反应详情

温度

120 °C

3-Amino-5-bromobenzotrifluoride (6 g, 25 mmol) and 1-(1H-imidazol-2-yl)-N,N-dimethylmethanamine (3.7 g, 29.6 mmol) were dissolved in anhydrous DMSO (25 mL). To this was added CuI (0.95 g, 7.5 mmol), 8-hydroxy quinoline (0.72 g, 7.5 mmol) and K2CO3 (6.9 g, 50 mmol). The mixture was stirred vigorously and degassed with N2 for 15 minutes. The flask was then equipped with a condenser and heated at 120° C. for 18 h. The resultant heterogeneous mixture was cooled to rt, poured into 14% aq. NH4OH (100 mL) and extracted with EtOAc (3×300 ml). The combined extracts were dried over NaSO4 and concentrated in vacuo. The residue was chromatographed over silica gel eluting with MeOH/DCM (5:95) to furnish 3.5 g of the desired product as a tan colored material: 285 m/z (M+H).

1. customdegassed with N2 for 15 minutes
2. customThe flask was then equipped with a condenser
3. temperatureThe resultant heterogeneous mixture was cooled to rt
4. additionpoured into 14% aq. NH4OH (100 mL)
5. extractionextracted with EtOAc (3×300 ml)
6. dry with materialThe combined extracts were dried over NaSO4
7. concentrationconcentrated in vacuo
8. customThe residue was chromatographed over silica gel eluting with MeOH/DCM (5:95)