Benzofuro[2,3-c]pyridine compound and its synthesis method
A benzofuran and synthetic method technology, applied in the field of organic intermediate synthesis, can solve the problems of high cost, harsh reaction conditions, complex process, etc., and achieve the effect of low cost, small environmental impact, and simple process
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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 and figure 2 , are respectively the product obtained in this ex...
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 and Figure 4 , are respectively the product obtained in this example 1 HNMR spectrum and 13 CNMR spectrum, its 1 ...
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