Diphenyl sulfide → HCID 178510919, compound

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Reaction Steps

A solution of 4-chloro-N-{[4-chloro-3-({3-chloro-5-[(E)-2-cyanoethenyl]phenyl}oxy)-2-fluorophenyl]methyl}-1H-imidazole-5-carboxamide (32 mg, 0.069 mmol), diphenylsulfide (1.145 μl, 6.87 μmol) and Pd/C (7.31 mg, 6.87 μmol) in methanol (5 ml) and ethyl acetate (5 ml) was stirred under hydrogen gas (45 psi pressure) overnight. The palladium was filtered off, the solvent was removed and the crude material was purified via silica gel chromatography to give 4-chloro-N-[(4-chloro-3-{[3-chloro-5-(2-cyanoethyl)phenyl]oxy}-2-fluorophenyl)methyl]-1H-imidazole-5-carboxamide (22 mg, 0.047 mmol, 69% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.69 (s, 1H), 7.15-7.40 (m, 2H), 7.04 (s, 1H), 6.77 (s, 1H), 6.73 (s, 1H), 4.61 (s, 2H), 2.87 (t, 2H), 2.69 (t, 2H). LC-MS (ES+) m/z 467.02, [M+H].

Provenance & Evidence