Sodium hydride → Methyl 4-{[(4-tert-butylcyclohexyl)(1-{2-[(trimethylsilyl)oxy]ethyl}-1H-benz-imidazol-2-yl)amino]methyl}benzoate

Participants

Reaction Conditions

Reaction Steps

To the title compound from Example 1 Step C (0.5 mmol, 210 mg) in 1 mL of THF was added a solution of NaH (1 mmol, 40 mg of 60% slurry in mineral oil) in 1 mL of DMF (exothermic, H2 evolution). After gas evolution ceased for several minutes, (2-bromoethoxy)(trimethyl)silane was added to the solution via syringe. The reaction mixture was heated to 40° C. After 2.5 h the reaction was quenched by addition of saturated ammonium chloride. The product was extracted 3× with EtOAc and the organic phase was dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica eluting with 5% EtOAc/hexanes. HPLC A: 3.14 min.

Provenance & Evidence