Hydrochloric Acid → HCID 178487389, compound

Participants

Reaction Steps

To a solution of methyl [6-(6-methoxy-2-phenyl-1H-indol-3-ylmethyl)pyridin-2-yl]propynoate (73 mg) and hydroxylamine (50% aqueous solution, 18.2 mg) in methanol (1 mL) was added 2 mol/L aqueous sodium hydroxide solution (0.166 mL), and this mixture was stirred at room temperature for 64 hours. To the reaction mixture were added water, ethyl acetate, and 2 mol/L hydrochloric acid (0.230 mL). The organic layer was separated. This organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (33 mg). 1H-NMR (DMSO-d6) δ ppm: 3.77 (3H, s), 4.34 (2H, s), 6.51 (1H, s), 6.60-6.68 (1H, m), 6.87 (1H, d, J=2.3 Hz), 7.24-7.43 (3H, m), 7.44-7.54 (2H, m), 7.64-7.73 (1H, m), 7.76-7.87 (3H, m), 11.16 (1H, s), 11.47 (1H, s).

Provenance & Evidence