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Method for synthesizing 1H-pyrrolo[1,2-a]indol-2(3-H)-one

A synthetic method, 2-a technology, applied in the direction of organic chemistry, can solve the problems of difficult separation of mixtures, poor universality of substrates, difficult synthesis of substrates, etc., and achieve the effect of narrow melting point range, easy separation and high purity

Inactive Publication Date: 2019-01-18
NANYANG NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The above-mentioned synthetic method mainly has the following defects: 1. the substrate is difficult to synthesize, such as (1) and (2), and the operation is complicated; 2. the selectivity is poor, and the above-mentioned synthetic method obtains a mixture of two compounds, and the mixture is difficult to separate, such as (3 ); 3. The above synthetic methods have poor substrate universality and generally low yields, such as (1), (2) and (3)

Method used

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  • Method for synthesizing 1H-pyrrolo[1,2-a]indol-2(3-H)-one
  • Method for synthesizing 1H-pyrrolo[1,2-a]indol-2(3-H)-one
  • Method for synthesizing 1H-pyrrolo[1,2-a]indol-2(3-H)-one

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] A 1H-pyrrolo[1,2-a]indol-2(3-H)-one, whose general chemical structure is:

[0032]

[0033] The synthetic method of above-mentioned 1H-pyrrolo[1,2-a]indol-2(3-H)-one comprises the following steps:

[0034] (1) Under air atmosphere, N-propargyl indole, gold catalyst Me 4 t BuXPhosAuCl, NaBArF 4 Mix with 2,6-dibromopyridine in a molar ratio of 1mmol: 0.05mmol: 0.1mmol: 1.5mmol in 0.5mL 1,2-dichloroethane, heat in an oil bath at 60°C for 2h;

[0035] The gold catalyst Me 4 t BuXPhosAuCl synthesis method is: the Me 4 t BuXPhos phosphine ligand and dimethyl sulfide gold chloride were mixed in dichloromethane at a molar ratio of 1:1 in the dark, stirred at room temperature for 10 minutes, and spin-dried to obtain the product;

[0036] (2) After the reaction is completed, the reaction mixture is cooled to room temperature, and the reaction mixture is desalted, washed, concentrated, and purified to obtain that, with a yield of 86%, mp 190-192°C, 1 H NMR (400MHz, CDCl...

Embodiment 2

[0038] A 7-methyl-1H-pyrrolo[1,2-a]indol-2(3-H)-one, whose general chemical structure is:

[0039]

[0040] The synthetic method of above-mentioned 7-methyl-1H-pyrrolo[1,2-a]indol-2(3-H)-one comprises the following steps:

[0041] (1) Under air atmosphere, N-propargyl-5-methylindole, gold catalyst Me 4 t BuXPhosAuCl, NaBArF 4 Mix with 2,6-dibromopyridine in a molar ratio of 1mmol: 0.06mmol: 0.11mmol: 1.6mmol in 1mL of dichloromethane, and heat in an oil bath at 50°C for 4h;

[0042] The gold catalyst Me 4t BuXPhosAuCl synthesis method is: the Me 4 t BuXPhos phosphine ligand and dimethyl sulfide gold chloride are mixed in dichloromethane in a molar ratio of 1:1.1 in the dark, stirred at room temperature for 12 minutes, and spin-dried to obtain the product;

[0043] (2) After the reaction is completed, the reaction mixture is cooled to room temperature, the reaction mixture is desalted, washed, concentrated, and purified to obtain that, the yield is 82%, mp 212-214 ° C,...

Embodiment 3

[0045] A 7-fluoro-1H-pyrrolo[1,2-a]indol-2(3-H)-one, whose general chemical structure is:

[0046]

[0047] The synthetic method of above-mentioned 7-fluoro-1H-pyrrolo[1,2-a]indol-2(3-H)-one comprises the following steps:

[0048] (1) Under air atmosphere, N-propargyl-5-fluoroindole, gold catalyst Me 4 t BuXPhosAuCl, NaBArF 4 Mix with 2,6-dibromopyridine in a molar ratio of 1mmol: 0.055mmol: 0.11mmol: 1.8mmol in 1.5mL toluene, and heat in an oil bath at 70°C for 2h;

[0049] The gold catalyst Me 4t BuXPhosAuCl synthesis method is: the Me 4 tBuXPhos phosphine ligand and dimethyl sulfide gold chloride are mixed in dichloromethane in a molar ratio of 1:1.2 in the dark, stirred at room temperature for 15 minutes, and spin-dried to obtain the product;

[0050] (2) After the reaction is completed, the reaction mixture is cooled to room temperature, and the reaction mixture is desalted, washed, concentrated, and purified to obtain that, with a yield of 81%, mp 197-199°C, 1 ...

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Abstract

The invention discloses a method for synthesizing 1H-pyrrolo[1,2-a]indol-2(3-H)-one. The method comprises the following steps: (1) mixing a N-propargyl indole compound, a gold catalyst, i.e., Me4tBuXPhosAuCl, NaBArF4 and 2,6-dibromo-N-oxypyridine in a solvent in an air atmosphere, and carrying out a reaction in oil bath; (2) cooling the temperature of a reaction mixture to room temperature after the oil-bath reaction in the step (1) is completed, and subjecting the reaction mixture to demineralization, washing, concentrating and purifying, thereby obtaining 1H-pyrrolo[1,2-a]indol-2(3-H)-one. The method disclosed by the invention is simple, and the obtained target compound is high in yield, narrow in melting point range and high in purity.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 1H-pyrrolo[1,2-a]indol-2(3-H)-one. Background technique [0002] 1H-Pyrrolo[1,2-a]indol-2(3-H)-one and its derivatives are an important class of organic heterocycles, which have important biological activity and certain medicinal value. [0003] Luly, J.R. et al disclosed in Am.Chem.Soc.1983,105,2859 the intramolecular free radical reaction between bromobenzene and alkene under the action of light, and the reaction equation is: [0004] [0005] Li, G.; Huang et al. disclosed in Angew.Chem.Int.Ed.2008,47,346 a platinum-catalyzed intramolecular cycloisomerization reaction under an oxygen atmosphere, and the reaction equation is: [0006] [0007] Salim, M. etc. disclose the rhodium-catalyzed rhodium carbene reaction via the diazo precursor in Tetrahedron, 2000,56,8063, and the reaction equation is: [0008] [0009] The above-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 李亭李波柳文敏马勤阁
Owner NANYANG NORMAL UNIV
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