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A method for introducing isopentenyl at the C3 position of indole

A technology of isopentenyl and isoprene, which is applied in organic chemistry, bulk chemical production, etc., can solve the problems of poor atom economy and increased reaction steps, and achieve the effect of low price and high atom economy

Active Publication Date: 2022-06-07
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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Problems solved by technology

However, these methods have some disadvantages. Prenyl bromide needs to be synthesized in advance, which increases the reaction steps, and needs to remove the equivalent of HBr, and the atom economy is not good.

Method used

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  • A method for introducing isopentenyl at the C3 position of indole
  • A method for introducing isopentenyl at the C3 position of indole
  • A method for introducing isopentenyl at the C3 position of indole

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Embodiment Construction

[0027] The present invention will be described below with specific examples, but the protection scope of the present invention is not limited to these examples.

[0028] 1. Pd-catalyzed reaction of indole and isoprene

[0029] In a 2.0 mL sealed pressure-resistant reaction tube, add Pd catalyst (5 mol% of indole), phosphine ligand (5 mol% of indole), additives (30 mol% of indole), and indole 1a (0.2 mol% of indole) in turn. mmol, 23.4 mg), dissolved in 0.2 mL of solvent, then added isoprene 2a (3.0 equiv (0.6 mmol), 60 μL), reacted at 70 ° C for 24 h, and added mes-trimethoxybenzene as an internal standard after completion, GC- The yield of target product 3a was detected by FID.

[0030]

[0031] Table 1. Effects of catalysts, ligands, additives, and solvents on the reaction

[0032]

[0033]

[0034] It can be seen from the results in Table 1 that when the molar ratio of indole 1a and isoprene 2a is 1:3, the reaction is carried out at 70 °C, using THF as solvent, P...

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Abstract

The invention relates to a method for introducing isopentenyl at the C3 position of indole. Specifically, using indole and isoprene as raw materials, under the promotion of a palladium catalyst / phosphine ligand, an isopentenyl group can be introduced at the C3 position of indole with high selectivity. The present invention has the following advantages: isoprene is a green bulk chemical, simple and easy to obtain, and cheap; simple indole can participate in the reaction without the need to protect NH; no leaving group, atom High economy.

Description

technical field [0001] The present invention relates to a method for introducing isopentenyl at C3 position of indole. Specifically, using indole and isoprene as raw materials, under the promotion of palladium catalyst / phosphine ligand / additive, isopentenyl group can be introduced at C3 position of indole with high selectivity. The present invention has the following advantages: both isoprene and indole can be directly obtained commercially, the price is cheap, and the isoprenyl group can be introduced with high selectivity in one step; simple indole can participate in the reaction, and NH does not need to be protected ; No leaving group is required on the substrate, and the atom economy is high. Background technique [0002] Prenyl-substituted indoles are an important class of natural product core skeletons. For example, the alkaloid TryprostainB has an isopentenyl group at the 2-position of the indole, and (-)-Flustramine B, Mollenine A, and Nocardioazine B have an indole...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/08
CPCC07D209/08Y02P20/55
Inventor 陈庆安呼延成季定纬
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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