反应详情

Sulfuric acid (1 mL) was added to the product of step 1 (1.4 g, 3.65 mmol) and the resulting mixture stirred at ambient temperature for 2.5 h. Methanol (2 mL) was added and the solution heated at reflux for 3 h. The solution was cooled to room temperature and 1 M NaOH added until a pH=8 was reached. The solution was extracted with ethyl acetate and the combined organics washed with brine, dried (Na2SO4) and concentrated in vacuo. Purification by reverse phase HPLC using a gradient elution of 60:40 H2O/TFA:CH3CN to 0:100 H2O/TFA:CH3CN at 254 nm afforded the title compound as a yellow oil (768 mg, 50%). 1H NMR (CDCl3) δ 7.47 (d, 2H), 7.32-7.25 (m, 3H), 7.14 (m, 2H), 6.61 (d, 2H), 4.38 (t, 1H), 3.70 (s, 3H), 3.25 (brs, 1H), 3.17 (dd, 1H), 3.11 (dd, 1H). MS (ES+) m/z422 (MH+). Anal. Calc. for C19H17NO3F6+0.1H2O: C, 53.93; H, 4.10; N, 3.31. Found: C, 53.73; H, 3.92; N, 3.54.

1. temperaturethe solution heated
2. temperatureat reflux for 3 h
3. temperatureThe solution was cooled to room temperature
4. extractionThe solution was extracted with ethyl acetate
5. washthe combined organics washed with brine
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated in vacuo
8. customPurification by reverse phase HPLC
9. washa gradient elution of 60:40 H2O/TFA