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Preparation method of 4-methoxyl pyrrole intermediate

A technology of methoxypyrrole and intermediates, which is applied in the field of chemical drug synthesis, can solve the problems of inaccessibility of starting materials, inability to carry out large-scale production, high price and the like

Pending Publication Date: 2019-06-11
NANJING GEAR PHARMA & TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0022] The starting materials of this route are not easy to obtain, expensive, and cannot be mass-produced

Method used

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  • Preparation method of 4-methoxyl pyrrole intermediate
  • Preparation method of 4-methoxyl pyrrole intermediate
  • Preparation method of 4-methoxyl pyrrole intermediate

Examples

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Embodiment Construction

[0026] The following examples can enable those skilled in the art to understand the present invention more comprehensively, but the present invention is not limited to the scope of the described examples.

[0027] 1. Synthesis of (III): Get 75g (I), 108g formamide, 3.35g camphorsulfonic acid, and 75g (II) into the reaction flask. Stir in an oil bath under nitrogen protection and raise the temperature to 65-70°C and stir for 16h. Cool to room temperature (15-30°C), add 300ml of water, stir for 30min, and filter. The filter cake was rinsed 3 times with 50ml of water. Scoop out the filter cake. Add 200ml of methanol, stir at room temperature 15-30°C for 30min and then filter. Add 200ml of methanol to the filter cake, stir at room temperature 15-30°C for 30min, and then filter. After the filter cake was dried, 117 g of white powder were obtained. Yield 75%.

[0028] 2. Synthesis of (IV): Dissolve 68.2g of (III), 680ml of anhydrous tetrahydrofuran, and add 64.28g of phosphoru...

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Abstract

The invention provides a preparation method of a 4-methoxyl pyrrole intermediate. The preparation method comprises the following steps: (1) carrying out a reaction on a compound 2,4-difluorobenzaldehyde represented as in a formula (I) with a compound p-toluenesulfonic acid represented in a formula (II) under a condition of an alkaline solvent and acid catalysis to obtain a compound represented asin a formula (III); (2) carrying out a reaction on the compound represented as in the formula (III) with a compound phosphorus oxychloride in the presence of an alkali to obtain a compound representedas in a formula (IV); and (3) carrying out a reaction on the compound represented as in the formula (IV) with a compound 2-(methoxymethylene)dimethyl malonate represented as in a formula (V) to obtain a compound (4-methoxyl pyrrole intermediate) represented as in a formula (AB03288). According to the method, the raw materials for preparing the 4-methoxy pyrrole intermediate are easy to obtain, the reaction conditions of all the steps are mild, purification is easy, operation is simple, and the yield is high.

Description

technical field [0001] The invention belongs to the technical field of chemical drug synthesis and relates to a preparation method of 5-(2,4-difluorophenyl)-4-methoxy-1H-pyrrole-3-carboxylic acid methyl ester. Background technique [0002] When the balance between the human body's attack factors (such as gastric acid, Helicobacter pepsin, stress, alcohol and tobacco, etc.) and defense factors (such as gastric mucosa, bicarbonate, prostaglandins, blood supply, etc.) is disrupted, Gastrointestinal ulceration, gastritis, and reflux esophagitis have occurred while balancing offensive factors (eg, gastric acid, acidobacteria, stress, alcohol, tobacco, etc.) and defensive factors (eg, gastric mucosa, bicarbonate, prostaglandins) , the degree of blood supply, etc.) is destroyed. Therefore, therapeutic agents for treating gastrointestinal injuries such as gastrointestinal ulcers, gastritis, and reflux esophagitis are classified into drugs for suppressing aggressive factors and drug...

Claims

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Application Information

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IPC IPC(8): C07D207/36
Inventor 姜洪建房远飞周建邵志强
Owner NANJING GEAR PHARMA & TECH CO LTD
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