Water → HCID 66727697, compound

Participants

Reaction Steps

To a stirred mixture of 5-bromopyridin-2-ol (500 mg) in DMF (10 mL) was added NaH (60% in oil, 115 mg) at room temperature. The mixture was stirred at room temperature for 30 min and then 2-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzo[d]imidazole (813 mg) was added. The mixture was exposed to microwave irradiation at 200° C. for 1 h, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/MeOH) and crystallized from AcOEt/hexane to give 2-(5-bromopyridin-2-yloxy)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole (336 mg) and 5-bromo-1-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzo[d]imidazol-2-yl)pyridin-2(1H)-one (170 mg).

Provenance & Evidence