Cesium carbonate → 1-[4-(4-{2-[2-(4-pentafluorosulfanyl-phenyl)-vinyl]-oxazol-4-ylmethanesulfonyl}-phenyl)-butyl]-1H-[1,2,3]triazole

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Reaction Steps

A solution of 1-but-3-enyl-1H-[1,2,3]triazole (80 mg, 0.65 mmol) in anhydrous THF (5 ml) was treated with 9-BBN (0.5 M in THF, 2.86 ml, 1.43 mmol) at 0° C. and stirred for 2 h at room temperature. This mixture was added to a solution of 4-(4-bromo-benzenesulfonylmethyl)-2-[2-(4-pentafluorosulfanyl-phenyl)-vinyl]-oxazole (345 mg, 0.65 mmol), [Pd(dppf)Cl2] (57 mg, 0.07 mmol) and aqueous cesium carbonate (3M, 0.65 ml, 1.95 mmol) in N,N-dimethyl formamide (4 ml) and stirred for 3 h at 70° C. After cooling to room temperature ethyl acetate (100 ml) was added and the solution washed with water (2×50 ml). The organic layer was concentrated and the crude product purified by flash column chromatography (ethyl acetate) and crystallization from diethyl ether to yield 1-[4-(4-{2-[2-(4-pentafluorosulfanyl-phenyl)-vinyl]-oxazol-4-ylmethanesulfonyl}-phenyl)-butyl]-1H-[1,2,3]triazole as white solid (213 mg, 57%).

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