Preparation method of N-acyl indole compound

A technology of acyl indole compound and carbon monoxide, which is applied in the field of preparation of N-acyl indole compound, can solve problems such as not widely used, and achieve the effects of strong practicability, simple post-processing, and easy operation

Active Publication Date: 2021-06-04
ZHEJIANG SCI-TECH UNIV
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Problems solved by technology

However, there are few reports on the synthesis of N-acylindole compounds based on carbonylation reactions, and the current application is not widespread, but it has great application potential and needs to be further studied

Method used

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  • Preparation method of N-acyl indole compound
  • Preparation method of N-acyl indole compound
  • Preparation method of N-acyl indole compound

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Embodiment Construction

[0030] The present invention will be further described below in conjunction with specific embodiments.

[0031] Add tetrakis(triphenylphosphine)palladium, potassium carbonate, phenol 1,3,5-tricarboxylate, 2-alkynylaniline (II), and aryl iodide into a 35mL Schlenk tube according to the raw material ratio in Table 1 (III) and 2 mL of organic solvent, mixed and stirred evenly, reacted at 60° C. for 24 hours, then added silver oxide, and continued to react at 60° C. for 24 hours, as shown in Table 1. After the reaction is complete, filter, sample with silica gel, and obtain the corresponding N-acylindole compound (I) through column chromatography purification, the reaction process is shown in the following formula:

[0032]

[0033] The raw material addition of table 1 embodiment 1~15

[0034]

[0035]

[0036] Table 2

[0037]

[0038] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, Me is methyl, tBu is tert-butyl, OMe is methoxy, and ...

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Abstract

The invention discloses a preparation method of an N-acyl indole compound. The preparation method comprises the following steps: adding a palladium catalyst, potassium carbonate, a carbon monoxide substitute, 2-alkynylaniline and an aryl iodide into an organic solvent, reacting at 60 DEG C for 24 hours, then adding silver oxide, continuously reacting at 60 DEG C for 24 hours, and after the reaction is completed, carrying out post-treatment to obtain the N-acyl indole compound. The preparation method is easy to operate, the initial raw materials are cheap and easy to obtain, the reaction efficiency is high, the substrate compatibility is good, the N-acyl indole compound is efficiently and rapidly synthesized in one step, the operation is convenient, and the practicability of the method is widened.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of N-acylindole compound. Background technique [0002] Indole is an important structural skeleton widely present in natural products and drug molecules. These compounds have antitumor, anti-inflammatory, antiviral, antidiabetic, antidepressant, antihypertensive and other activities (Chem.Rev.2010,110,4489-4497; J.Heterocyclic Chem.2010,47,491-502; , 18, 6620-6662.). [0003] [0004] The carbonylation reaction provides an important method for the direct and efficient synthesis of carbonyl compounds (Chem. Rev. 2019, 119, 2090-2127). However, there are few reports on the synthesis of N-acylindole compounds based on the carbonylation reaction, and the current application is not widespread, but it has great application potential and needs to be further studied. [0005] Based on this, we developed a method for the efficient and rapid synthesis of N-acylin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/26
CPCC07D209/26Y02P20/584
Inventor 应俊吴小锋
Owner ZHEJIANG SCI-TECH UNIV
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