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With cesium fluoride;bis(tri-tert-butylphosphine)palladium(0); In 1,4-dioxane; at 100℃; for 16h;
To a mixture of <strong>[850568-54-6]4-(tert-butoxycarbonyl)phenylboronic acid</strong> (4.05 g, 17.1 mmol), cesium fluoride (5.57 g, 36.7 mmol), and Pd[P(t-Bu)3]2 (0.708 g, 1.39 mmol) was added dioxane (65 mL) and 3-bromo-5-chloro-l,2,4-thiadiazole (5.02 g, 25.2 mmol). The reaction mixture was degassed by bubbling nitrogen through the solution for 10 minutes and the solution was heated to 100°C. After 16 h, the reaction mixture was partially concentrated and diluted with EtOAc. The organic phase was washed with water (1 x), brine (1 x), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 5percent to 10percent EtOAc in hexanes) gave tert-butyl 4-(3-bromo-l,2,4-thiadiazol-5- yl)phenylcarbamate.