Sodium hydride → 4-(5,6-Dichloro-1-benzoimidazol-2-ylmethoxy)-2-fluoro-5-methoxy-benzaldehyde

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2-Fluoro-4-hydroxy-5-methoxy-benzaldehyde (38, 0.364 g, 2.14 mmol) was dissolved in N,N-dimethylformamide (10.0 mL) and sodium hydride (60% dispersion in mineral oil, 100 mg, 2.50 mmol) was added. After 20 minutes, 5,6-dichloro-2-chloromethyl-1H-benzoimidazole (208, 0.420 g, 1.78 mmol) was added. The reaction was stirred at 80° C. overnight. The reaction was concentrated, then washed with ethyl acetate and saturated sodium bicarbonate. The organic portions were dried with anhydrous sodium sulfate, filtered and the filtrate was adsorbed onto silica. The mixture was purified by silica gel chromatography, eluting with methanol/dichloromethane, to provide the desired compound, consistent by 1H-NMR (209, 140 mg, 21%).

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