Sodium hydride → 4-[2-(4,4-Dimethyl-2-oxo-1,3-oxazolidin-3-yl)-1,3-oxazol-4-yl]benzonitrile

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Reaction Conditions

Reaction Steps

A 5 mL flask was charged with 4,4-dimethyl-oxazolidin-2-one (1.0 g, 8.7 mmol) and sodium hydride (60% wt suspension in mineral oil) (40 mg, 1.2 mmol) was added and the mixture was stirred for 20 min. 4-(2-Iodo-1,3-oxazol-4-yl)benzonitrile (0.257 g, 0.87 mmol), prepared in the previous step, was added and the mixture was heated to 170° C. for 2 h then cooled and diluted with ethyl acetate. The organics were combined, washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated. Flash chromatography (15% acetone in hexane) afforded the title compound (9 mg, 4%). HRMS: calcd for C15H13N3O3+H+, 284.10297; found (ESI, [M+H]+), 284.1024; Analytical HPLC: purity 95.3% at 210-370 nm, 8.1 min; 98.3% at 278 nm, 8.1 min; the Xterra® RP18 column, 3.5%, 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