反应详情

温度

80 °C

5-Bromo-2-chloro-N-cyclopropyl-benzamide (19.3 g, 70.5 mmol) was dissolved in a mixture of DMF (350 mL) and 1-propanol (210 mL). Pd(OAc)2(PPh3)3 (2.64 g, 3.53 mmol) was added. (E)-2-(3-Methoxypropenyl)4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15 mL, 70.5 mmol) was added through a syringe, and aq. 2M Na2CO3 (123 mL) was added. The mixture was stirred at 80° C. for 2 h, and allowed to cool to rt. Aq. 10% HCl was added carefully until a pH of 2 was reached. The solvents were partially removed under reduced pressure, and the residue was extracted with Et2O (3×). The combined org. extracts were washed with water and brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 1:2→1:1→EtOAc) yielded the title compound (12.7 g, 68%). LC-MS: tR=0.82 min; ES+: 266.17.

1. temperatureto cool to rt
2. customThe solvents were partially removed under reduced pressure
3. extractionthe residue was extracted with Et2O (3×)
4. washextracts were washed with water and brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customthe solvents were removed under reduced pressure
8. customPurification of the residue by FC (EtOAc/heptane 1:2→1:1→EtOAc)