5-bromo-7-trifluoromethyl quinoline synthetic method

A technology of trifluoromethylquinoline and synthesis method, applied in the direction of organic chemistry, etc., to achieve the effects of reasonable process selection, convenient operation and post-treatment, and simple and easy-to-obtain raw materials

Active Publication Date: 2018-08-17
SUZHOU KANGRUN PHARMA
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of this, the technical problem to be solved in the present invention is to overcome the defects of the prior art and provide a synthetic method of 5-bromo-7-trifluoromethylquinoline, the synthetic route of the synthetic method is simple, the process se

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  • 5-bromo-7-trifluoromethyl quinoline synthetic method

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preparation example Construction

[0024] like figure 1 As shown, the synthetic method of formula VII provided by the present invention: 5-bromo-7-trifluoromethylquinoline comprises the following steps:

[0025] The synthesis of step (1) 7-trifluoromethylquinoline:

[0026] The raw material m-trifluoromethylaniline (formula I) is subjected to Skraup condensation to obtain 7-trifluoromethylquinoline (formula II);

[0027] Synthesis of step (2) 5-bromo-7-trifluoromethylquinoline:

[0028] The 7-trifluoromethylquinoline (formula II) obtained in step (1) is subjected to a bromination reaction to obtain 5-bromo-7-trifluoromethylquinoline (formula III).

[0029] In other words, the synthetic method of 5-bromo-7-trifluoromethylquinoline provided by the present invention mainly comprises the following steps:

[0030] First, use m-trifluoromethylaniline as a raw material to obtain 7-trifluoromethylquinoline through Skraup condensation, and then obtain the obtained 7-trifluoromethylquinoline through bromination reacti...

Embodiment 1

[0040] The first step reaction is a Skraup condensation reaction, the reactants are m-trifluoromethylaniline and glycerol, the reaction solvent is sulfuric acid, the reaction temperature is 135°C, and the reaction time is 4h.

[0041] The second step reaction is bromination reaction, the reagent used is N-bromosuccinimide (NBS), the reaction solvent is concentrated sulfuric acid, the reaction temperature is 70°C, and the reaction time is 4h.

Embodiment 2

[0043] Synthesis of 7-trifluoromethylquinoline

[0044] H 2 SO 4 (13.7g, 0.14mol) was slowly added to glycerin (8.63g, 0.094mol), the temperature should not exceed 70°C, then m-trifluoromethylaniline (5.00g, 0.031mol) was added, the temperature was raised to 85°C, and the reaction was carried out for 40min. Potassium iodide (0.30g, 1.80mmol), iodine (0.34g, 1.34mmol) and water (1.50mL) were added, the temperature was raised to 135°C, and the reaction was carried out for 4h. Cool to room temperature, pour into ice to quench the reaction, and filter through celite. Adjust the pH of the filtrate to 7 with ammonia water, filter with suction, and fully extract the filtrate with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate and concentrated, and the residue was subjected to column chromatography to obtain 7-trifluoromethylquinoline (3.50 g, 69%).

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Abstract

The invention provides a 5-bromo-7-trifluoromethyl quinoline synthetic method. The 5-bromo-7-trifluoromethyl quinoline synthetic method comprises the following steps of by taking m-trifluoromethylaniline as a starting material, performing Skraup condensation to obtain 7-trifluoromethyl quinoline, and then performing reaction on the 7-trifluoromethyl quinoline and NBS to obtain 5-bromo-7-trifluoromethyl quinoline. According to the 5-bromo-7-trifluoromethyl quinoline synthetic method provided by the invention, a synthetic route of the method eliminates the disadvantages of incapability of purification, low yield and the like of a product in the existing synthetic technology, and the 5-bromo-7-trifluoromethyl quinoline synthetic method has the advantages of concision in synthetic route, reasonability in technology selection, low cost in raw materials, simpleness and availability in raw materials, convenience in operation and aftertreatment, high total yield and the like.

Description

technical field [0001] The invention relates to a synthesis method of a pharmaceutical intermediate, in particular to a synthesis method of 5-bromo-7-trifluoromethylquinoline. Background technique [0002] 5-Bromo-7-trifluoromethylquinoline is an important pharmaceutical intermediate in bromoquinoline. Compared with other quinoline derivatives, it has higher reactivity. Starting from it, a series of Biologically active molecules that play an important role in antimalarial, antihypertensive and antibiotic drugs. Studies have shown that a series of compounds synthesized with this molecule as the mother nucleus have high inhibitory effect on C-jun N-terminal kinases (JNKs) (WO2010091310). JNKs is one of the mitogen-activated protein kinase (MAPK) superfamily, which is involved in various physiological processes such as embryonic development, immune response, and cell growth, differentiation, and proliferation, and also participates in many pathological processes. Studies have...

Claims

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Application Information

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IPC IPC(8): C07D215/18
CPCC07D215/18
Inventor 黄家慧徐卫良徐炜政
Owner SUZHOU KANGRUN PHARMA
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