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6-trifluoromethyl pyridine-2-acetonitrile synthesis method

A technology of trifluoromethylpyridine and a synthesis method is applied in the field of synthesis of pharmaceutical intermediate-6-trifluoromethylpyridine-2-acetonitrile, can solve problems such as inability to obtain, and achieves the effects of convenient operation and good yield

Inactive Publication Date: 2014-08-27
ZUNYI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, no matter under which kind of strong basic condition (such as n-BuLi etc.), 6-trifluoromethylpyridine or 2-halo-6-trifluoromethylpyridine reacts with acetonitrile and cannot obtain target product 6 -Trifluoromethylpyridine-2-acetonitrile (or 6-trifluoromethyl-2-pyridineacetonitrile) 1

Method used

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  • 6-trifluoromethyl pyridine-2-acetonitrile synthesis method

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Embodiment 1

[0018] Embodiment 1. Preparation of 2-cyano-6-trifluoromethylpyridine 2

[0019] 2-Bromo-6-trifluoromethylpyridine (1.13 g, 5 mmol), cuprous cyanide (0.67 g, 7.5 mmol) and potassium iodide (1.25 g, 7.5 mmol) were suspended in DMF (15 mL) and heated React at 130°C for 12 h. The resulting reaction mixture was poured into a mixed solvent of ice water (100 mL) and ethyl acetate (50 mL). The solid was filtered off, and the filtrate was extracted with ethyl acetate (50 mL*3). The combined organic phases were washed with saturated brine and dried over anhydrous magnesium sulfate. Concentration gave pale yellow oil 2-cyano-6-trifluoromethylpyridine ( 2 , 0.95 g). No need for purification, it can be directly used in the next step.

Embodiment 2

[0020] Example 2. Preparation of 6-trifluoromethylpyridine-2-carboxylic acid 3

[0021] A mixture of 2-cyano-6-trifluoromethylpyridine (2, 0.95 g) and concentrated hydrochloric acid HCl (37%, 15 mL) was heated at reflux for 2 hours. After cooling, a white solid 6-trifluoromethylpyridine-2-carboxylic acid ( 3 , 0.70 g, 74%. 1HNMR (DMSO-d6): 13.69 (s, 1H), 8.24-8.31 (m, 2H), 8.10-8.14 (m, 1H).

Embodiment 3

[0022] Example 3. Preparation of 6-trifluoromethyl-2-hydroxymethylpyridine 4

[0023] 6-Trifluoromethylpyridine-2-carboxylic acid (3,382 mg, 2 mmol) was dissolved in tetrahydrofuran (20 mL) and cooled to -10 °C. The reducing agent lithium aluminum tetrahydrogen LiAlH4 (152 mg, 4 mmol) was added in portions. After the mixture was stirred for 1 h, a few drops of water were added to quench the reaction. Ethyl acetate (20 mL) was added for extraction. The organic layer was separated and dried over anhydrous magnesium sulfate. Concentrate to dryness to obtain an oily crude product ( 4 , 320 mg) was used directly in the next step.

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Abstract

The invention provides a 6-trifluoromethyl pyridine-2-acetonitrile synthesis method. According to the 6-trifluoromethyl pyridine-2-acetonitrile synthesis method, 2-bromine-6-trifluoromethyl pyridine serves as raw materials, and a target product 1 is obtained through five steps of the cyano nucleophilic substitution reaction, the hydrolysis reaction, the reduction reaction, the sulphonate formation reaction, the cyano nucleophilic substitution reaction, wherein the reaction route is seen in the figure. According to the route of the synthesis method, the adopted raw materials are easy to obtain, the steps are convenient to operate, the yield is better, and the method is very suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a synthesis method of a pharmaceutical intermediate-6-trifluoromethylpyridine-2-acetonitrile. Background technique [0002] Pyridine-2-acetonitrile is an important pharmaceutical intermediate, and the introduction of fluorine atoms or fluorine-containing groups on aromatic rings such as benzene rings and pyridine rings is also common for drug modification to change pharmacological activities such as drug efficacy and side effects s method. Trifluoromethyl is a strong electron-withdrawing group containing three fluorine atoms. The introduction of trifluoromethyl into drug molecules sometimes has unexpected good effects. Therefore, we intend to introduce a trifluoromethyl group at the 6-position of pyridine-2-acetonitrile, laying the foundation for the development of related new drugs. [0003] Regarding the synthesis of 6-trifluoromethylpyridine-2-acetonitrile 1, th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/57
CPCC07D213/57
Inventor 王先恒李晓飞赵长阔
Owner ZUNYI MEDICAL UNIVERSITY
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