Imidazole → HCID 67471170, compound

Participants

Reaction Steps

A 500 mL (one neck) round-bottom flask with a stir bar, septum and needle inlet was charged with (5-bromo-[1,3,4]thiadiazol-2-yl)-methanol (25 g, 128 mmol), DMF (250 mL), imidazole (17.9 g, 263 mmol, 2 equiv.) and TIPSCl (30.0 g, 155 mmol, 1.2 equiv.). The solution was stirred for 5 hours and diluted with EtOAc. The solution was washed with HCl (1N, 2×) and brine. The organic layer was dried over Na2SO4 and concentrated. The crude product was purified by silica gel chromatography (0-10% EtOAc/Hex) to provide 2-bromo-5-triisoproylsilanyloxymethyl-[1,3,4]thiadiazole (44.1 g, 98%).

Provenance & Evidence