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Synthesis method of (3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-yl)methanol

A synthetic method, 3-b technology, applied in organic chemistry, etc.

Active Publication Date: 2020-01-24
CHENGDU CHEMPARTNER
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no report on the synthesis method of (3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-yl)methanol compound in the prior art

Method used

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  • Synthesis method of (3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-yl)methanol
  • Synthesis method of (3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-yl)methanol
  • Synthesis method of (3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-yl)methanol

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Experimental program
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Effect test

Embodiment 1

[0080] The preparation of embodiment 1,6-chloro-5-iodonicotinic acid methyl ester

[0081]

[0082] Add 25mL of phosphorus oxychloride and 5.0g of methyl 6-hydroxy-5-iodonicotinate into the reaction vessel, heat up to 80°C and stir for 4 hours; the reaction solution is cooled to room temperature, and the reaction is quenched by adding ice water, Ethyl acetate was added for extraction, the organic phase was washed, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated and purified by column chromatography to obtain compound 6-chloro-5-ionicotinic acid methyl ester (A-2) (5.2 g of white solid, yield rate 98%).

Embodiment 2

[0083] Embodiment 2, the preparation of 5-(3-(tert-butyldimethylsilyloxy)prop-1-ynyl)-6-chloronicotinic acid methyl ester

[0084]

[0085] Add 5.0 g of 6-chloro-5-iodonicotinic acid methyl ester, 3.5 g of tert-butyldimethyl (prop-2-ynyloxy) silane, 0.93 g of bistriphenylphosphine di Palladium chloride, 0.35g of cuprous iodide, 25ml of tetrahydrofuran and 4.5g of triethylamine, the reaction system was replaced with nitrogen, and stirred at room temperature for 4 hours; Analysis and purification gave compound 5-(3-(tert-butyldimethylsilyloxy)prop-1-ynyl)-6-chloronicotinic acid methyl ester (A-4) (brown oily liquid, 4.2g, Yield 74%).

Embodiment 3

[0086] Embodiment 3, the preparation of 5-(3-(tert-butyldimethylsilyloxy) propyl)-6-chloronicotinic acid methyl ester

[0087]

[0088] Add 3.5 g of 5-(3-(tert-butyldimethylsilyloxy) prop-1-ynyl)-6-chloronicotinic acid methyl ester, 0.5 g of platinum dioxide and 30 ml ethyl acetate, the reaction system was replaced by hydrogen, and stirred at room temperature for 1 hour; Siloxy)propyl)-6-chloronicotinic acid methyl ester (A-5) (colorless oily liquid, 2.4 g, yield 68%).

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Abstract

The invention discloses a synthesis method of a (3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-yl)methanol compound. Methyl 6-hydroxy-5-iodonicotinate which is used as an initial raw material undergoes a chlorination reaction, and the obtained reaction product and tert-butyl dimethyl(prop-2-alkynyloxy)silane undergo an alkyne substitution reaction, an alkynyl reduction reaction, a TBS protection removal reaction, a cyclization reaction and reduction to obtain the target compound. The synthesis method of the (3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-yl)methanol fills the blank of synthesis methods in theprior art, and the method adopting the above whole synthesis route has the advantages of good step repeatability, high conversion rate, high yield, easiness in purification, mild reaction conditions,high safety, greenness and environmental friendliness; and the obtained 4-fluoro-3-substituted-pyridine-2-formate product compound has the advantages of high purity, good quality, and facilitation ofrealization of industrialization.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing (3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-yl)methanol. Background technique [0002] Dopamine receptor D4 is a G protein-coupled receptor encoded by the DRD4 gene. Like other dopamine receptor subtypes, D4 receptors are activated by the neurotransmitter dopamine. It is associated with many neurological or psychological conditions such as schizophrenia, Parkinson's disease, bipolar disorder, addictive behavior, and eating disorders nervosa such as anorexia, bulimia, and binge eating disorder. Dopamine receptors are also the target of many treatments for schizophrenia and Parkinson's disease. Dopamine receptor agonists are a class of drugs that are similar to dopamine in molecular conformation and can directly act on dopamine receptors to increase dopaminergic stimulation and restore a balanced state. With the further study of its pharmacological...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/052
CPCC07D491/052
Inventor 林森牟韬袁婷白峰
Owner CHENGDU CHEMPARTNER
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