Diphenyl sulfide → HCID 178436596, compound

Participants

Reaction Steps

A solution of 4-chloro-N-({4-chloro-3-[(4-cyano-6-ethenyl-2-pyridinyl)oxy]-2-fluorophenyl}methyl)-2-methyl-1H-imidazole-5-carboxamide (53 mg, 0.119 mmol), diphenylsulfide (1.979 μl, 0.012 mmol) and palladium on carbon (12.64 mg, 0.012 mmol, 10%) in MeOH (8.0 ml) and ethyl acetate (8.00 ml) was reacted under H2 (40 psi) overnight. The reaction mixture was filtered through a pad of celite and concentrated to dryness. The residue was purified by flash chromatography on silica gel eluted with 0-5% 2M NH3 solution of MeOH in CH2Cl2 to give the title compound as a white solid (43 mg, 81%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 10.82 (1H, br. s.) 7.17-7.24 (2H, m) 7.09 (2H, d, J=5.4 Hz) 4.68 (2H, d, J=6.0 Hz) 2.61 (2H, q, J=7.5 Hz) 2.39 (3H, s) 1.07 (3H, t). LCMS: m/z 448 (M+1).

Provenance & Evidence