反应详情

温度

55 °C

1,2-Dichloroethane (1.02 mL) was added to a mixture of 8-[1,4]diazepan-1-yl-7-methoxy-quinoline (1.00 g, 3.88 mmol) and 2-(4-hydroxy-piperidin-1-yl)-thiazole-4-carbaldehyde (824 mg, 3.88 mmol). The reaction was heated to 55° C. and stirred until homogeneous. Freshly crushed Ti(OMe)4 (1.00 g, 5.82 mmol) was then added and the reaction was stirred at 55° C. for 1 h. tert-Butyl-(1-methoxy-vinyloxy)-dimethyl-silane (1.02 mL, 4.66 mmol) was then added and the reaction was stirred at 55° C. for 18 h. CH2Cl2 was then added, followed by sat. aq. NaHCO3, then 1 N aq. NaOH. This mixture was then stirred for 5 min and filtered through celite, washing the filter cake with CH2Cl2. The filtrate was then washed once with H2O, dried over MgSO4, filtered, and concentrated. The crude product was purified on silica gel (99:1 to 90:10 CH2Cl2:(9:1 MeOH:NH4OH)) to give the product (660 mg, 38% yield).

1. additionwas then added
2. stirringthe reaction was stirred at 55° C. for 18 h
3. stirringThis mixture was then stirred for 5 min
4. filtrationfiltered through celite
5. washwashing the filter cake with CH2Cl2
6. washThe filtrate was then washed once with H2O
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude product was purified on silica gel (99:1 to 90:10 CH2Cl2:(9:1 MeOH:NH4OH))