4-Chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl trifluoromethanesulfonate (1.1 g, 3.1 mmol) was dissolved in a mixture of 1,4-dioxane and water (15 mL:3.0 mL) and treated with [4-(hydroxymethyl)phenyl]boronic acid (0.70 g, 4.6 mmol), potassium phosphate (2.0 g, 9.2 mmol) and palladium(0) tetrakis(triphenylphosphine) (0.18 g, 0.15 mmol). The mixture was placed into a preheated oil bath at 90° C. for 1 hour. The mixture was cooled to ambient temperature, poured into sodium bicarbonate (150 mL, aqueous saturated) and extracted with ethyl acetate (2×250 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (100:0 to 0:100; hexane:ethyl acetate) to afford the titled compound.
