Sodium hydride → 3-(4-Bromophenyl)-1-methyl-4-[[2-(trimethylsilyl)ethoxy]methyl]-4,5-dihydro-1H-1,2,4-triazol-5-one

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Reaction Steps

To a solution of compound 10b (1.00 g, 3.94 mmol) in DMF (5 mL) was added sodium hydride (200 mg, 5.00 mmol) in portions at 0° C., and the mixture was stirred for 20 min before 2-(trimethylsilyl)ethoxymethyl chloride (730 mg, 4.37 mmol) was added. The reaction mixture was stirred at rt overnight, and was quenched with H2O (50 mL). The resulting mixture was extracted with DCM (2×50 mL). The combined organic layers were dried over Na2SO4, filtered concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc/petroleum ether (1:5 v/v) to obtain compound 10c as a yellow solid (600 mg, 40% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C15H22BrN3O2Si: 383.1 (M+H). Found 383.1.

Provenance & Evidence