Cesium carbonate → N-{4-[5-(2-chloro-5-formylphenyl)-4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-2-furyl]-5-methylpyridin-2-yl}acetamide

Participants

Reaction Steps

To a solution of N-{4-[5-bromo-4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-2-furyl]-5-methylpyridin-2-yl}acetamide (0.45 g, 0.91 mmol) in 1,4-dioxane (5 mL) was added water (1.2 mL), tetrakis(triphenylphosphine)palladium(0) (0.10 g, 0.091 mmol), (2-chloro-5-formylphenyl)boronic acid (0.22 g, 1.19 mmol) and cesium carbonate (0.89 g, 2.74 mmol). The mixture was allowed to stir and subjected to microwave irradiation at 150° C. for 20 min. The mixture was diluted with water and extracted with EtOAc. The organic solution was dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give N-{4-[5-(2-chloro-5-formylphenyl)-4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-2-furyl]-5-methylpyridin-2-yl}acetamide (0.42 g, 83%). LCMS (FA): m/z=552.6 (M+H).

Provenance & Evidence