Hydroxylamine HCl → HCID 86703291, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of hydroxylammonium chloride (373 mg) in dimethylsulfoxide (2.7 mL) was added sodium hydrogen carbonate (541 mg), and this mixture was stirred at 50° C. for 70 minutes. Then, methyl 6-(6-methoxy-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxylate (200 mg) was added thereto, followed by stirring at 50° C. for 3 days. The reaction mixture was left to be cooled and diluted with water, followed by extraction with ethyl acetate. The organic layer was washed with water 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-dichloromethane) to obtain the title compound (186 mg). 1H-NMR (DMSO-d6) δ ppm: 3.77 (3H, s), 4.38 (2H, s), 6.63 (1H, dd, J=2.3, 8.5 Hz), 6.87 (1H, d, J=2.3 Hz), 7.15 (1H, dd, J=1.5, 7.3 Hz), 7.29-7.39 (2H, m), 7.42-7.53 (2H, m), 7.59-7.70 (2H, m), 7.70-7.81 (2H, m), 9.13 (1H, s), 11.10 (1H, s), 11.18 (1H, s). ESI-MS (m/z): 374 (M+H)+

Provenance & Evidence