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Preparation method of flurbiprofen or flurbiprofen axetil

A technology of flurbiprofen axetil and flurbiprofen, which is applied in the field of preparation of flurbiprofen or flurbiprofen axetil, can solve the problem of inability to balance reaction regioselectivity and yield, and achieve high molar yield Effect

Pending Publication Date: 2022-06-21
ZHEJIANG NHU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The selectivity and yield of the reaction region of this synthetic method cannot be balanced, and about 40 mol% of isomers will be produced

Method used

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  • Preparation method of flurbiprofen or flurbiprofen axetil
  • Preparation method of flurbiprofen or flurbiprofen axetil
  • Preparation method of flurbiprofen or flurbiprofen axetil

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preparation example Construction

[0029] The preparation method of flurbiprofen or flurbiprofen axetil provided by the invention comprises:

[0030] S1, the first raw material, the second raw material, the palladium catalyst, the co-catalyst and the organic solvent are mixed to obtain a mixture, wherein the first raw material is 2-(2-fluoro-4-bicarbonate whose structural formula is shown in the following formula (1). benzene) haloethane, the second raw material is water or alcohol, and the cocatalyst includes at least one of magnesium and zinc;

[0031]

[0032] S2, feed the reaction gas containing carbon monoxide into the mixture, and carry out a heating reaction to obtain the flurbiprofen or flurbiprofen axetil whose structural formula is shown in the following formula (2),

[0033]

[0034] Wherein, X in formula (1) is selected from a halogen atom, and R in formula (2) is selected from hydrogen atom or an alkyl group, and the alkyl group is a group obtained by removing the hydroxyl group of the alcoho...

Embodiment 1

[0053] In the autoclave, put into 3.5 mg of palladium chloride, 1.4 mg of magnesium, 10.4 mg of triphenylphosphine, 16.66 g (59.7 mol) of 2-(2-fluoro-4-biphenyl) bromoethane, 3.22 g of water and toluene 15mL. After capping, carbon monoxide (CO) was used to replace the air in the autoclave, so that the atmosphere in the autoclave was a carbon monoxide atmosphere.

[0054] Then use a booster pump to fill the autoclave with carbon monoxide gas to stabilize the internal pressure at about 10.0MPa, then place the autoclave in an oil bath, stir and heat to raise the temperature to 130°C, and the reaction process automatically controls the internal pressure at 14.0MPa- 15.0MPa, after the reaction is completed, the temperature is lowered to below 30 ° C, the reaction kettle cover is opened after the pressure is released, and the reaction product is obtained, and the reaction product is filtered and concentrated and then added with dichloromethane (CH 2 Cl 2 ) was dissolved, washed wit...

Embodiment 2

[0056] In the autoclave, put into 10.5 mg of palladium chloride, 1.4 mg of magnesium, 31.3 mg of triphenylphosphine, 16.65 g (59.7 mol) of 2-(2-fluoro-4-biphenyl) bromoethane, 3.22 g of water and toluene 15mL. After capping, carbon monoxide (CO) was used to replace the air in the autoclave, so that the atmosphere in the autoclave was a carbon monoxide atmosphere.

[0057] Then use a booster pump to fill the autoclave with carbon monoxide gas to stabilize the internal pressure at about 10.0MPa, then place the autoclave in an oil bath, stir and heat to raise the temperature to 130°C, and the reaction process automatically controls the internal pressure at 14.0MPa- 15.0MPa, after the reaction is completed, the temperature is lowered to below 30 ° C, the reaction kettle cover is opened after the pressure is released, and the reaction product is obtained, and the reaction product is filtered and concentrated and then added with dichloromethane (CH 2 Cl 2 ) was dissolved, washed wi...

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Abstract

The invention relates to a preparation method of flurbiprofen or flurbiprofen axetil. The preparation method comprises the following steps: mixing 2-(2-fluoro-4-biphenyl) halogenated ethane, water or alcohol, a palladium catalyst, a cocatalyst and an organic solvent to obtain a mixture; and introducing a reaction gas containing carbon monoxide into the mixture, and carrying out a heating reaction to obtain flurbiprofen or flurbiprofen axetil. The flurbiprofen or flurbiprofen axetil prepared by the method is high in yield, the molar yield can reach 95.4%, and the product purity can reach 99.5%.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of flurbiprofen or flurbiprofen axetil. Background technique [0002] Flurbiprofen, also known as fenfluibuprofen and fluorobiphenylpropionic acid, is a potent phenylpropionic acid antipyretic, anti-inflammatory and analgesic drug, which can inhibit prostaglandin synthesis of cyclooxygenase and cause pain relief and anti-inflammatory effects. and antipyretic effect. Among them, the anti-inflammatory effect and analgesic effect are 250 times and 50 times that of aspirin respectively, which are stronger than ibuprofen and have lower toxicity. , Mainly used for rheumatoid arthritis, rheumatoid arthritis, ankylosing spondylitis, degenerative arthritis and so on. [0003] Patent US3755427A and literature DrugsFut., 1976,1,7,323 introduced the classical organic synthesis method of flurbiprofen, specifically: starting from 4-bromo-3-nitroacetophenone, th...

Claims

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Application Information

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IPC IPC(8): C07C67/36C07C69/65C07C51/10C07C57/58
CPCC07C67/36C07C51/10C07C69/65C07C57/58
Inventor 王锦金杨灿潮方向胡瑞君胡鑫鹦宋聪
Owner ZHEJIANG NHU CO LTD
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