反应详情

温度

0 °C

Sodium hydride (119 mg, 2.97 mmol) was added to a stirred solution of tert-butyl 4-(2-hydroxypropyl)pyridin-2-ylcarbamate (47) (250 mg, 0.991 mmol) in DMF (6 mL) at 0° C., under nitrogen and after 45 min a solution of 1-fluoro-4-nitronaphthalene (14) (189 mg, 0.991 mmol) in DMF (6 mL) was added dropwise, over 2 min. The resulting dark-brown reaction mixture was stirred at 0° C. for 5 min, and was then warmed to RT. After 70 min, a saturated aqueous solution of NH4Cl (3 mL) was added and the mixture was partitioned between water and EtOAc. The aqueous layer was extracted twice with EtOAc and the combined organic extracts were washed with brine, dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 40 g; 0-70% EtOAc in isohexane, gradient elution) to afford the title compound (48) (293 mg, 65%) as an orange foam: m/z 424.0 (M+H)+ (ES+).

1. additionwas added dropwise, over 2 min
2. temperaturewas then warmed to RT
3. waitAfter 70 min
4. customthe mixture was partitioned between water and EtOAc
5. extractionThe aqueous layer was extracted twice with EtOAc
6. washthe combined organic extracts were washed with brine
7. dry with materialdried (MgSO4)
8. customevaporated in vacuo
9. customThe residue was purified by flash column chromatography (SiO2, 40 g; 0-70% EtOAc in isohexane, gradient elution)