Water → HCID 178487392, compound

Participants

Reaction Steps

Under an argon atmosphere, a solution of 6-(6-methoxy-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxamidoxime (277 mg) and pyridine (0.121 mL) in tetrahydrofuran (3.1 mL) was ice-cooled. A solution of thionyl chloride (0.055 mL) in methylene chloride (0.62 mL) was added dropwise thereto, and this mixture was stirred at the same temperature for 2 hours. To the reaction mixture was added water, followed by extraction with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: methanol-dichloromethane) to obtain the title compound (60.9 mg). 1H-NMR (DMSO-d6) δ ppm: 3.78 (3H, s), 4.44 (2H, s), 6.64 (1H, dd, J=2.3, 8.5 Hz), 6.89 (1H, d, J=2.3 Hz), 7.18 (1H, dd, J=1.8, 7.3 Hz), 7.26-7.38 (2H, m), 7.41-7.54 (2H, m), 7.59-7.66 (2H, m), 7.79-7.90 (2H, m), 11.23 (1H, s), 11.80-12.20 (1H, br). ESI-MS (m/z): 419 (M+H)+

Provenance & Evidence