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Preparation method of 2-trifluoromethyl indole derivatives

A technology of trifluoromethyl indole derivatives and groups, which is applied in the field of 2-position trifluoromethyl indole derivatives and their synthesis, and can solve problems such as poor selectivity, few product types, and low atom economy. question

Inactive Publication Date: 2011-03-23
WENZHOU UNIVERSITY
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  • Abstract
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Problems solved by technology

The disadvantage is that triphenylphosphine and trifluoroacetic acid are used as raw materials to undergo Weitig reaction, the atom economy is very low, and the reaction yield is also very low
The second route is to use o-iodoaniline and malonic acid diester or trifluoropropyne derivatives through coupling reaction. The disadvantage of this method is that the selectivity is not good, and the types of products that can be expanded are too few. Trifluoropropyne derivatives are also difficult to prepare

Method used

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  • Preparation method of 2-trifluoromethyl indole derivatives
  • Preparation method of 2-trifluoromethyl indole derivatives
  • Preparation method of 2-trifluoromethyl indole derivatives

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Embodiment Construction

[0030] In order to further specify the synthesis method of the trifluoromethyl indole derivatives with two positions, the implementation methods are specifically stated here.

[0031] Preparation of two-position trifluoromethyl indole derivative B:

[0032] Compound A (0.2mmol), primary amine (0.24mmol), [Pd] (10mol%), N-P ligand (20mol%), sodium tert-butoxide (4equiv) were placed in a 25mL round tube with polyvinyl fluoride seal In the bottom flask, inject toluene (3mL) then, seal the flask, react at reflux temperature for 3-32 hours, extract with ethyl acetate after the completion of the reaction, collect the organic layer, dry, concentrate, and purify to obtain the compound with excellent yield.

[0033] In order to further elaborate the synthesis method of the trifluoromethyl sertindole derivative with the two-position, its implementation mode is specifically stated here.

[0034] Preparation of the two-position trifluoromethyl sertindole derivative C:

[0035] 2-CF 3 I...

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Abstract

The invention belongs to a preparation method of 2-trifluoromethyl indole derivatives. The method of the invention comprises the following steps: enabling F-113a serving as a fluorine raw material to react with o-chlorobenzaldehyde or o-bromobenzaldehyde to prepare alkenyl polyhalide, than reacting with any primary amine to selectively synthesize a series of 2- trifluoromethyl indole derivatives, and finally synthesizing a series of sertindole derivatives by structural modification. The reaction is characterized in that the Pd2(dba)3 is taken as a catalyst, sodium tert-butoxide is taken as alkali under participation of nitrogen and phosphorus ligands, and toluene as a solvent. The method has the advantages of short synthetic route, short reaction time, good reaction selectivity, good yield and the like, and is simple in operation.

Description

technical field [0001] The invention relates to a 2-position bearing trifluoromethyl indole derivative and a synthesis method thereof, belonging to the technical field of organic compound technology application. Background technique [0002] Indole not only occupies an important position in heterocyclic chemistry, but also has a wide range of applications in research fields such as material science, agricultural science, and pharmacy. Among the more than 3,000 known natural indole derivatives, more than 40 are Therapeutic drugs. Indole derivatives, such as tryptophan and its metabolites, indole alkaloids, etc. are widely distributed in nature. The discovery and development of indole derivatives provides a main framework for the development of new compounds with biological activity. At present, it has been found that many derivatives with the parent structure of indole have various important biological activities. For example, toad toad pigment has unique physiological pro...

Claims

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Application Information

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IPC IPC(8): C07D209/10C07D401/04C07D401/14B01J31/24B01J31/04B01J27/13
Inventor 张兴国董淑祥李金恒汤日元
Owner WENZHOU UNIVERSITY
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