反应详情

温度

120 °C

(4S)-3-[4-(4-Bromophenyl)-1,3-thiazol-2-yl]-4-(fluoromethyl)-1,3-oxazolidin-2-one (0.21 g, 0.59 mmol), prepared in Example 73, and zinc cyanide (41 mg, 0.35 mmol) were dissolved in 8 mL of dimethylformamide. The mixture was purged with nitrogen for 15 min, tetrakis(triphenylphosphine)palladium(0) (34 mg, 0.029 mmol) was added and the mixture was heated to 120° C. for 2 h. The mixture was cooled and diluted with ethyl acetate, and washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. Flash chromatography (100% CH2Cl2) afforded the title compound (146 mg, 81%) as a white solid. mp 195-196° C. HRMS: calcd for C14H10FN3O2S+H+, 304.05505; found (ESI, [M+H]+), 304.0555. Analytical HPLC: retention time 8.8 min, 210-370 nm the Xterra® RP18 column, 3.5%, 150×4.6 mm 40° C. 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min, 1.2 mL/min 5 μL injection.

1. customThe mixture was purged with nitrogen for 15 min
2. temperatureThe mixture was cooled
3. washwashed with water, brine
4. dry with materialdried over anhydrous MgSO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure