N-2-pyrimidinyl-3-fluoroindole compound and its preparation method and application

A technology for pyrimidinyl indole and compounds, which is applied in the field of N-2-pyrimidinyl-3-fluoroindole compounds, and can solve the problems of harsh conditions, low selectivity of non-corresponding forms, low yield, etc.

Active Publication Date: 2021-10-15
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of these methods have low yields, harsh conditions, complex devices, and low selectivity to non-corresponding forms.

Method used

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  • N-2-pyrimidinyl-3-fluoroindole compound and its preparation method and application
  • N-2-pyrimidinyl-3-fluoroindole compound and its preparation method and application
  • N-2-pyrimidinyl-3-fluoroindole compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1: Preparation of N-2-pyrimidinyl-3-fluoroindole (I-1)

[0049] The reaction formula is as follows:

[0050]

[0051] Dissolve 0.058g (0.3mmol) of N-2-pyrimidinylindole (Ⅲ-1) in 1mL of acetonitrile, add 0.126g (0.36mmol) of Selectfluor (F source, purchased from Beijing Bailingwei Technology Co., Ltd.), and then add 0.010g (0.015mmol) Eosin Y (photocatalyst, purchased from Beijing Bailingwei Technology Co., Ltd.), finally add 0.017g (0.09mmol) CuI (purchased from Beijing Bailingwei Technology Co., Ltd.), under the irradiation of 9w blue LED light, 25 °C React for 2.0 hours, follow the reaction by TLC, the N-2-pyrimidinyl indole (Ⅲ-1) point disappears, the reaction is complete, dilute with 10mL ethyl acetate, wash 3 times with 10ml saturated aqueous sodium chloride solution, collect the organic phase, and use Dry over anhydrous sodium sulfate and concentrate to obtain the crude product containing (I-1), which is separated by thin-layer chromatography (with a m...

Embodiment 2～9

[0053] Embodiment 2~9 substituent screening:

[0054] R in formula (V), (VI) 3 For tert-butoxycarbonyl, pivaloyl, benzyl, acetyl, benzoyl, H, methyl.

Embodiment 2

[0056] Dissolve 0.065g (0.3mmol) N-tert-butoxycarbonylindole (VI-1, purchased from Beijing Bailingwei Technology Co., Ltd.) in 1mL acetonitrile, add 0.126g (0.36mmol) Selectfluor (F source), and then add 0.010g (0.015mmol) eosin Y (photocatalyst), finally add 0.017g (0.09mmol) CuI, under the irradiation of 9w blue LED lamp, react at 25°C for 4.0 hours, follow the reaction by TLC, N-tert-butoxycarbonylindole ( VI-1) point disappears, producing a lot of by-products. The reaction solution was diluted with 10 mL of ethyl acetate, washed 3 times with 10 mL of saturated aqueous sodium chloride solution, the organic phase was collected, dried over anhydrous sodium sulfate, and concentrated to obtain the crude product (V-1), which was used on a large plate of thin layer chromatography (with The mixture of petroleum ether and ethyl acetate with a volume ratio of 25:1 is used as a developing solvent) to separate, collect the silica gel powder containing the target compound, and use a mi...

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Abstract

A preparation method of N-2-pyrimidinyl-3-fluoroindole compound shown in formula (I), described method comprises the following steps: take acetonitrile solvent as reaction medium, add N shown in formula (III) ‑2‑pyrimidinyl indole compound, selectfluor, CuI and photocatalyst, react at room temperature under blue light irradiation for 2 to 5 hours, after the reaction is complete, the resulting reaction mixture is post-processed to obtain N‑2‑pyrimidinyl represented by formula (I) ‑3‑fluoroindoles. This type of compound is a kind of inhibitor compound that can significantly inhibit the activity of monoamine oxidase, especially I-2 and I-3 have high selectivity to MAO-A, which provides a research basis for the screening of antidepressant and anti-Parkinson drugs . The invention uses a photocatalyst to react under blue light irradiation and room temperature, has mild reaction conditions, high site selectivity, high reaction efficiency, greenness and environmental protection, and the reaction yield can reach 85%.

Description

technical field [0001] The invention relates to an N-2-pyrimidinyl-3-fluoroindole compound and its preparation and application. Background technique [0002] Monoamine oxidase (monoamine oxidase, MAO) is a naturally occurring enzyme in the human body, which can catalyze the oxidative deamination reaction of monoamines. There are two types of MAO in the human body: MAO A and MAO B. Monoamine oxidase inhibitors can inhibit the oxidation activity of monoamine oxidase to monoamines, so as to reduce or eliminate the diseases caused by the reduction of monoamines or the high activity of monoamine oxidase caused by various reasons. [0003] Monoamine oxidase inhibitors are mainly divided into three types. The first type is non-selective monoamine oxidase inhibitors, which can inhibit both monoamine oxidase A and monoamine oxidase B. This class of drugs mainly includes phenprohydrazine, phenelzine, isocarboxazid and anti-monoamine oxidase inhibitors. Phenylcypromine, etc., among w...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/04A61P25/24A61P25/16
CPCA61P25/16A61P25/24C07D403/04
Inventor 朱勍王磊
Owner ZHEJIANG UNIV OF TECH
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