Dimethylformamide → HCID 25029632, compound

Participants

Reaction Conditions

Reaction Steps

(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.

Provenance & Evidence