反应详情

温度

65 °C

To 268 mg (0.62 mmol) of 7-6 in CH2Cl2 was added 175 μL (1.24 mmol) of triethylamine and 75 mL (0.93 mmol) of mesyl chloride. After stirring for 1 h, the mixture was dumped into a separatory funnel with saturated NaHCO3, extracted twice with CH2Cl2, washed with water, and dried over Na2SO4. The residue was dissolved in DMF, 82 mg (1.24 mmol) of sodium azide was added, and the reaction was heated for 4 h at 65° C. After cooling to rt, the mixture was dumped into brine, extracted twice with EtOAc, and then washed with brine. The organic layer was dried over Na2SO4, concentrated, redissolved in THF and 205 mg (0.78 mmol) of triphenylphosphine was added. After stirring for 15 h, 1 mL of water was added and the mixture was heated at 65° C. for 1 h. The reaction was worked up with EtOAc and brine, dried over Na2SO4, concentrated, and purified by column chromatography on silica gel with CH2Cl2/MeOH/TEA to provide 7-7 as a white solid. Data for 7-7: 1HNMR (500 MHz, CDCl3) δ 7.5 (m, 1H), 7.4-7.2 (m, 5H), 7.1-7.0 (m, 2H), 3.8-3.6 (m, 4H), 3.6 (m, 4H), 3.5 (m, 1H), 3.4 (m, 1H), 2.9-2.8 (m, 3H), 2.2 (m, 1H), 1.6 (m, 2H) ppm. HRMS (ES) calc'd M+Na for C23H26F2N4O2: 429.2097. Found: 429.2097.

1. extractionextracted twice with CH2Cl2
2. washwashed with water
3. dry with materialdried over Na2SO4
4. dissolutionThe residue was dissolved in DMF
5. temperatureAfter cooling to rt
6. extractionextracted twice with EtOAc
7. washwashed with brine
8. dry with materialThe organic layer was dried over Na2SO4
9. concentrationconcentrated
10. dissolutionredissolved in THF
11. stirringAfter stirring for 15 h
12. temperaturethe mixture was heated at 65° C. for 1 h
13. dry with materialdried over Na2SO4
14. concentrationconcentrated
15. custompurified by column chromatography on silica gel with CH2Cl2/MeOH/TEA