反应详情

A mixture of 0.2885 g bis(triphenylphosphine) palladium dichloride and 0.1565 g copper (I) iodide in 200 mL triethylamine was heated to reflux for 20 min. To the resulting solution was added at room temperature 25.00 g N-(4-iodo-3-pyridinyl)-2,2-dimethyl-propanamide and 25.3 g 5-chloro-1-pentyne and the mixture was heated to reflux for 30 min. The reaction mixture was distributed between water and ethyl acetate, the phases were separated and the organic phase was washed with water and brine, dried over magnesium sulfate and evaporated. The residue was taken up in 200 mL tert-butanol and 18.45 g powdered potassium hydroxyde was added. The mixture was heated to reflux for 30 min. The reaction mixture was distributed between water and ethyl acetate, the phases were separated and the organic phase was washed with water and brine, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on silica gel with ethyl acetate:methanol=7:3 to yield 7.37 g 2,3-Dihydro-1H-3a,5-diaza-cyclopenta[a]indene as slightly yellow solid melting at 90-91° C.

1. temperaturewas heated
2. temperatureto reflux for 20 min
3. temperaturethe mixture was heated
4. temperatureto reflux for 30 min
5. customthe phases were separated
6. washthe organic phase was washed with water and brine
7. dry with materialdried over magnesium sulfate
8. customevaporated
9. additionwas added
10. temperatureThe mixture was heated
11. temperatureto reflux for 30 min
12. customthe phases were separated
13. washthe organic phase was washed with water and brine
14. dry with materialdried over magnesium sulfate
15. customevaporated
16. customThe residue was purified by chromatography on silica gel with ethyl acetate