Sodium periodate → 4-chloro-N-({4-chloro-3-[(3-chloro-5-formylphenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide

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Reaction Steps

To a solution of 4-chloro-N-({4-chloro-3-[(3-chloro-5-ethenylphenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (240 mg, 0.420 mmol) and sodium periodate (270 mg, 1.261 mmol) in dioxane (5 mL) and water (3 ml) was added osmium tetroxide (2.5% solution in t-butanol) (0.106 ml, 8.44 μmol) and the mixture was stirred at room temperature for 5 hours. The mixture was diluted with EtOAc, washed with water and the solvent was removed. The crude material was purified via silica gel chromatography to give 4-chloro-N-({4-chloro-3-[(3-chloro-5-formylphenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (189 mg, 0.330 mmol, 78% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.92 (s, 1H), 8.79 (t, 1H), 8.00 (s, 1H), 7.65-7.82 (m, 1H), 7.48-7.57 (m, 1H), 7.37-7.49 (m, 2H), 7.28 (d, 1H), 5.51 (s, 2H), 4.51 (d, 2H), 3.21-3.60 (m, 2H), 0.77 (t, 2H), −0.07 (s, 9H)

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