Method for preparing zafirlukast important intermediate

A compound, the technology of nitroindole, which is applied in the field of preparation of C1-C4 alkyl 3-methoxy-4-[methyl]benzoate, can solve the problems of complex operation, high cost and tediousness, and achieve High yield, low cost and strong controllability

Active Publication Date: 2011-01-26
HAINAN SHENGKE LIFE SCI RES INST
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0010] The yield reported in the literature of this method is 60%, but the yield of repeated actual operation is only about 30%, and the operation is complicated, loaded down with trivial details, and the cost is high

Method used

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  • Method for preparing zafirlukast important intermediate
  • Method for preparing zafirlukast important intermediate
  • Method for preparing zafirlukast important intermediate

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Under nitrogen protection, 16.2 g of 5-nitroindole was added to 100 ml of dichloromethane, and 50 g of anhydrous aluminum trichloride was added. The temperature was lowered to -5-0°C, and 70 ml of dichloromethane and 25.1 g of methyl 4-carbonyl chloride-3-methoxybenzoate were added dropwise. After the dropwise addition was completed, the mixture was raised to room temperature and stirred overnight. The reaction solution was slowly poured into ice water, and stirred for 0.5 hours. Separate the organic phase, wash with 3×30 ml 5% sodium bicarbonate, and dry the organic phase with anhydrous sodium sulfate. After suction filtration, the filtrate was evaporated to remove the solvent under reduced pressure, 50ml of isopropyl ether was added to stir and crystallize, and 31.8g of a yellow solid product was obtained by filtration, with a yield of 90%.

Embodiment 2

[0030] Mix 17.7 grams of 3-methoxy-4-(5-nitro-1H-indole-3-carbonyl) methyl benzoate (formula III) obtained above with 70 milliliters of ethylene glycol, and add 8.4 grams Potassium hydroxide and 10 ml of 85% hydrazine hydrate were heated to reflux for 1.5 hours, the condenser was removed, and the water was evaporated from the reaction solution. When the temperature in the reaction flask rose to 195° C., install a condenser again, and continue heating to reflux for 5 hours. After cooling to room temperature, the reaction solution was poured into 300 ml of ice water and stirred for 0.5 hour. After suction filtration, 14.4 g of a light yellow solid product was obtained, with a yield of 85%.

[0031] Accompanying drawing is the schematic diagram of the chemical structural formula of compound (I).

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Abstract

The invention relates to the preparation method of formula (I) compound 3-methoxy-4-((5-nitro-1H-indole-3-base)methyl)benzoic acid C1-C4 alkyl esters. The compound is a crucial intermediate in the preparation of zafirlukast which is a leukotriene antagonist drug.

Description

technical field [0001] The present invention relates to 3-methoxy-4-[(1-methyl-5-nitro-1H-indol-3-yl)methyl]benzoic acid C 1 ~C 4 Preparation of alkyl esters, such compounds can be used to prepare leukotriene antagonist drug zafirlukast. Background technique [0002] Zafirlukast is a leukotriene receptor antagonist drug indicated for the prevention and long-term treatment of asthma. With the continuous development of the industrialization process, the living environment of human beings has also undergone continuous changes. With the decline of air quality and hundreds of millions of smokers, the number of asthma patients in my country's big cities is also increasing. Asthma is considered one of the four chronic diseases by the world medical community, and is listed as the top ten causes of death. Therefore, the development of zafirlukast will bring better economic and social benefits, and its chemical structural formula is as follows: [0003] [0004] Zafirlukast ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/18
Inventor 杨利民
Owner HAINAN SHENGKE LIFE SCI RES INST
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