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Synthesis method of sulfonyl secondary amine compound

A technology of secondary sulfonyl amine and synthesis method, which is applied in the field of synthesis of secondary sulfonyl amine compounds, can solve the problems of relying on self-synthesis, limited sulfonyl chloride reagents and the like, and achieves the effect of good guiding significance and application prospect.

Active Publication Date: 2021-04-20
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, commercial sulfonyl chloride reagents are relatively limited, and sulfonyl chlorides with complex substituents and many heterocyclic sulfonyl chlorides have not been commercialized, relying on self-synthesis

Method used

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  • Synthesis method of sulfonyl secondary amine compound
  • Synthesis method of sulfonyl secondary amine compound
  • Synthesis method of sulfonyl secondary amine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] At room temperature, place the dry test tube reaction tube in high-purity nitrogen or argon to replace the gas, so that the system is in anhydrous and oxygen-free conditions, then add 1.0mL of acetonitrile and 0.5mmol of sulfuryl chloride and cool to 0°C, and then dropwise add 0.2 mmol of morpholine and 0.53 mmol of triethylamine were placed in a heating device at 50° C. and stirred for 0.5 hours.

[0035] Take another reaction tube, add 0.02mmol of bisbenzonitrile palladium dichloride, 0.04mmol of tris(2,6-dimethoxyphenyl)phosphine, 0.6mmol of disodium hydrogen phosphate and 0.4mmol of 2 -Naphthylboronic acid, place the reaction tube in high-purity nitrogen or argon to replace the gas, so that the system is in anhydrous and oxygen-free conditions, add 1.0mL tetrahydrofuran and 0.5mL acetonitrile, and then add the mixed solution obtained in the previous step with a syringe, and the obtained The mixture was stirred in a heating apparatus at 70°C for 16 hours....

Embodiment 2

[0038]

[0039] At room temperature, place the dry test tube reaction tube in high-purity nitrogen or argon to replace the gas, so that the system is in anhydrous and oxygen-free conditions, add 1.5mL of acetonitrile and 0.5mmol of sulfuryl chloride and cool to 0 ° C, and then dropwise add 0.2 mmol of morpholine and 0.5 mmol of triethylamine were placed in a heating device at 30° C. and stirred for 0.5 hours.

[0040] Another reaction tube was taken, and 0.01 mmol of bisbenzonitrile palladium dichloride, 0.02 mmol of tris(2,6-dimethoxyphenyl) phosphine, 0.6 mmol of disodium hydrogen phosphate and 0.4 mmol of 4 -Bromophenylboronic acid, place the reaction tube in high-purity nitrogen or argon to replace the gas, so that the system is in anhydrous and oxygen-free conditions, then add 1.0mL tetrahydrofuran and 0.5mL acetonitrile, then add the mixed solution obtained in the previous step with a syringe, and The resulting mixture was stirred in a 70°C heating apparatus for 16 ho...

Embodiment 3

[0043]

[0044] At room temperature, place the dry test tube reaction tube in high-purity nitrogen or argon to replace the gas, so that the system is in anhydrous and oxygen-free conditions, then add 3.0mL of acetonitrile and 0.9mmol of sulfuryl chloride and cool to 0°C, then dropwise add 0.6 mmol of morpholine and 1.6 mmol of triethylamine were placed in a heating device at 50° C. and stirred for 1 hour.

[0045] Another reaction tube was taken, and 0.009 mmol of bisbenzonitrile palladium dichloride, 0.018 mmol of tris(2,6-dimethoxyphenyl) phosphine, 1.5 mmol of disodium hydrogen phosphate and 1.0 mmol of 4 -Vinylphenylboronic acid, place the reaction tube in high-purity nitrogen or argon to replace the gas, so that the system is in anhydrous and oxygen-free conditions, add 3.0mL tetrahydrofuran and 1.5mL acetonitrile, and then add the mixed solution obtained in the previous step with a syringe, The resulting mixture was stirred in a heating apparatus at 50°C for 24 hours....

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Abstract

The invention belongs to the technical field of organic chemistry, and particularly relates to a preparation method of a sulfonyl secondary amine compound. The structure of the compound is characterized by 1H NMR, 13C NMR and HRMS and is confirmed. According to the method, acetonitrile and tetrahydrofuran are used as a mixed solvent, corresponding secondary amine, sulfonyl chloride and boric acid react under the heating condition in the presence of a palladium catalyst, a ligand and alkali, the secondary amine and the sulfonyl chloride firstly generate corresponding amino sulfonyl chloride, and then the amino sulfonyl chloride and the boric acid are subjected to a palladium-catalyzed Suzuki-Miyaura coupling reaction to obtain the target sulfonyl secondary amine compound. The preparation method of the compound has the advantages that corresponding sulfonyl chloride is prevented from being prepared in advance, meanwhile, the conditions are mild, the compatibility of functional groups is high, separation and purification are convenient, and good application value is achieved.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, in particular to a method for synthesizing secondary sulfonamide compounds Background technique [0002] Japanese scientist Akira Suzuki won the 2010 Nobel Prize in Chemistry for their research on "Palladium-catalyzed cross-coupling in organic synthesis". Palladium-catalyzed cross-coupling is the most advanced tool available to chemists today, according to the Nobel Committee of the Royal Swedish Academy of Sciences in its award certificate. This chemical tool has greatly improved the possibility for chemists to create advanced chemical substances. This achievement is widely used in the fields of pharmaceuticals, electronics, and advanced materials. It allows humans to create complex organic molecules, which are widely used in medicine, Synthesis of materials and natural products. [0003] The Suzuki-Miyaura reaction has been discovered since 1979 [(a) N.Miyaura, K.Yamada, A.Suzuki, T...

Claims

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Application Information

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IPC IPC(8): C07B45/00C07D295/26C07D401/04C07J43/00
Inventor 王雪枫张俊匡云艳
Owner FUDAN UNIV
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