Sodium hydride → 2,4-dibromo-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)thiazole

Participants

Reaction Steps

To a mixture of sodium hydride (2.89 g, 72.2 mmol) in THF (431 mL) was added 2,4-dibromo-5-(1H-imidazol-2-yl)thiazole (18.81 g, 60.88 mmol) in THF (60 mL) at 0° C. After stirring 30 min, [β-(Trimethylsilyl)ethoxy]methyl chloride (11.85 mL, 66.96 mmol) in THF (24 mL) was slowly added at 0° C. After 30 min at this temperature, the reaction was quenched by addition of MeOH (20 mL). The solvent was evaporated and the residue was purified by ISCO chromatography, eluted with EtOAc in hexanes, 0-25%. Product was obtained as colorless oil (21.84 g, 81.6%). LCMS: (AA) ES+, 440, 442. 1H NMR (300 MHz, d1-chloroform) δ: 7.24 (dd, 2H) 5.27 (s, 2H) 3.39 (t, 2H) 0.85 (t, 2H) −0.03 (s, 9H).

Provenance & Evidence