Sodium hydride → 2-[1-(3,5-dichlorobenzyl)-1H-imidazol-2-ylmethoxy]-6-fluoro-pyridine

Participants

Reaction Steps

[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-yl]-methanol (300 mg, 1.17 mmol) was dissolved in DMF and NaH (46 mg, 1.17 mmol) was added under N2 atmosphere. After 20 minutes, 2,6-di-fluoropyridine (0.11 mL, 1.17 mmol) was added. The reaction mixture was stirred at room temperature for 1 h. The reaction was partitioned between EtOAc (50 mL) and water (50 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×75 mL). The combined organic extracts were washed with water (2×70 mL) and brine, dried over MgSO4, filtered and concentrated to yield a yellow solid. Chromatography (silica, 40:1 CH2Cl2/MeOH) afforded 2-[1-(3,5-dichlorobenzyl)-1H-imidazol-2-ylmethoxy]-6-fluoro-pyridine (270 mg, 66%).

Provenance & Evidence