Cesium carbonate → 6-(2,4-Difluorophenyl)-5-(2-(methylthio)pyrimidin-5-yl)imidazo[2,1-b]oxazole

Participants

Reaction Conditions

Reaction Steps

A round bottom flask was charged with 6-(2,4-difluorophenyl)-5-iodoimidazo[2,1-b]oxazole (0.25 g, 0.72 mmol; Example #8, step C) and 2-(methylthio)pyrimidin-5-ylboronic acid (0.184 g, 1.08 mmol, Indofine), bis(triphenylphosphine)palladium (II) chloride (0.051 g, 0.072 mmol) and cesium carbonate (0.588 g, 1.81 mmol). The reaction mixture was diluted with 1,4-dioxane (10 mL) and water (2 mL). The reaction mixture was degassed under vacuum and purged with nitrogen 3 times and then stirred at about 90° C. for about 4 h. The reaction mixture was cooled to ambient temperature and then diluted with H2O. The mixture was extracted with EtOAc (2×200 mL). The organic layers were combined and concentrated under reduced pressure. The product was purified by silica gel flash chromatography using a gradient of 0-10% EtOAc in DCM to give the title compound as yellow solid (0.17 g, 64%); 1H NMR (DMSO-d6) δ 8.62 (s, 2H), 8.34 (d, J=1.8, 1H), 8.12 (d, J=1.8, 1H), 7.68 (m, 1H), 7.33-7.25 (m, 1H), 7.20 (m, 1H), 2.54 (s, 3H).

Provenance & Evidence