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Method for preparing 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-formaldehyde

A technology of benzopyran and dihydro, applied in the field of preparation of 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carbaldehyde, can solve the problem of harsh conditions, complex operation, reagent Risk and other problems, to achieve the effect of mild reaction conditions, cheap and easy to obtain reagents

Inactive Publication Date: 2012-01-25
SHANGHAI SHYNDEC PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The reagents used in this method are relatively dangerous, and the conditions are harsh, the operation is complicated, and it is difficult to industrialize

Method used

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  • Method for preparing 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-formaldehyde
  • Method for preparing 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-formaldehyde
  • Method for preparing 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-formaldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Under nitrogen protection, 12.8ml of reducing agent (toluene solution (content 70%) of dihydrobis(2-methoxyethoxy)sodium aluminate was added in the reaction flask, 15ml of toluene was added for dilution, and the temperature was lowered to 0°C, slowly add 3.97g of equivalent morpholine dropwise to it, keep the temperature at 0-5°C, after the dropwise addition is completed, raise the temperature to room temperature, and after 4 hours of reaction, slowly add the reaction solution dropwise to the raw material 6-fluoro -3,4-dihydro-2H-1-benzopyran-2-methyl ester 8.0g in 40ml toluene solution, the temperature is raised during this process, and the temperature is maintained at -15~-5°C. After the dropwise addition is completed, the reaction 4 hour, the reaction solution was added to 60ml of ice-water solution, stirred for 15 minutes, and the liquid was separated. The organic layer was washed twice with 50ml of salt water. After the liquid separation, the organic layer was dried...

Embodiment 2

[0023] Under nitrogen protection, 8.0ml of reducing agent (toluene solution of dihydrobis(2-methoxyethoxy)sodium aluminate (content 70%) was added in the reaction flask, 10ml of toluene was added for dilution, and the temperature was lowered to 0°C, slowly add 2.03g of tetrahydropyrrolidine equivalent to it dropwise, maintain the temperature at 0-5°C, after the dropwise addition, raise the temperature to room temperature, and slowly add the reaction solution dropwise to the raw material 6 after 4 hours of reaction -Fluoro-3,4-dihydro-2H-1-benzopyran-2-ethyl ester 5.0g in 30ml of toluene solution, the temperature is raised during this process, and the temperature is maintained at -15--5°C. After the dropwise addition is completed, After reacting for 4 hours, the reaction solution was added to 50 ml of ice-water solution, stirred for 15 minutes, and separated. The organic layer was washed twice with 400 ml of salt water. After the liquid separation, the organic layer was dried an...

Embodiment 3

[0025] Under nitrogen protection, 8.0ml of reducing agent (toluene solution of dihydrobis(2-methoxyethoxy)sodium aluminate (content 70%) was added in the reaction flask, 10ml of toluene was added for dilution, and the temperature was lowered to 0°C, slowly add 1.74g of isopropanol equivalent to it dropwise, maintain the temperature at 0-5°C, after the dropwise addition, raise the temperature to room temperature, and slowly add the reaction solution dropwise to the raw material 6- Fluorine-3,4-dihydro-2H-1-benzopyran-2-methyl ester 5.0g in 40ml toluene solution, the temperature is raised during this process, and the temperature is maintained at -15--5°C. After the dropwise addition is completed, the reaction After 6 hours, the reaction solution was added to 40 ml of ice-water solution, stirred for 15 minutes, and separated. The organic layer was washed twice with 30 ml of salt water. After the liquid separation, the organic layer was dried and evaporated to dryness to obtain the...

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Abstract

The invention relates to a method for preparing a key intermediate of a medicine for treating cardiovascular disease. The method for preparing 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-formaldehyde comprises the following steps of: adding a reducing agent, namely sodium dihydrobis(2-methoxyethoxy)aluminate which is subjected to passivation treatment into a compound shown as a formula 2, and reacting to obtain a target product 1, wherein R is C1-C5 alkyl. Compared with the conventional preparation method, the preparation method has the advantages that: a reagent is cheap and readily obtained, reaction conditions are mild, and the method is more suitable for industrialized production.

Description

technical field [0001] The invention relates to the technical field of a preparation method of a key intermediate 6-fluoro-3,4-dihydro-2H-1-chromene-2-carbaldehyde, which is a drug for treating cardiovascular diseases. Background technique [0002] Nebivolol is a potent and selective third-generation beta-blocker that increases nitric oxide levels and has vasodilation effects. As a new antihypertensive drug, nebivolol has the advantages of strong antihypertensive effect, convenient administration (once a day, one tablet each time), less adverse reactions, etc. It is mainly used for mild to moderate hypertension The treatment of patients can also be used for the treatment of angina pectoris and congestive heart failure. It is of great significance to the process research of the drug. 6-Fluoro-3,4-dihydro-2H-1-benzopyran-2-carbaldehyde is a key intermediate in the synthesis of nebivolol, and its structure is shown in 1: [0003] [0004] European patent EP334429 uses the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/58
Inventor 李春刚孙一平侯建党祥玉
Owner SHANGHAI SHYNDEC PHARMA CO LTD
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