Cesium carbonate → 1-(2-cyano-3-pyridinyl)-N-[(2,4-dichlorophenyl)methyl]-3-methyl-2-oxo-4-imidazolidinecarboxamide

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Reaction Steps

A suspension of N-[(2,4-dichlorophenyl)methyl]-3-methyl-2-oxo-4-imidazolidinecarboxamide (200 mg, 0.662 mmol) (prepared as described in Example 30) and 3-bromo-2-pyridinecarbonitrile (121 mg, 0.662 mmol) in 1,4-dioxane (5 ml) was treated with cesium carbonate (323 mg, 0.993 mmol), Xantphos™ (28.7 mg, 0.050 mmol) and tris(dibenzylideneacetone)dipalladium(0) (15.15 mg, 0.017 mmol) and the mixture was heated at reflux under argon for overnight. After cooling to room temperature, the reaction mixture was diluted with saturated sodium hydrogen carbonate solution and extracted with dichloromethane. The organic layers were combined, washed with water and brine and evaporated in vacuo. The residue was purified by silica gel chromatography eluting with 10-100% ethyl acetate in isohexane to give 1-(2-cyano-3-pyridinyl)-N-[(2,4-dichlorophenyl)methyl]-3-methyl-2-oxo-4-imidazolidinecarboxamide (212 mg, 78% yield). LC/MS [M+H]+=404, retention time=2.32 minutes.

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