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A kind of synthetic method of indole derivative

A synthesis method and compound technology, applied in organic chemistry and other directions, can solve the problems of cumbersome reactions, expensive catalysts, low product yields, etc., and achieve the effects of expanding scope, good application prospects and research value.

Active Publication Date: 2018-05-11
WENZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] As mentioned above, although multiple methods for synthesizing indole derivatives have been disclosed in the prior art, there are still some defects in these methods, such as low product yield, too expensive catalyst or too large amount of catalyst, too cumbersome reaction, substrate Still need to expand etc.

Method used

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  • A kind of synthetic method of indole derivative
  • A kind of synthetic method of indole derivative
  • A kind of synthetic method of indole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043]

[0044] At room temperature, add 100 mmol of the above formula (I) compound, 150 mmol of the above formula (II) compound, 5 mmol of catalyst palladium acetate (Pd(OAc) 2 ), 15mmol nitrogen-containing ligand L1, 600mmol acid accelerator trifluoromethanesulfonic acid and 160mmol KF, then purged with nitrogen to keep the reaction atmosphere as an inert environment; stir and heat up to 70 ° C, and stir the reaction at this temperature for 30 hours ;

[0045] After the reaction was over, the mixture was poured into ethyl acetate, followed by saturated NaHCO 3 Wash with aqueous solution and brine, separate the aqueous layer, extract the aqueous layer with ethyl acetate, combine the organic layers (that is, combine the washed organic layer and the organic layer obtained by extraction), and wash with anhydrous Na 2 SO 4 After drying, the solvent was distilled off under reduced pressure, and the residue was purified by flash column chromatography (petroleum ether / ethyl ace...

Embodiment 2

[0048]

[0049] At room temperature, add 100mmol of the above formula (I) compound, 200mmol of the above formula (II) compound, 10mmol catalyst palladium acetate (Pd(OAc) 2 ), 20mmol nitrogen-containing ligand L1, 800mmol acid accelerator trifluoromethanesulfonic acid and 190mmol KF, then purged with nitrogen to keep the reaction atmosphere an inert environment; stir and heat up to 80°C, and stir and react at this temperature for 25 hours ;

[0050] After the reaction was over, the mixture was poured into ethyl acetate, followed by saturated NaHCO 3 Wash with aqueous solution and brine, separate the aqueous layer, extract the aqueous layer with ethyl acetate, combine the organic layers (that is, combine the washed organic layer and the organic layer obtained by extraction), and wash with anhydrous Na 2 SO 4 After drying, the solvent was distilled off under reduced pressure, and the residue was purified by flash column chromatography (petroleum ether / ethyl acetate, the vol...

Embodiment 3

[0053]

[0054] At room temperature, add 100 mmol of the above formula (I) compound, 250 mmol of the above formula (II) compound, 15 mmol of catalyst palladium acetate (Pd(OAc) 2 ), 25mmol nitrogen-containing ligand L1, 1000mmol acid accelerator trifluoromethanesulfonic acid and 220mmol KF, then purged with nitrogen to keep the reaction atmosphere an inert environment; stir and heat up to 90°C, and stir the reaction at this temperature for 20 hours ;

[0055] After the reaction was over, the mixture was poured into ethyl acetate, followed by saturated NaHCO 3 Wash with aqueous solution and brine, separate the aqueous layer, extract the aqueous layer with ethyl acetate, combine the organic layers (that is, combine the washed organic layer and the organic layer obtained by extraction), and wash with anhydrous Na 2 SO 4 After drying, the solvent was distilled off under reduced pressure, and the residue was purified by flash column chromatography (petroleum ether / ethyl acetat...

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Abstract

The invention relates to a method for synthesizing an indole derivative shown in the formula (III) (please see the specification). The method includes the steps that in a solvent and inertia gas atmosphere, when a catalyst, a nitrogen-containing ligand, an acid accelerator and KF exist, a compound in the formula (I) (please see the specification) and a compound in the formula (II) (please see the specification) are reacted, aftertreatment is carried out after the reaction is completed, and therefore the compound in the formula (III) is obtained, wherein R1 is selected from H or halogen, and R2 is selected from H, C1-C6 alkyl, C1-C6 alkoxy or halogen. According to the method, as a proper substrate, the proper catalyst, the proper nitrogen-containing ligand, the proper acid accelerator, the proper KF, the proper solvent and the like are comprehensively selected and cooperated, the range of the substrate is expanded accordingly, the indole derivative can be obtained with the good yield, the method has good application prospects and research value in the field of organic chemistry synthesis, and a brand new method is provided for synthesis of the compound.

Description

technical field [0001] The invention relates to a synthesis method of a condensed compound containing a heterocyclic ring, in particular to a synthesis method of an indole derivative, and belongs to the technical field of organic chemical synthesis. Background technique [0002] In the field of organic chemical synthesis technology, the synthesis of nitrogen-containing heterocyclic compounds has always been a research focus and focus. Indole compounds, as nitrogen-containing fused ring compounds, play an important role in many specific fields. For example, in the technical field of medicinal chemical intermediate synthesis, indole compounds often exist as important parent building blocks and active units. It also plays an important role and position in functional materials. [0003] It is precisely because of such an important role of indole compounds that people have conducted a lot of in-depth research on the synthesis of these compounds and achieved many beneficial resul...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/08C07D209/10C07D209/12
CPCC07D209/08C07D209/10C07D209/12
Inventor 陈久喜于书玲程天行胡堃戚林军刘妙昌吴华悦
Owner WENZHOU UNIV