Nitrogen → 5-Bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d][1,2,3]triazole

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Reaction Steps

A 250-mL round-bottom flask equipped with a magnetic stir bar, a rubber septum and N2 inlet was charged with 5-bromo-1H-benzo[d][1,2,3]triazole (4.5 g, 22.7 mmol) and anhydrous dichloromethane (114 mL). To this solution, 3,4-dihydro-2H-pyran (10.3 mL, 113.6 mmol) was added in one portion at room temperature followed by addition of PPTS (0.57 g, 2.27 mmol). The resulting mixture was stirred at room temperature for 48 h. The reaction was monitored by TLC. Upon completion, the reaction mixture was quenched with water and extracted with dichloromethane (3×100 mL). The combined organic layers were washed with saturated NaHCO3 (50 mL), water (100 mL), and then brine (50 mL), dried over sodium sulfate, filtered and concentrated to give the crude product that was purified on a silica gel column eluted with 0-10% ethyl acetate in hexanes affording the title compound as a clear oil (3.6 g). LCMS: 198 [(M-THP+H)+H]+.

Provenance & Evidence