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Synthesis method for 6-fluoroimidazo[1, 2-a]pyridine-3-phenyl ketone

A synthetic method, 2-a technology, applied in the direction of organic chemistry, etc., can solve the problems of high market price, difficult synthesis, lack of literature and patent reports, etc., and achieve the effects of easy promotion, simple post-processing, and stable product quality

Inactive Publication Date: 2015-08-12
SHANDONG YOUBANG BIOCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This product has great value, its synthesis is difficult, the market price is expensive, lack of literature and related patent reports

Method used

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  • Synthesis method for 6-fluoroimidazo[1, 2-a]pyridine-3-phenyl ketone

Examples

Experimental program
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Effect test

Embodiment 1

[0027] 80mL (71.7g, 600mmol) of N,N-dimethylformamide dimethyl acetal is both solvent and reaction raw material, react with 2-amino-5-fluoropyridine (22.4g, 200mmol) at 40°C for 3 hours, After the reaction, N,N-dimethyl-N'-2-(5-fluoro-pyridinyl)-formamidine intermediate is obtained, and the excess N,N-dimethylformamide dimethyl acetal is removed by rotary evaporation , add 120 ml (125 g) dioxane, NaHCO 3 (25.2g, 300mmol) and α-bromoacetophenone (59.7g, 300mmol), reacted at 100°C for 12 hours, after the reaction was completed, cooled to room temperature, placed in the freezer for 3 hours, and suction filtered to obtain 24.5g of high purity Crystals of 6-fluoroimidazo[1,2-a]pyridine-3-phenylone. Add 600 ml of water and 200 ml of ethyl acetate to the mother liquor for extraction, separate the organic phase, extract the aqueous phase with ethyl acetate (3×200 ml), combine the organic phases, wash with water (2×150 ml), and add 200 ml of saturated saline Wash, anhydrous Na 2 SO...

Embodiment 2

[0029] 80mL (71.7g, 600mmol) of N,N-dimethylformamide dimethyl acetal is both a solvent and a reaction material, reacted with 2-amino-5-fluoropyridine (22.4g, 200mmol) at 80°C for 6 hours, After the reaction, N,N-dimethyl-N'-2-(5-fluoro-pyridinyl)-formamidine intermediate is obtained, and the excess N,N-dimethylformamide dimethyl acetal is removed by rotary evaporation , add 120 ml (125 g) dioxane, NaHCO 3 (25.2g, 300mmol) and α-bromoacetophenone (47.76g, 240mmol), react at 120°C for 8 hours, after the reaction is completed, cool to room temperature, place in the freezer for 3 hours, and filter with suction to obtain 24g of high-purity Crystals of 6-fluoroimidazo[1,2-a]pyridine-3-phenylone. Add 600 ml of water and 200 ml of ethyl acetate to the mother liquor for extraction, separate the organic phase, extract the aqueous phase with ethyl acetate (3×200 ml), combine the organic phases, wash with water (2×150 ml), and add 200 ml of saturated saline Wash, anhydrous Na 2 SO 4D...

Embodiment 3

[0031] 80mL (71.7g, 600mmol) of N,N-dimethylformamide dimethyl acetal is both a solvent and a reaction raw material, react with 2-amino-5-fluoropyridine (22.4g, 200mmol) at 100°C for 3 hours, After the reaction, N,N-dimethyl-N'-2-(5-fluoro-pyridinyl)-formamidine intermediate is obtained, and the excess N,N-dimethylformamide dimethyl acetal is removed by rotary evaporation , add 120 ml (125g) DMF, sodium hydroxide (12g, 300mmol) and α-bromoacetophenone (59.7g, 300mmol), react at 160°C for 8 hours, after the reaction is completed, cool to room temperature, and place in the freezer 3 After 1 hour, it was filtered with suction to obtain 23 g of high-purity 6-fluoroimidazo[1,2-a]pyridine-3-phenylone crystals. Add 600 ml of water and 200 ml of ethyl acetate to the mother liquor for extraction, separate the organic phase, extract the aqueous phase with ethyl acetate (3×200 ml), combine the organic phases, wash with water (2×150 ml), and add 200 ml of saturated saline Wash, anhydrous...

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Abstract

The invention relates to a synthesis method for 6-fluoroimidazo[1, 2-a]pyridine-3-phenyl ketone. The method includes: reacting N-dimethylformamide dimethylacetal with 2-amino-5-fluoropyridine at 40-100DEG C to obtain an intermediate, without purification and under the action of alkali, subjecting the intermediate and alpha-bromoacetophenone to reaction in certain solvent at 60-160DEG C, at the end of reaction, performing cooling to room temperature, precipitating most high purity 6-fluoroimidazo[1, 2-a]pyridine3-phenyl ketone, adding water into mother liquor, and then carrying out extraction, washing, drying, and rotary evaporation concentration to obtain a 6-fluoroimidazo[1, 2-a]pyridine3-phenyl ketone crude product, and recrystallizing the crude product to obtain a pure product. The reaction raw materials are easily available, the prices are reasonable, the reaction conditions are mild, the method is easy to operate and control, the aftertreatment is simple, and the product has stable quality and high purity.

Description

(1) Technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for synthesizing 6-fluoroimidazo[1,2-a]pyridine-3-phenylketone. (2) Background technology [0002] Phenyl ketone derivatives are important pharmaceutical intermediates. At present, there are mainly two methods for preparing such compounds: [0003] 1. Grignard reagent method (US5104870A): 3,5-difluorobenzonitrile and alkyl Grignard reagent are reacted to prepare corresponding 3,5-difluorophenyl ketone, such as 3,5-difluorobenzonitrile After reacting with Grignard reagent ethylmagnesium bromide, it is hydrolyzed to prepare 3,5-difluoropropiophenone. The reaction conditions of this method are mild and the operation is relatively simple, but the raw material 3,5-difluorobenzonitrile is expensive, and the solvent used in the reaction Diethyl ether with a low boiling point is more dangerous to use it as a solvent for large-scale production. At the same time, ...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 崔淑芬韩猛来新胜耿宣平曹惊涛
Owner SHANDONG YOUBANG BIOCHEM TECH
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