Dimethylformamide → 4-[5-(4,4-Dimethyl-2-oxo-1,3-oxazolidin-3-yl)-1,2,4-thiadiazol-3-yl]benzonitrile

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Reaction Conditions

Reaction Steps

3-[3-(4-bromophenyl)-1,2,4-thiadiazol-5-yl]-4,4-dimethyl-1,3-oxazolidin-2-one (0.67 g, 1.9 mmol), prepared in step 4 of Example 93, was dissolved in dimethylformamide (19 mL). Zinc cyanide (0.132 g, 1.14 mmol) was added, the mixture was purged with nitrogen for 15 min, and then tetrakis(triphenylphosphine)palladium (0.11 g, 0.095 mmol) was added. The mixture was heated to 120° C. for 2 h, additional tetrakis(triphenylphosphine)palladium (0.11 g, 0.095 mmol) was added and stirring was continued for 45 min. The mixture was cooled, diluted with ethyl acetate, washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated. Flash chromatography (10% acetone in hexane) afforded the title compound (0.48 g, 84%) as a white solid. Analytical HPLC: HPLC purity 100% at 210-370 nm, 9.7 min; 100% at 248 nm, 9.7 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

Provenance & Evidence