反应详情

温度

0 °C

To a mixture of 7 (65 mg, 0.200 mmol), 4-(2-(dimethylamino)ethoxy)benzenamine dihydrochloride (42.6 mg, 0.168 mmol), 4-Dimethylaminopyridine (1.2 mg, 0.00982 mmol) in CH2Cl2 (3 ml) was added O-Benzotriazoyl-N,N,N′,N′-tetramethyluronium Hexafluorophosphate (83.4 mg, 0.220 mmol) under ice cooling, and the mixture was stirred at 0° C. for 10 min. Then N,N-Diisopropylethylamine (90.4 mg, 0.701 mmol) was added under ice cooling. The mixture was stirred at 0° C. for 5 min, and at room temperature for 15 h. The reaction was quenched with saturated aqueous NaHCO3 under ice cooling, and the whole was extracted with CHCl3, the organic layer was washed with brine, dried over Na2SO4, and then concentrated. Purification by silica gel flash column chromatography (eluent: CH2Cl2 to CH2Cl2/MeOH, 6:1) gave the colorless solid (100%). The solid was triturated with hexane to give 8 (80%). 8: colorless powder; 1H-NMR (CDCl3) δ 0.45 (2H, m), 0.79 (2H, m), 2.36 (6H, s), 2.55 (1H, m), 2.76 (2H, t, J=5.5 Hz), 3.41 (3H, s), 4.07 (2H, t, J=5.5 Hz), 5.05 (2H, s), 6.74 (2H, d, J=8.8 Hz), 6.88 (2H, d, J=8.8 Hz), 6.95-6.99 (4H, m), 7.10-7.20 (4H, m), 7.44 (2H, d, J=8.8 Hz).

1. stirringThe mixture was stirred at 0° C. for 5 min
2. waitat room temperature for 15 h
3. customThe reaction was quenched with saturated aqueous NaHCO3 under ice cooling
4. extractionthe whole was extracted with CHCl3
5. washthe organic layer was washed with brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated
8. customPurification by silica gel flash column chromatography (eluent: CH2Cl2 to CH2Cl2/MeOH, 6:1)