and halogenated acetylaminopyridine, which is applied in the field of preparation of acetamidopyridine boric acid pinacol ester, and achieves the effects of convenient industrial production, simple preparation method and convenient operation

Active Publication Date: 2014-02-26
DALIAN NETCHEM CHIRAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current synthesis method is relatively backward and cannot meet the application needs of the product.

Method used

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  • Preparation method of commonly used acetamidopyridine boronic acid pinacol ester
  • Preparation method of commonly used acetamidopyridine boronic acid pinacol ester
  • Preparation method of commonly used acetamidopyridine boronic acid pinacol ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] A general method for preparing acetylaminopyridine borate pinacol ester, taking the synthesis of 2-acetylaminopyridine-4-boronic acid pinacol ester as an example:

[0023] The preparation of the first step 2-acetylamino-4-bromopyridine:

[0024] Add 45.84g (0.265mol) of 2-amino-4-bromopyridine to a 1L four-necked flask equipped with magnetic stirring and a thermometer, add 500mL of dichloromethane and stir at room temperature to dissolve, slowly add 40.52g (0.397mol) Acetic anhydride, react for 2 to 5 hours after dropping, control in TLC until the reaction is complete, distill under reduced pressure, dissolve the residue with ethyl acetate, wash twice with 200mL saturated sodium bicarbonate, and evaporate to dryness to obtain 2-acetamido-4- Bromopyridine 55.91g, yield 98.14%.

[0025] The preparation of second step 2-acetylaminopyridine-4-boronic acid pinacol ester:

[0026] Add 2-acetamido-4-bromopyridine 55.91g (0.26mol), bis(pinacolate) diboron 66.02 to a 1L four-n...

Embodiment 2

[0028] A general method for preparing acetylaminopyridine borate pinacol ester, taking the synthesis of 2-acetylaminopyridine-5-boronic acid pinacol ester as an example:

[0029] The preparation of the first step 2-acetylamino-5-bromopyridine:

[0030] Add 46.04g (0.267mol) of 2-amino-5-bromopyridine to a 1L four-necked flask equipped with a magnetic stirrer and a thermometer, add 500mL of dichloromethane and stir at room temperature to dissolve, slowly add 53.80g (0.527mol) Acetic anhydride, reacted for 2-5 hours after dropping, controlled by TLC until the reaction was completed, distilled under reduced pressure, dissolved the residue with ethyl acetate, washed twice with 200mL saturated sodium bicarbonate, and evaporated to dryness to obtain 2-acetamido-5- Bromopyridine 56.41g, yield 99.04%.

[0031] The preparation of second step 2-acetylaminopyridine-5-boronic acid pinacol ester:

[0032] Add 2-acetamido-5-bromopyridine 56.41g (0.264mol), bis(pinacolate) diboron 66.02 to...

Embodiment 3

[0034] A general method for preparing acetylaminopyridine boric acid pinacol ester, taking the synthesis of 3-acetylaminopyridine-5-boronic acid pinacol ester as an example:

[0035] The preparation of the first step 3-acetylamino-5-bromopyridine:

[0036] Add 45.04g (0.259mol) of 3-amino-5-bromopyridine to a 1L four-necked flask equipped with magnetic stirring and a thermometer, add 500mL of dichloromethane and stir at room temperature to dissolve, slowly add 26.44g (0.259mol) Acetic anhydride, reacted for 2 to 5 hours after dropping, controlled by TLC until the reaction was completed, distilled under reduced pressure, dissolved the residue with ethyl acetate, washed twice with 200mL saturated sodium bicarbonate, and evaporated to dryness to obtain 3-acetylamino-5- Bromopyridine 49.57g, yield 89.04%.

[0037] The preparation of second step 3-acetylaminopyridine-5-boronic acid pinacol ester:

[0038] Add 49.5 g (0.23 mol) of 3-acetamido-5-bromopyridine, 58.42 bis(pinacolate)...

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Abstract

The invention belongs to the field of organic compound synthesis and provides a preparation method of commonly used acetamidopyridine boronic acid pinacol ester. The preparation method comprises the following steps: 1. with halogenated aminopyridine as a starting material, reacting with acetic anhydride in dichloromethane to obtain halogenated acetamidopyridine; and 2. with dioxane as a solvent, mixing the halogenated acetamidopyridine, potassium acetate and bis(pinacolato)diboron under the protection of nitrogen and adding a catalyst ferrocene palladium chloride to react at 60-100 DEG C for 18-24 hours, thus generating the acetamidopyridine boronic acid pinacol ester. The raw materials are convenient to directly purchase from the markets. The preparation method is simple, is convenient to operate, is high in yield and is convenient for industrial production.

Description

Technical field: [0001] The invention relates to a preparation method of general-purpose acetamidopyridine borate pinacol ester. Background technique: [0002] Acetylaminopyridine structure is an important chemical intermediate, which has important uses in many organic chemical fields including medicine, pesticide, dyestuff, etc., so acetamidopyridine borate pinacol ester has broad application prospects. However, the current synthesis method is relatively backward and cannot meet the application needs of the product. Invention content: [0003] The invention provides a general preparation method of acetylaminopyridine borate pinacol ester, the raw materials are convenient to be directly purchased from the market, the preparation method is simple, the operation is convenient, the yield is high, and the industrial production is convenient. [0004] The technical scheme that the present invention adopts for realizing the above object is: a kind of general method for pre...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02
Inventor 李欣郑鹏
Owner DALIAN NETCHEM CHIRAL TECH
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