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

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Reaction Conditions

Reaction Steps

3-[4-(4-Bromophenyl)-1,3-thiazol-2-yl]-4-(2,2,2-trifluoroethyl)-1,3-oxazolidin-2-one (0.53 g, 1.3 mmol), prepared in step 3 of Example 67, and zinc cyanide (91 mg, 0.78 mmol) were dissolved in 15 mL of DMF. The mixture was purged with nitrogen for 15 min, tetrakis(triphenylphosphine)palladium(0) (75 mg, 0.065 mmol) was added, and the mixture was heated at 120° C. for 3 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 (25% hexane in methylene chloride) afforded racemic 4-{2-[2-oxo-4-(2,2,2-trifluoroethyl)-1,3-oxazolidin-3-yl]-1,3-thiazol-4-yl}benzonitrile (364 mg, 79%) as a white solid.

Provenance & Evidence