2-Methyl-2-butene → HCID 68725206, compound

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To a solution of 4-chloro-N-({4-chloro-3-[(3-cyano-5-formylphenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (200 mg, 0.355 mmol) in 2-methyl-2-butene (4.44 ml, 4.44 mmol) was added a solution of sodium chlorite (401 mg, 3.55 mmol) and sodium dihydrogenphosphate monohydride (302 mg, 2.130 mmol) in water (2 mL). The mixture was stirred for 4 hours and the solvent was removed under vacuum. The residue was diluted with EtOAc and washed with water. The organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by reverse phase HPLC (MeCN/water 0.1% formic acid) to give 130 mg (63%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.78 (t, 1H), 7.88-8.14 (m, 2H), 7.81 (s, 1H), 7.31-7.61 (m, 3H), 5.49 (s, 2H), 4.35-4.59 (m, 2 H), 3.31 (s, 2H), 0.57-0.85 (m, 2H), −0.09 (s, 9H). LC-MS (ES+) m/z 578.25, [M+H].

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