Cesium carbonate → HCID 25096955, compound

Participants

Reaction Steps

A solution of N-[(2-chloro-4-fluorophenyl)methyl]-3-methyl-2-oxo-4-imidazolidinecarboxamide (28.6 mg, 0.1 mmol) (prepared as described in Example 29) and 3-bromopyridine (15.8 mg, 0.1 mmol) in 1,4-dioxane (3 ml) was treated with cesium carbonate (81 mg, 0.25 mmol), Xantphos™ (4.3 mg, 0.075 mmol) and tris(dibenzylideneacetone)dipalladium(0) (2.3 mg, 0.025 mmol) and the mixture was heated under reflux under argon for 18 hours. 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 0-10% methanol in dichloromethane. The resulting residue was triturated with ether, the solid collected and dried to give N-[(2-chloro-4-fluorophenyl)methyl]-3-methyl-2-oxo-1-(3-pyridinyl)-4-imidazolidinecarboxamide (18 mg, 50%). LC/MS [M+H]+=363, retention time 1.68 minutes.

Provenance & Evidence