Cesium carbonate → HCID 86640215, compound

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl 3-methyl-2-oxo-4-imidazolidinecarboxylate (650 mg, 3.25 mmol) (prepared as described in step (iii) of Example 13, starting from (4S)-2-oxo-3-{[(phenylmethyl)oxy]carbonyl}-4-imidazolidinecarboxylic acid) and 3-bromo-2-chloropyridine (625 mg, 3.25 mmol) in 1,4-dioxane (30 ml) was added cesium carbonate (4231 mg, 12.98 mmol), tris(dibenzylideneacetone)dipalladium(0) (149 mg, 0.162 mmol) and Xantphos™ (141 mg, 0.243 mmol) and the reaction stirred at reflux overnight. The reaction mixture was allowed to cool and solvent was removed under vacuum and the residue partitioned between ethyl acetate and water. The organic layer was separated and washed with saturated sodium hydrogen carbonate solution, water and brine and separated by hydrophobic frit. The organic solution was reduced under vacuum and the residue purified by SP4 automated silica gel chromatography eluting with 10-80% ethyl acetate in iso-hexane to give 1,1-dimethylethyl 1-(2-chloro-3-pyridinyl)-3-methyl-2-oxo-4-imidazolidinecarboxylate (579 mg, 51.5% yield)

Provenance & Evidence