Water → Racemic 4-{2-[2-oxo-4-(trifluoromethyl)-1,3-oxazolidin-3-yl]-1,3-thiazol-4-yl}benzonitrile

Participants

Reaction Conditions

Reaction Steps

3-[4-(4-Bromophenyl)-1,3-thiazol-2-yl]-4-(trifluoromethyl)-1,3-oxazolidin-2-one, prepared in step 3 of Example 64, (0.455 g, 1.15 mmol) and zinc cyanide (81 mg, 0.69 mmol) were dissolved in 12 mL of DMF. The mixture was purged with nitrogen for 15 min and then tetrakis(triphenylphosphine)palladium(0) (66.5 mg, 0.058 mmol) was added and the mixture was heated to 120° C. for 1.5 h. The mixture was cooled and diluted with ethyl acetate and poured into 200 mL of water. The mixture was extracted with ethyl acetate, the organics were combined, washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. Flash chromatography (gradient 1% acetone/hexane to 10% acetone/hexane) afforded racemic 4-{2-[2-oxo-4-(trifluoromethyl)-1,3-oxazolidin-3-yl]-1,3-thiazol-4-yl}benzonitrile (278 mg, 72%) as a white solid.

Provenance & Evidence