反应详情

To a solution of 3-(5-bromo-1H-benzimidazol-1-yl)aniline (1.0 g, 3.5 mmol) in tetrahydrofuran (20 mL) was added p-nitrophenyl chloroformate (980 mg, 4.8 mmol, Aldrich, Cat. 160210), triethylamine (1.4 mL, 10. mmol) and 4-dimethylaminopyridine (80 mg, 0.7 mmol, Aldrich, Cat. 107700). The solution was stirred at r.t. 1 h., then 2,2,2-trifluoroethanamine (520 mg, 5.2 mmol, Alfa Aesar, Cat. No. B20789) was added. The reaction mixture was stirred at r.t. overnight and quenched with NaHCO3 aqueous solution, extracted with ethyl acetate. The combined organic phases were washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatograph on a silica gel column using 85% ethyl acetate in methylene chloride as eluent to afford the desired compound (0.81 g, 56%). LCMS (M+H)+: m/z=413.0.

1. custom1 h.
2. additionB20789) was added
3. stirringThe reaction mixture was stirred at r.t. overnight
4. customquenched with NaHCO3 aqueous solution
5. extractionextracted with ethyl acetate
6. washThe combined organic phases were washed with brine
7. dry with materialdried over MgSO4
8. filtrationAfter filtration
9. concentrationthe filtrate was concentrated under reduced pressure
10. customThe residue was purified by flash chromatograph on a silica gel column