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Preparation method of heterocyclic biphenyl boric acid

A technology of heterocyclic biphenylboronic acid and cyclobiphenylboronic acid, which is applied in the field of organic synthesis, can solve the problems of inability to carry out automatic control, difficulty in manual manipulation, and limitations, so as to improve operability, shorten reaction time, overcome Difficult Effects of Low Temperatures

Active Publication Date: 2018-08-17
上海泰坦科技股份有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The research on the synthesis of various substituted aromatic ring boronic acids was first started in the 1950s abroad, and their application research has been increasing since then. However, at present, the synthesis process of heterocyclic boronic acids is mainly concentrated in conventional synthesis methods, which is very limited.
[0004] CN103601748A discloses a hydroxyalkylated heterocyclic boronic acid ester and its preparation method and use. Step 1, under the conditions of an organic solvent and a catalyst, the heterocyclic compound and an alkyl epoxide react to generate compound A; Step 2 , under the conditions of an organic solvent and a catalyst, compound B reacts with compound A or a heterocyclic alcohol, and the method used is a conventional synthesis method, which cannot be automatically controlled, and is difficult to manipulate artificially, and has limitations

Method used

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  • Preparation method of heterocyclic biphenyl boric acid
  • Preparation method of heterocyclic biphenyl boric acid
  • Preparation method of heterocyclic biphenyl boric acid

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Embodiment 1

[0036] This embodiment prepares heterocyclic biphenyl boronic acid through the following steps, wherein the compound of formula I has the structure Concrete reaction formula is as follows:

[0037]

[0038] Dissolve 0.01mol of the compound shown in formula I in solvent A tetrahydrofuran, dissolve 0.012mol dimethylaminoboronic acid pinacol ester and 0.012mol n-butyllithium in solvent B tetrahydrofuran, then dissolve solvent A and solvent B in - At 10°C, the continuous flow feeding reaction was carried out for 25 minutes, the reaction was quenched by saturated sodium chloride, after washing, the hydrolysis reaction was carried out with sodium hydroxide at 30°C for 2 hours to obtain 1-(3-phenylboronic acid)-pyrrole, the yield was 90.2 %.

[0039] 1 H NMR (400MHz, DMSO-d 6 )δ7.49-7.08 (m, 4H), 6.62-6.05 (m, 2H), 4.79 (s, 2H).

Embodiment 2

[0041] This embodiment prepares heterocyclic biphenyl boronic acid through the following steps, wherein the compound of formula I has the structure Concrete reaction formula is as follows:

[0042]

[0043] The compound shown in formula I is dissolved in solvent A ether, and dimethylaminoboronic acid pinacol ester and n-butyllithium are dissolved in solvent B ether, wherein the compound shown in formula I, dimethylaminoboronic acid pinacol ester The molar ratio to n-butyllithium is 1:1.1:1.1, and then solvent A and solvent B are subjected to continuous flow feeding reaction at 10°C for 10 min, quenched by saturated sodium chloride, washed, and used potassium hydroxide in The hydrolysis reaction was carried out at 20° C. for 3 h to obtain 3-(3-benzylboronic acid)-oxazolidine with a yield of 88.3%.

[0044] 1 H NMR (400MHz, DMSO-d 6 )δ7.56-7.11 (m, 4H), 4.83 (s, 2H), 4.44 (s, 2H), 3.47 (t, 2H), 2.53 (t, 2H).

Embodiment 3

[0046] This embodiment prepares heterocyclic biphenyl boronic acid through the following steps, wherein the compound of formula I has the structure Concrete reaction formula is as follows:

[0047]

[0048]Dissolve the compound shown in formula I in solvent A tetrahydrofuran, and dissolve dimethylaminoboronic acid pinacol ester and sec-butyllithium in solvent B, wherein the compound shown in formula I, dimethylaminoboronic acid pinacol ester The molar ratio to sec-butyllithium is 1:2.5:2, and then solvent A and solvent B are subjected to continuous flow feeding reaction at -20°C for 60 minutes, and the reaction is quenched by saturated sodium chloride. After washing, use alkaline The reagent was hydrolyzed at 40° C. for 1 h to obtain 1-(3-benzylboronic acid)-1H-indazole with a yield of 87.2%.

[0049] 1 H NMR (400MHz, DMSO-d 6 )δ8.20-8.14 (m, 1H), 7.91-7.03 (m, 8H), 4.99 (s, 2H), 4.22 (s, 2H).

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Abstract

The invention provides a preparation method of heterocyclic biphenyl boric acid. The preparation method comprises the following steps: dissolving a compound shown in formula I into a solvent A, dissolving a boronizing reagent and an organolithium reagent into a solvent B, then performing continuous flowing feeding reaction on the reagent A and the reagent B, after the reaction is finished, using an alkaline reagent for performing hydrolysis reaction to obtain the heterocyclic biphenyl boric acid; according to the preparation method provided by the invention, a flowing chemical technique is used for synthesizing a heterocyclic biphenyl boric acid compound, compared with the existing conventional reaction method, the reaction yield is increased, the yield of part of the compound can reach upto 82% or above, the reaction time is shortened, the reaction can be rapidly finished within 1 hour, and the reaction temperature is raised, the reaction can be completed at around -20 DEG C to 10 DEG C, energy loss caused by reacting at the ultralow temperature environment can be avoided; the preparation method is an excellent synthetic method, and has a good application prospect.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a preparation method of heterocyclic boronic acid, in particular to a preparation method of heterocyclic biphenyl boronic acid. Background technique [0002] Continuous flow chemistry is a new technology developed in the past ten years. Continuous flow chemistry has the advantages of high safety, fast heat and mass transfer, high degree of automation, online monitoring and purification, etc., which promotes its rapid development in organic synthesis reactions. The advantages are particularly obvious in reactions with large heat release, high temperature and high pressure, and large environmental pollution. Continuous flow chemical technology is a technology that uses pumps to provide power to carry out chemical reactions in microchannels with reactants in a continuous flow manner. Continuous flow chemistry, as an emerging synthetic reaction technology, has the potential advantage...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 谢应波张庆张华徐肖冰罗桂云张维燕
Owner 上海泰坦科技股份有限公司
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