反应详情

温度

110 °C

In an oven-dried flask, combine 4-bromo-1-methyl-1H-imidazole (0.200 g, 1.24 mmol), copper (I) iodide (0.022 g, 0.113 mmol), N,N-dimethylglycine (0.023 g, 0.226 mmol), and potassium carbonate (0.312 g, 2.26 mmol). Purge with nitrogen 3 times. Add 1-H-pyrazole-4-carboxaldehyde (0.109 g, 1.13 mmol), and DMSO (1.7 mL). Heat to 110° C. for 48 hr. Cool to ambient temperature and partition between ethyl acetate and water. Separate organic layer and extract aqueous layer twice with ethyl acetate. Dry combined organic layers (magnesium sulfate), filter and concentrate. Add copper (I) iodide (0.022 g, 0.113 mmol), N,N-dimethylglycine (0.023 g, 0.226 mmol), potassium carbonate (0.312 g, 2.26 mmol), and DMSO (1.7 mL). Purge with nitrogen 3 times. Heat to 110° C. for 18 hr. Cool to ambient temperature and partition between ethyl acetate and water. Separate organic layer and extract aqueous layer twice with ethyl acetate. Dry combined organic layers (magnesium sulfate), filter, concentrate, and purify (silica gel chromatography, eluting with 50:50 to 100:0 ethyl acetate:hexanes) to give the title preparation (39 mg, 20%). GC-MS: m/z=176 [M+].

1. customIn an oven-dried flask, combine
2. customPurge with nitrogen 3 times
3. temperatureCool to ambient temperature
4. custompartition between ethyl acetate and water
5. extractionSeparate organic layer and extract aqueous layer twice with ethyl acetate
6. customDry
7. filtrationfilter
8. concentrationconcentrate
9. customPurge with nitrogen 3 times
10. temperatureHeat to 110° C. for 18 hr
11. temperatureCool to ambient temperature
12. custompartition between ethyl acetate and water
13. extractionSeparate organic layer and extract aqueous layer twice with ethyl acetate
14. customDry
15. filtrationfilter
16. concentrationconcentrate
17. custompurify
18. wash(silica gel chromatography, eluting with 50:50 to 100:0 ethyl acetate:hexanes)
19. customto give the title
20. custompreparation (39 mg, 20%)