1,1'-Thiocarbonyldiimidazole → HCID 178487391, compound

Participants

Reaction Steps

Under an argon atmosphere, to a solution of 6-(6-methoxy-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxamidoxime (174 mg) in acetonitrile (3.7 mL) were added 1,1′-thiocarbonyldiimidazole (125 mg) and 1,8-diazabicyclo[5,4,0]-7-undecene (0.278 mL), and this mixture was stirred at room temperature for 22 hours. The reaction mixture was concentrated under reduced pressure. To the residue was added 10% aqueous citric acid solution, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: methanol-ethyl acetate) to obtain the title compound (196 mg). 1H-NMR (DMSO-d6) δ ppm: 3.77 (3H, s), 4.33 (2H, s), 6.63 (1H, dd, J=2.3, 8.7 Hz), 6.88 (1H, d, J=2.3 Hz), 7.12 (1H, dd, J=2.3, 6.5 Hz), 7.28-7.39 (2H, m), 7.41-7.52 (2H, m), 7.68-7.79 (4H, m), 11.16 (1H, s). ESI-MS (m/z): 415 (M+H)+

Provenance & Evidence