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Method for primary amine-directed construction of 6-(4-bromo-2-fluorophenyl)indolo[1,2-a]quinoxaline

A technology of fluorophenyl and quinoxaline, applied in the field of primary amine-directed construction of 6-indolo[1,2-a]quinoxaline, which can solve the problems of difficult substrate preparation and high reaction temperature, and achieve operational Convenience, simple operation, and mild reaction conditions

Inactive Publication Date: 2019-04-16
GUILIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And in these known reactions, there are deficiencies such as reaction temperature is high, substrate is difficult to prepare, etc.

Method used

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  • Method for primary amine-directed construction of 6-(4-bromo-2-fluorophenyl)indolo[1,2-a]quinoxaline
  • Method for primary amine-directed construction of 6-(4-bromo-2-fluorophenyl)indolo[1,2-a]quinoxaline
  • Method for primary amine-directed construction of 6-(4-bromo-2-fluorophenyl)indolo[1,2-a]quinoxaline

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add 0.2 mmol of 2-(1H-indol-1-yl)aniline, 0.01 mmol of palladium chloride, 0.4 mmol of potassium persulfate and 0.4 mmol of 4-bromo-2-fluorobenzoyl to the reaction tube formic acid. Then add 2 ml of 1,4-dioxane as a solvent, stir the reaction at 78°C for 12 hours, then stop the reaction, cool to room temperature and filter, and extract the filtrate three times with ethyl acetate, combine the organic phases and use 0.5 g Dry over anhydrous magnesium sulfate, filter, and rotary evaporate under reduced pressure to obtain a crude product, which is finally separated and purified by column chromatography, and the eluent used in column chromatography is a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 35:1. Pure 6-(4-bromo-2-fluorophenyl)indolo[1,2-a]quinoxaline was obtained with a yield of 39%.

Embodiment 2

[0022] Add 0.2 mmol of 2-(1H-indol-1-yl)aniline, 0.01 mmol of palladium acetate, 0.4 mmol of potassium persulfate and 0.4 mmol of 4-bromo-2-fluorobenzoylformic acid in the reaction tube . Then add 2 ml of 1,4-dioxane as a solvent, stir the reaction at 78°C for 12 hours, then stop the reaction, cool to room temperature and filter, and extract the filtrate three times with ethyl acetate, combine the organic phases and use 0.5 g Dry over anhydrous magnesium sulfate, filter, and rotary evaporate under reduced pressure to obtain a crude product, which is finally separated and purified by column chromatography, and the eluent used in column chromatography is a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 35:1. Pure 6-(4-bromo-2-fluorophenyl)indolo[1,2-a]quinoxaline was obtained with a yield of 43%.

Embodiment 3

[0024] Add 0.2 mmol of 2-(1H-indol-1-yl)aniline, 0.01 mmol of palladium trifluoroacetate, 0.4 mmol of potassium persulfate and 0.4 mmol of 4-bromo-2-fluorobenzyl to the reaction tube Acylformic acid. Then add 2 ml of 1,4-dioxane as a solvent, stir the reaction at 78°C for 12 hours, then stop the reaction, cool to room temperature and filter, and extract the filtrate three times with ethyl acetate, combine the organic phases and use 0.5 g Dry over anhydrous magnesium sulfate, filter, and rotary evaporate under reduced pressure to obtain a crude product, which is finally separated and purified by column chromatography, and the eluent used in column chromatography is a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 35:1. Pure 6-(4-bromo-2-fluorophenyl)indolo[1,2-a]quinoxaline was obtained with a yield of 20%.

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Abstract

The invention relates to a method for primary amine-directed construction of 6-(4-bromo-2-fluorophenyl)indolo[1,2-a]quinoxaline. In a reaction test tube, 2-(1H-indol-1-yl)benzenamine and 4-bromo-2-fluorobenzoyl formic acid are added and taken as raw materials, and an acylation / cyclization reaction is carried out to prepare the 6-(4-bromo-2-fluorophenyl)indolo[1,2-a]quinoxaline in a high yield mode. The method for the primary amine-directed construction of the 6-(4-bromo-2-fluorophenyl)indolo[1,2-a]quinoxaline has the advantages that primary amine is taken as a traceless directional base to increase the step economy of the reaction; the raw materials required for the reaction are cheap and easy to obtain, the conditions are mild, the operation is simple, the selectivity is single, the separation yield is high, the industrial production is facilitated, and the method meets the development needs of green organic chemistry.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical chemical synthesis, in particular to a method for constructing 6-(4-bromo-2-fluorophenyl)indolo[1,2-a]quinoxaline guided by a primary amine. Background technique [0002] In recent years, organometallic chemistry has achieved unprecedented development and has become an important means of constructing carbon-carbon bonds and carbon-heterobonds. Directing group-assisted C–H functionalization reactions have attracted extensive attention from scientists due to their good selectivity and reactivity. After decades of development, a series of nitrogen-containing directing groups have been successfully used in C-H functionalization reactions, including primary amines, pyridines, amides, imines, oximes, enamines and various nitrogen-containing heterocycles. It is worth noting that there are very few reports on the C-H functionalization reaction of primary amines as directing groups, because primary...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 蒋光彬王守才及方华
Owner GUILIN UNIVERSITY OF TECHNOLOGY
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