Benzofuran [2, 3-c] pyridine compound and synthetic method thereof

A technology of benzofuran and a synthesis method, which is applied in the field of organic intermediate synthesis, can solve the problems of high cost, harsh reaction conditions, and limit the industrial application of such compounds, and achieves the effects of small environmental impact and low cost.

Inactive Publication Date: 2014-04-30
WUHAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned method for synthesizing benzofuro[2,3-c]pyridine compounds has complex steps and harsh reaction conditions, for example, it needs to be carried out under anhydrous and oxygen-free reaction conditions, etc.
Wen et al. used 3-chloropyridine to react with tributyltin chloride at -78°C, and the resulting product reacted with o-iodophenol under the condition of palladium chloride to generate intermediate 2-(3-chloropyridine-4 -yl) phenol, the intermediate is cyclized under the catalysis of tert-butyl sodium to obtain be

Method used

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  • Benzofuran [2, 3-c] pyridine compound and synthetic method thereof
  • Benzofuran [2, 3-c] pyridine compound and synthetic method thereof
  • Benzofuran [2, 3-c] pyridine compound and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis of 3-methyl-1-phenyl-benzofuro[2,3-c]pyridine:

[0030] Weigh 2g of α-bromoacetophenone (10mmol), 1.21g of 4-(2-hydroxyphenyl)-3-buten-2-one (7.5mmol) and 630mg of potassium hydroxide (11.25mmol), add to 40mL of tetrahydrofuran , and the reaction was stirred at 25°C, and the reaction was tracked by thin-layer chromatography. After 1 hour of reaction, 6.1g of ammonium acetate (80mmol) and 80mL of absolute ethanol were added to the system, and the reaction was continued for 3 hours under reflux and stirring, and the reflux temperature was 100°C , the resulting reaction mixture was removed by vacuum distillation to remove the solvent, and then the remaining material was purified with a silica gel column to obtain a light yellow solid product, weighing 1.37g, with a yield of 74%.

[0031] Adopt nuclear magnetic resonance (NMR) method to test the product prepared in this embodiment, such as figure 1 with figure 2 , are respectively the product obtained in this e...

Embodiment 2

[0036] Synthesis of 3-methyl-1-phenyl-benzofuro[2,3-c]pyridine: the same method as in Example 1 was adopted, except that acetonitrile was used instead of tetrahydrofuran, and the results obtained were basically the same as in Example 1.

Embodiment 3

[0038] Synthesis of 1-(3-bromophenyl)-3-methyl-benzofuro[2,3-c]pyridine:

[0039] Weigh 2.77g 2,3'-dibromoacetophenone (10mmol), 1.21g 4-(2-hydroxyphenyl)-3-buten-2-one (7.5mmol) and 630mg potassium hydroxide (11.25mmol), Add 40mL of tetrahydrofuran, and stir the reaction at 25°C, follow the reaction by thin-layer chromatography, after 2.5h of reaction, add 6.1g of ammonium acetate (80mmol) and 100mL of absolute ethanol to the system, continue to reflux and stir for 3 hours, The reflux temperature was 100°C, and the resulting reaction mixture was distilled under reduced pressure to remove the solvent, and then the remaining substance was purified with a silica gel column to obtain a pale yellow solid product weighing 1.17 g with a yield of 46%.

[0040] Adopt the method identical with embodiment one to test the product prepared in this embodiment, as image 3 with Figure 4 , are respectively the product obtained in this example 1 H NMR spectrum and 13 C NMR spectrum, its ...

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PUM

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Abstract

The invention relates to a benzofuran [2, 3-c] pyridine compound and a synthetic method thereof. The benzofuran [2, 3-c] pyridine compound has a general formula shown in the specification, wherein R1 is phenyl, 3-bromo-phenyl, 4-bromo-phenyl, 4-chloro-phenyl, 4-methoxy-phenyl, 3-methyl-phenyl or 4-methyl-phenyl; R2 is hydrogen or 5-chlorine, 5-bromine, 5-tert-butyl, 3,5-ditert-butyl, 4-methoxy, 5-methoxy, 5-methyl, 3,5-dimethyl and 4,5-dimethyl; R3 is methyl or phenyl, 4-bromo-phenyl, 3-bromo-phenyl, 2-chloro-phenyl, 4-chloro-phenyl, 4-methoxy-phenyl and 4-methyl-phenyl. According to the synthetic method disclosed by the invention, alpha-bromoacetophenone or a derivative thereof as well as 4-(2-hydroxyphenyl)-3-butylene-2-ketone or a derivative thereof are used as reactants, and a one-pot method is adopted to synthesize the benzofuran [2, 3-c] pyridine compound. The synthetic method is simple and convenient in step, mild in condition and high in yield.

Description

technical field [0001] The invention belongs to the technical field of synthesis of organic intermediates, in particular to benzofuro[2,3-c]pyridine compounds and a synthesis method thereof. Background technique [0002] Benzofuro[2,3-c]pyridine organic heterocyclic compounds are widely used in organic synthesis, medicine and other fields, and are important pharmaceutical intermediates. In addition, many molecules with physiological activity also contain such structural units. For example, D.G. Wishka et al. synthesized a benzofuro[2,3-c]pyridine compound (I), which is a central nervous system active drug (WO02 / 100857A1); L.A.Gharat et al. synthesized benzofuro[2,3-c]pyridine compound (II), which is an inhibitor of phosphodiesterase-10 (WO2011 / 132051A2). The above-mentioned method for synthesizing benzofuro[2,3-c]pyridine compounds has complicated steps and harsh reaction conditions, for example, it needs to be carried out under anhydrous and oxygen-free reaction conditio...

Claims

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Application Information

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IPC IPC(8): C07D491/048C07D519/00
CPCC07D491/048C07D519/00
Inventor 郑化胡佳兴张方林徐文刚陈小清李青翠张津甫武博王宝龙
Owner WUHAN UNIV OF TECH
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