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

Participants

Reaction Steps

A solution of 1-but-3-enyl-1H-[1,2,3]triazole (0.14 g, 1.14 mmol) in anhydrous THF (10 ml) was treated with 9-BBN (0.5 M in THF, 5 ml, 2.5 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-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazole (0.6 g, 1.15 mmol), [Pd(dppf)Cl2] (98 mg, 0.12 mmol) and aqueous cesium carbonate (3M, 1.15 ml, 3.45 mmol) in N,N-dimethyl formamide (7 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-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethanesulfonyl}-phenyl)-butyl]-1H-[1,2,3]triazole as white solid (0.36 g, 55%).

Provenance & Evidence