反应详情

温度

-78 °C

To a mixture of a-Methyl-4-[4-(4-fluorophenyl)-5-(4-pyridyl)-imidazol-2-yl]benzyl alcohol (0.25 g, 0.70 mmol), P(Ph)3 (0.46 g, 1.75 mmol) and N,O-bis(benzyloxycarbonyl)hydroxylamine (0.48 g, 1.75 mmol) in THF (15 mL) was added DEAD (0.28 mL, 1.75 mmol) at rt. The reaction mixture was stirred at this temperature for 3 h and the solvent evaporated. The residue was partially purified by flash chromatography eluting with 1% MeOH/CHCl3. Methanol (25 mL) was added to this material and the mixture was cooled to −78° C. Ammonia was bubbled in at this temperature for 15 min. The reaction mixture was warmed slowly to rt, stoppered and stirred at rt for 2 days. The solvent was evaporated and the residue was purified by flash chromatography eluting with a solvent gradient of 1-10% MeOH/CHCl3. The title compound was obtained as an off-white solid (0.43 g, 14%): FABMS (m/z): 418 (M++H).

1. customthe solvent evaporated
2. customThe residue was partially purified by flash chromatography
3. washeluting with 1% MeOH/CHCl3
4. additionMethanol (25 mL) was added to this material
5. customAmmonia was bubbled in at this temperature for 15 min
6. temperatureThe reaction mixture was warmed slowly to rt
7. stirringstirred at rt for 2 days
8. customThe solvent was evaporated
9. customthe residue was purified by flash chromatography
10. washeluting with a solvent gradient of 1-10% MeOH/CHCl3