反应详情

温度

50 °C

NaH (13.2 mg, 60% in mineral oil, 0.330 mmol) was added to a 0° C. solution of N-(4-(4-(4-hydroxypiperidin-1-yl)-2,6-dimethylphenyl)thiazol-2-yl)isonicotinamide (14.8 mg, 0.0362 mmol) in dry DMF (0.5 mL); the mixture was then stirred at 50° C. for 20 min. After that, the mixture was cooled to 0° C., and a solution of 1-azido-2-(2-(2-(2-iodoethoxyl)ethoxy)ethoxy)ethane (14.3 mg, 0.0435 mmol)6 in DMF (0.15 mL) was added dropwise. The mixture was stirred at rt overnight. Water (2 mL) was added to quench the reaction, and the mixture was extracted with DCM (4×2 mL). The combined organic layer was washed with brine and concentrated. The residue was briefly purified on a short silica column (EtOAc) to furnish N-(4-(4-(4-(2-(2-(2-(2-azidoethoxyl)ethoxy)ethoxy)ethoxy)piperidin-1-yl)-2,6-dimethylphenyl)thiazol-2-yl)isonicotinamide (4.7 mg, 21.3%). MS (ESI) m/z 632.4 (M+Na+).

1. temperatureAfter that, the mixture was cooled to 0° C.
2. stirringThe mixture was stirred at rt overnight
3. customto quench
4. customthe reaction
5. extractionthe mixture was extracted with DCM (4×2 mL)
6. washThe combined organic layer was washed with brine
7. concentrationconcentrated
8. customThe residue was briefly purified on a short silica column (EtOAc)