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Process for preparing 3-iodine-6-(trifluoromethyl) imidazo [1,2-a] pyridine

A technology for the preparation of trifluoromethyl, which is applied in the field of preparation of 3-iodo-6-imidazo[1,2-a]pyridine, can solve the problems of long reaction time and expensive raw materials, and achieve short reaction time , Raw materials are easy to obtain, and are beneficial to industrial applications

Inactive Publication Date: 2017-09-01
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The technical problem to be solved in the present invention is: provide a kind of preparation technology of 3-iodo-6-(trifluoromethyl)imidazo[1,2-a]pyridine, to solve the existing technology in the preparation of 3-iodo-6 -(trifluoromethyl)imidazo[1,2-a]pyridine, the raw materials are expensive and the reaction time is long.

Method used

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  • Process for preparing 3-iodine-6-(trifluoromethyl) imidazo [1,2-a] pyridine

Examples

Experimental program
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Effect test

Embodiment 1

[0013] A. Preparation of 6-(trifluoromethyl)imidazo[1,2-a]pyridine

[0014] In a 500ml single-necked bottle, add bromoacetaldehyde diethyl acetal (30.00g, 152.2mmol), 1mol / L HCL (120mL), and ethanol (10mL), stir at room temperature for 30min, and reflux for 1h until the solution is clear. Cool to room temperature, saturated NaHCO 3 Adjust the pH value to neutral, add 2-amino-5-trifluoromethylpyridine (16.45 g, 101.5 mmol), and react at room temperature for 8 h. After the reaction was completed, ethyl acetate (100mL×3) was extracted, the organic phase was collected, the solvent was evaporated to dryness under reduced pressure, and the silica gel column (mobile phase was PE:EA=2:1) ​​was used to obtain 6-(trifluoromethyl)imidazo[ 1,2-a]pyridine yellow-brown crystal 14.71g. Yield 77.9%.

[0015] B. Preparation of 3-iodo-6-(trifluoromethyl)imidazo[1,2-a]pyridine

[0016] In a 500mL three-necked flask, 6-(trifluoromethyl)imidazo[1,2-a]pyridine (12.34g, 66.3mmol) was dissolved i...

Embodiment 2

[0019] A. Preparation of 6-(trifluoromethyl)imidazo[1,2-a]pyridine

[0020] In a 500ml single-necked bottle, add bromoacetaldehyde diethyl acetal (18.23g, 92.5mmol), 1mol / L HCL (100mL), and ethanol (10mL), stir at room temperature for 30min, and reflux for 1h until the solution is clear. Cool to room temperature, saturated NaHCO 3 Adjust the pH value to neutral, add 2-amino-5-trifluoromethylpyridine (15.00 g, 92.5 mmol), and react at room temperature for 12 h. After the reaction was completed, ethyl acetate (100mL×3) was extracted, the organic phase was collected, the solvent was evaporated to dryness under reduced pressure, and the silica gel column (mobile phase was PE:EA=2:1) ​​was used to obtain 6-(trifluoromethyl)imidazo[ 1,2-a]pyridine yellow-brown crystal 13.05g. Yield 75.8%.

[0021] B. Preparation of 3-iodo-6-(trifluoromethyl)imidazo[1,2-a]pyridine

[0022] In a 500mL three-necked flask, 6-(trifluoromethyl)imidazo[1,2-a]pyridine (10.00g, 53.7mmol) was dissolved in...

Embodiment 3

[0025] A. Preparation of 6-(trifluoromethyl)imidazo[1,2-a]pyridine

[0026] In a 500ml single-necked bottle, add bromoacetaldehyde diethyl acetal (48.63g, 246.7mmol), 1mol / L HCL (180mL), and ethanol (15mL), stir at room temperature for 30min, and reflux for 2h until the solution is clear. Cool to room temperature, saturated NaHCO 3 Adjust the pH value to neutral, add 2-amino-5-trifluoromethylpyridine (20.00 g, 123.4 mmol), and react at room temperature for 6 h. After the reaction was completed, ethyl acetate (100mL×3) was extracted, the organic phase was collected, the solvent was evaporated to dryness under reduced pressure, and the silica gel column (mobile phase was PE:EA=2:1) ​​was used to obtain 6-(trifluoromethyl)imidazo[ 1,2-a]pyridine yellow-brown crystal 18.22g. Yield 79.4%.

[0027] B. Preparation of 3-iodo-6-(trifluoromethyl)imidazo[1,2-a]pyridine

[0028] In a 500mL three-necked flask, 6-(trifluoromethyl)imidazo[1,2-a]pyridine (15.00g, 80.6mmol) was dissolved i...

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Abstract

The invention discloses a process for preparing 3-iodine-6-(trifluoromethyl) imidazo [1,2-a] pyridine. The process comprises the following steps: by taking 2-amino-5-trifluoromethyl picoline as a raw material, performing reaction with bromoacetaldehyde diethyl acetal to generate 6-(trifluoromethyl) imidazo [1,2-a] pyridine, and performing reaction on the 6-(trifluoromethyl) imidazo [1,2-a] pyridine with N-iodosuccinimide, thereby obtaining a target compound, namely 3-iodine-6-(trifluoromethyl) imidazo [1,2-a] pyridine. The process is low in price of raw materials, easy in raw material obtaining, relatively short in reaction time and beneficial to industrial application.

Description

technical field [0001] The invention relates to a preparation process of 3-iodo-6-(trifluoromethyl)imidazo[1,2-a]pyridine. It belongs to the fields of fine chemicals, pharmaceutical intermediates and materials. Background technique [0002] Imidazo[1,2-a]pyridine derivatives not only play an important role in the production of medicines, pesticides, dyes, etc., but also are one of the most common intermediates in many organic synthesis. 3-iodo-6-(trifluoromethyl)imidazo[1,2-a]pyridine is an important pyridine drug intermediate, which is often used in the synthesis of protein kinase inhibitors. Among them, the iodine at the 3-position is a good leaving group, which can further introduce various functional groups. Its mother ring has a good conjugation effect and can be used to develop new luminescent materials. [0003] At present, there are few reports on the synthesis process of 3-iodo-6-(trifluoromethyl)imidazo[1,2-a]pyridine, and the routes reported in WO2014055955 and...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 周志旭李彦青刘力
Owner GUIZHOU UNIV
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