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Biaryl pyrrole derived compound and preparation method thereof

An arylpyrrole and compound technology, which is applied in the field of biarylpyrrole derivative compounds and their preparation, can solve problems such as difficulty in synthesis of biaryl compounds, and achieve the advantages of good industrial production, short reaction route, and reduction of intermediate processes.

Inactive Publication Date: 2019-06-21
TAIZHOU VOCATIONAL & TECHN COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, how to develop some new intermediate compounds, so that more novel biaryl compounds can be provided, and the problem of difficult synthesis of biaryl compounds containing 1-H-pyrrole can be solved, by designing and synthesizing pyrrole biaryl The compound is important for the development of new biphenyl blood pressure-lowering drugs

Method used

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  • Biaryl pyrrole derived compound and preparation method thereof
  • Biaryl pyrrole derived compound and preparation method thereof
  • Biaryl pyrrole derived compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The structural formula of the biarylpyrrole derivative compound Ia of the present embodiment is as follows:

[0037]

[0038] The structural formula of the corresponding formula II compound (2-phenylpyridine) in the present embodiment is as follows:

[0039]

[0040] In this embodiment, the compound is specifically synthesized by the following method:

[0041] Formula II compound (155mg, 1mmol), pyrrole (670mg, 10mmol), tert-amyl alcohol (20mL), [RuCl 2 (p-cymene)] 2(15mg, 0.025mmol) and copper acetate monohydrate (500mg, 2.5mmol) were put into a clean reaction container, the gas in the container was replaced with oxygen three times and then sealed with a pressure-resistant tetrafluoro bottle stopper, and then the temperature was raised to 105 ° C ~ 110 ℃, in the presence of oxygen, keep warm for oxidative dehydrogenation coupling reaction for 24 hours, after the reaction, slowly cool the reaction solution to room temperature, filter the synthetic solution, rins...

Embodiment 2-8

[0047] Synthesize the corresponding product biarylpyrrole derivative compound Ia according to the operation process of the above-mentioned Example 1, by changing the raw material pyrrole, the catalyst [RuCl 2 (p-cymene)] 2 The consumption and solvent type carry out corresponding concrete implementation, and various consumption ratio situation and corresponding product yield result are as shown in table 1 below:

[0048] Table 1:

[0049]

[0050] For [RuCl in the above table 1 2 (p-cymene)] 2 The consumption is expressed as 30mg (5%mmol) in corresponding embodiment 2 [RuCl 2 (p-cymene)] 2 The dosage of the compound is 30 mg, accounting for 5% mmol of the dosage of the raw material compound of formula II.

[0051] The structural analysis of the product Ia corresponding to Examples 2-8 can be consistent with the corresponding results in Example 1.

Embodiment 9

[0053] The structural formula of the biarylpyrrole derivative compound Ib of the present embodiment is as follows:

[0054]

[0055] The structural formula of the corresponding formula II compound (2-biphenylpyridine) in the present embodiment is as follows:

[0056]

[0057] In this embodiment, the compound is specifically synthesized by the following method:

[0058] Formula II compound (231mg, 1mmol) (2-biphenylpyridine), pyrrole (429mg, 8mmol), tert-butanol (30mL), [RuCl 2 (p-cymene)] 2 (15mg, 0.025mmol) and copper acetate monohydrate (500mg, 2.5mmol) were put into a clean reaction container, the gas in the container was replaced with oxygen three times and then sealed with a pressure-resistant tetrafluoro bottle stopper, and then the temperature was raised to 105 ° C ~ 108 ℃, in the presence of oxygen, keep warm for oxidative dehydrogenation coupling reaction for 22 hours, after the reaction, slowly cool the reaction solution to room temperature, filter the synthe...

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Abstract

The invention relates to a biaryl pyrrole derived compound and a preparation method thereof, and belongs to the technical field of drug intermediate synthesis. The biaryl pyrrole derived compound solves the problem of providing a class of compounds of novel structures, and a synthesis method has the advantages of short synthesis route and easy synthesis. According to the preparation method of thederived compound, (RuCl2 (p-cymene)) 2 and bivalent copper salt are taken as a composite catalyst, and raw materials and pyrrole are subjected to oxidative dehydrogenation coupling reaction in the presence of oxygen, so as to obtain a corresponding product. The compound and the preparation method have the advantages that active 1-H-pyrrole biaryl can be effectively introduced, the compound is of significance for synthesis and development of intermediate compounds of more novel antihypertensive drugs, the reaction route is short, and the method is easy to operate.

Description

technical field [0001] The invention relates to a biarylpyrrole derivative compound and a preparation method thereof, belonging to the technical field of pharmaceutical intermediate synthesis. Background technique [0002] Biaryl compounds, especially biaryl compounds containing heteroatoms such as N and O, are the structural skeleton in the active ingredient molecule of clinical antihypertensive drugs, such as: angiotensin II (AT1) receptor antagonists sartan Blood pressure medicines Azilsartan, Valsartan, etc. [0003] [0004] In the prior art, it is generally used to synthesize biaryl compounds on an experimental scale, and palladium catalysts and nickel catalysts are used. Although existing nickel catalysts are also economically beneficial, palladium catalysts have low toxicity and resistance to functional groups. Greater tolerance over nickel catalysts. Therefore, most of the existing biaryl compounds are obtained through the Suzuki reaction of aryl halides and ar...

Claims

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Application Information

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IPC IPC(8): C07D401/10
Inventor 陈云华周丽萍叶海伟
Owner TAIZHOU VOCATIONAL & TECHN COLLEGE
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