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Preparation method for hetero-spiro-ketone indole derivative

A technology for spiroketone indoles and derivatives, which is applied in the field of organic chemical synthesis, can solve the problems of low total yield, long reaction route, low yield and the like, and achieves high product yield and purity, simple operation and huge The effect of the application foreground

Inactive Publication Date: 2017-02-15
陈志龙
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Problems solved by technology

[0011] In view of this, in order to solve the defects such as long reaction route, low yield and low total yield when methyl bromination exists in the above-mentioned prior art, the present inventors have studied the heterospirone indole derivatives. The preparation method has been thoroughly studied, and after paying a lot of creative work, the present invention has been completed

Method used

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  • Preparation method for hetero-spiro-ketone indole derivative
  • Preparation method for hetero-spiro-ketone indole derivative
  • Preparation method for hetero-spiro-ketone indole derivative

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Embodiment 1

[0039] Compound 3-((1-(2-(1H-tetrazol-5-yl)phenyl)-1H-indol-5-yl)methyl-2-butyl-1,3 in formula (I) -The preparation method of diazaspiro[4,4]non-1-en-4-one specifically comprises the following steps:

[0040] Step 1: Synthesis of N-o-cyanophenyl-1H-indole-4-carbaldehyde:

[0041]

[0042] Indole-4-carbaldehyde (10.00g, 68.97mmol) was dissolved in N,N-dimethylformamide (150mL), o-fluorobenzonitrile (8.40mL, 75.86mmol) and potassium carbonate (19.03g, 137.94 mmol), stirred and refluxed for about 2h, monitored by TLC until the reaction was complete. After the temperature of the reaction solution was lowered to room temperature, it was filtered, and the filter cake was washed three times with dichloromethane (20 mL×3). The filtrates were combined, 200 mL of dichloromethane and 200 mL of water were added to the filtrate, the organic phase was separated, the aqueous phase was extracted with dichloromethane (150 mL×3), and the organic phases were combined. The organic phase was...

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Abstract

The invention relates to a novel preparation method for a hetero-spiro-ketone indole derivative. According to the method, the disadvantages in the prior art that the reaction route is long, the yield is relatively low during the bromination of methyl, the overall yield is low, and the like are overcome, and the overall yield is increased to about 43% from about 28%, so that the method has important practical significance and scientific research value and has a great application prospect in the field of pharmacy and the fields of chemistry and chemical industry.

Description

technical field [0001] The invention relates to a new preparation method of a class of heterospirone indole derivatives, which can effectively prevent and treat hypertension, coronary heart disease, migraine, pulmonary hypertension and other cardiovascular and cerebrovascular diseases, belonging to organic chemistry synthetic field. Background technique [0002] Heterospirone indole derivatives are a new type of compound with high medicinal value, which can prevent or treat hypertension, coronary heart disease, cardiovascular and cerebrovascular diseases, migraine, pulmonary hypertension and other diseases It has a very broad development prospect. [0003] Its synthetic method generally adopts 4 or 5-methyl indole as starting material at present, protects the nitrogen on the indole ring with benzoyl, then brominates the methyl group; The ketone compound undergoes a substitution reaction; removes the benzoyl protecting group; then reacts with o-fluorobenzonitrile, and final...

Claims

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Application Information

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IPC IPC(8): C07D403/14
Inventor 陈志龙朱伟波任何严懿嘉鲍晓璐陈聃烨
Owner 陈志龙