Post-treatment purification method of pyrrole-pyridine-pyrrole compound

A purification method and compound technology, applied in the direction of organic chemistry, can solve the problems of time-consuming, consumption, multi-solvent, etc., and achieve the effect of shortening the reaction time, high product purity, and improving the purity

Inactive Publication Date: 2019-07-12
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] As can be seen from the above-mentioned prior art, compound (1) is a kind of intermediate of preparation expanded porphyrin, and it is a kind of pyrrole-pyridine-pyrrole compound, is formed by corresponding 3,4-diethyl- 5-boronate-1H-pyrrole-2-ethyl acetate and 2,6-dibromopyridine are obtained through Suzuki-Miyaura cross-coupling reaction, and the post-processing purification method involves column chromatography separation and purification, which is time-consuming and expensive Solvent, and the properties of the obtained compound are brownish yellow, indicating that there are still some residual pigments

Method used

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  • Post-treatment purification method of pyrrole-pyridine-pyrrole compound
  • Post-treatment purification method of pyrrole-pyridine-pyrrole compound
  • Post-treatment purification method of pyrrole-pyridine-pyrrole compound

Examples

Experimental program
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Effect test

Embodiment 1

[0026] This example expands the synthesis of a pyrrole-pyridine-pyrrole compound as an example of a porphyrin intermediate. The synthetic reaction equation is as follows:

[0027]

[0028] Including the following steps:

[0029] (1) Add compound B (0.3070g), palladium acetate (0.0291g), triphenylphosphine (0.0681g) and potassium carbonate (0.5916g) in a round bottom flask of appropriate size;

[0030] (2) remove the air in the bottle under reduced pressure, blow nitrogen, and repeat three times;

[0031] (3) Add N,N-dimethylformamide (20mL) and water (10mL) under nitrogen protection;

[0032] (4) The system was stirred and reacted at 85°C for about 1 hour;

[0033] (5) A solution of N,N-dimethylformamide (10 mL) dissolved in Compound A (1.0 g) was slowly added dropwise to the system;

[0034] (6) After the dropwise addition, the system was stirred and reacted at 85° C. for 24 hours under the protection of nitrogen;

[0035] (7) reaction finishes, and decompression remov...

Embodiment 2

[0041] This example expands the synthesis of a pyrrole-pyridine-pyrrole compound as an example of a porphyrin intermediate. The synthetic reaction equation is as follows:

[0042]

[0043] Including the following steps:

[0044] (1) Add compound B (0.614g), palladium acetate (0.0582g), triphenylphosphine (0.1362g) and potassium carbonate (1.1832g) in a round bottom flask of appropriate size;

[0045] (2) remove the air in the bottle under reduced pressure, blow nitrogen, and repeat three times;

[0046] (3) Add N,N-dimethylformamide (40mL) and water (20mL) under nitrogen protection;

[0047] (4) The system was stirred and reacted at 85°C for about 1 hour;

[0048] (5) A solution of N,N-dimethylformamide (20 mL) dissolved in Compound A (2.0 g) was slowly added dropwise to the system;

[0049] (6) After the dropwise addition, the system was stirred and reacted at 85° C. for 24 hours under the protection of nitrogen;

[0050] (7) reaction finishes, and decompression remove...

Embodiment 3

[0056] This example expands the synthesis of a pyrrole-pyridine-pyrrole compound as an example of a porphyrin intermediate. The synthetic reaction equation is as follows:

[0057]

[0058] Including the following steps:

[0059] (1) Add compound B (1.5350g), palladium acetate (0.1455g), triphenylphosphine (0.3405g) and potassium carbonate (2.9580g) in a round bottom flask of appropriate size;

[0060] (2) remove the air in the bottle under reduced pressure, blow nitrogen, and repeat three times;

[0061] (3) Add N,N-dimethylformamide (100mL) and water (50mL) under nitrogen protection;

[0062] (4) The system was stirred and reacted at 85°C for about 1 hour;

[0063] (5) A solution of N,N-dimethylformamide (50 mL) dissolved in compound A (5.0 g) was slowly added dropwise to the system;

[0064] (6) After the dropwise addition, the system was stirred and reacted at 85° C. for 24 hours under the protection of nitrogen;

[0065] (7) reaction finishes, and decompression remove...

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Abstract

The invention discloses a post-treatment purification method of a pyrrole-pyridine-pyrrole compound. The method comprises the following steps: removing a solvent under a reduced pressure after the organic synthesis reaction of the pyrrole-pyridine-pyrrole compound is completed in order to obtain a crude product, adding a dissolving amount of a first organic solvent to the crude product, carrying out ultrasonic treatment to dissolve the crude product, adding a second organic solvent after the crude is completely dissolved, carrying out ultrasonic treatment to achieve dissolving, precipitating the target compound from the obtained solution, performing suction filtration, and washing the obtained precipitate with a mixed solution of the first organic solvent and the second organic solvent toobtain the high-purity pyrrole-pyridine-pyrrole compound, wherein the addition amount of the second organic solvent is 1-5 times the volume of the first organic solvent. The method adopting the ultrasonic dissolving-crystallizing process has the advantages of removal of byproducts and pigments formed in the organic synthesis reaction, simplicity in post-treatment, improvement of the purity of theorganic target product, and obtaining of the high-purity target compound.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and relates to a method for purifying compounds, in particular to a post-treatment purification method for pyrrole-pyridine-pyrrole compounds in organic chemical synthesis reactions, specifically a method for purifying pyrrole-pyrrole- Pyridine-pyrrole method. Background technique [0002] Organic synthesis reactions play a pivotal role in the field of organic synthesis and even the entire chemical industry. Improving the process route of organic synthesis and optimizing reaction conditions are the needs of the industry and the driving force for industrial progress. [0003] In the process of organic synthesis, especially in some synthesis with relatively large molecular weight, complex structure and long process route, the synthesis reaction of many compounds is not a simple and complete reaction, and is generally accompanied by the formation of various by-products, even Some pigment is formed...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14
CPCC07D401/14
Inventor 王飞刘志园陈浩郝梦娣雷川虎
Owner SHANGHAI UNIV
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