A method for introducing tertiary isopentenyl at C3 position of indole

A technology of tertiary isopentenyl and isoprene, applied in organic chemistry, chemical recycling, etc., can solve the problems of poor atom economy 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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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But these methods have poor atom economy and need to remove a molecule of water

Method used

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  • A method for introducing tertiary isopentenyl at C3 position of indole
  • A method for introducing tertiary isopentenyl at C3 position of indole
  • A method for introducing tertiary isopentenyl at 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.Rh-catalyzed reaction of indole and isoprene

[0029] In a 2.0 mL sealed pressure-resistant reaction tube, add Rh catalyst (5 mol% of indole), phosphine ligand (5 mol% of indole), additives (15 mol% of indole), indole 1a (0.2 mmol, 23.4 mg), dissolved in 0.2 mL of solvent, then added isoprene 2a (0.6 mmol, 60 μL), reacted at 70 °C for 24 h, and added mes-trimethoxybenzene as an internal standard after completion, and detected the target product by GC-FID 3a yield.

[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, and [Rh(cod)Cl] 2 As a catalyst, camphorsulfonic acid (CSA) is an add...

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Abstract

The invention relates to a method for introducing a tertiary isopentenyl group at the C3 position of indole. Specifically, using indole and isoprene as raw materials, under the promotion of rhodium catalyst / phosphine ligand, a tertiary 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 a tertiary isopentenyl group at the C3 position of indole. Specifically, using indole and isoprene as raw materials, under the promotion of rhodium catalyst / phosphine ligand / additive, a tertiary isopentenyl group can be introduced at the 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 tertiary isopentenyl group can be introduced with high selectivity in a single step; simple indole can participate in the reaction, and it is not necessary to carry out NH Protection; no leaving group is required on the substrate, and the atom economy is high. Background technique [0002] Tertiary isopentenyl substituted indoles are an important class of natural product core skeletons, for example, the alkaloids Echinulin and Okaramine J have tertiary isopentenyl at the 2-po...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/08
CPCC07D209/08Y02P20/584
Inventor 陈庆安呼延成季定纬
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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