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Preparation method of 5-methoxy-1H-pyrrolo(3,2-b)pyridine-1-formic acid

A methoxy, 2-b technology, applied in the fields of organic synthesis and chemical pharmacy, can solve the problems of being inflammable and explosive, unsuitable for industrial production, expensive, etc., and achieves easy post-processing, less by-products, and safety. Good results

Inactive Publication Date: 2010-07-14
SUZHOU HEALTH COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this preparation method, the first step needs to use tetrakis (triphenylphosphine) palladium and trimethylboroxine, these two reagents are more expensive and are not suitable for industrial production
In the second step reaction, diethyl ether is used as a solvent, which is flammable and explosive, and is not suitable for industrial production.

Method used

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Embodiment Construction

[0009] The present invention will be described in further detail below in combination with specific embodiments.

[0010] A preparation method of 5-methoxy-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid, comprising the steps of:

[0011] 1) Synthesis of 2-methyl-6-methoxy-3-nitropyridine;

[0012] In a 500mL three-necked flask, add 150mL of methanol, and under mechanical stirring, add 5.0g (0.215mol) of sodium flakes; after all the sodium has reacted, add 20g (0.116mol) of 2-methyl-6-chloro-3-nitropyridine ), stirred at room temperature for 4 hours; the reaction solution was poured into 100 g of ice water and stirred to precipitate out; the filter cake was washed with water 3 times, 20 mL each time, to obtain a crude product; recrystallized with ethyl acetate. 12.7 g of fine product was obtained, which was a yellow-white solid, which was 2-methyl-6-methoxy-3-nitropyridine.

[0013] 2) Synthesis of ethyl 3-(6-methoxy-3-nitropyridin-2-yl)-2-oxopropionate;

[0014] In a 500mL thr...

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Abstract

The invention discloses a preparation method of 5-methoxy-1H-pyrrolo(3,2-b)pyridine-1-formic acid, which is safe, has easy post-processing and good product quality and is suitable for the preparation in industrial production. The preparation method comprises the following steps of:, synthesizing by Williamson by using 2-methoxy-6-chlor-3-nitropyridine as a raw material, preparing 2-methoxy-6-methoxyl-3-nitropyridine by using cheaper sodium methylate, then preparing a compound of 5-methoxyl-1H-pyrrolo(3,2-b)pyridine-2-ethyl formate by using a Reissert synthetic method, and finally preparing a final product of the 5-methoxy-1H-pyrrolo(3,2-b)pyridine-1-formic acid by hydrolysis.

Description

technical field [0001] The present invention relates to the fields of organic synthesis and chemical pharmacy, in particular to a 5-methoxy-1H-pyrrole prepared from 2-methyl-6-chloro-3-nitropyridine through Williamson synthesis, Reissert synthesis and hydrolysis And the preparation method of [3,2-b] pyridine-2-carboxylic acid. Background technique [0002] 5-methoxy-1H-pyrrolopyridine-2-carboxylic acid is an important raw material in organic synthesis, and its derivative pyrrolopyridine-2-carboxylic acid amide is a glycogen phosphorylase inhibitor , can be used for preventing or treating diabetes, hypertension, hypercholesterolemia, hyperinsulinemia, hyperlipidemia, hypertension, atherosclerosis or tissue ischemia, and can be used as a cardioprotective agent. [0003] In the existing method for preparing 5-methoxyl-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid, 2-chloro-6-methoxyl-3-nitropyridine is used as raw material, through Methylation yields 2-methyl-6-methoxy-3-nitrop...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
Inventor 张立光叶蓓
Owner SUZHOU HEALTH COLLEGE