Acetone → HCID 58754814, compound

Participants

Reaction Steps

To a solution of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (4-bromo-2-cyclohex-1-enyl-phenyl)-amide (as prepared in Example 11, step (f), 50.0 mg, 0.100 mmol) in 1 mL of THF at −78° C. under Ar was added isopropyl magnesium chloride (55 μL, 0.11 mmol, 2.0 M in THF). The resulting mixture was warmed to RT and stirred for 15 min, cooled back to −78° C. To the mixture was added n-butyllithium (55 μL, 0.11 mmol, 2.0 M in cyclohexane) and the resulting mixture was stirred at −78° C. for 0.5 h under Ar. Acetone (30 μL, 0.40 mmol) was added and the reaction was warmed to RT and stirred for 16 h under Ar. Treated with 5 mL of saturated NH4Cl aqueous solution followed by 30 mL of EtOAc, the mixture was washed with H2O (10 mL), brine (5 mL) and dried (Na2SO4). The solvent was evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel (5-10% EtOAc/hexane) to afford 40.0 mg (84%) of the title compound as a white solid. Mass spectrum (ESI, m/z): Calcd. for C26H35BrN4O3Si, 559.2 (M+H), found 558.9.

Provenance & Evidence