Hydrazine hydrate (1:1) → HCID 68163521, compound

Participants

Reaction Steps

To a solution of methyl 6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxylate (70 mg) in methanol (1.2 mL) and tetrahydrofuran (0.4 mL) was added hydrazine monohydrate (0.091 mL). This mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (1 mL), and then 1,1′-carbonyldiimidazole (46 mg) was added thereto at room temperature. The mixture was stirred at room temperature for 2 hours. To the reaction mixture was added 1 mol/L hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, 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 (48 mg). 1H-NMR (DMSO-d6) δ ppm: 3.77 (3H, s), 5.52 (2H, s), 6.62 (1H, s), 6.65-6.80 (2H, m), 7.13 (1H, d, J=2.5 Hz), 7.25 (1H, d, J=8.9 Hz), 7.35-7.50 (3H, m), 7.55-7.65 (2H, m), 7.75 (1H, d, J=7.9 Hz), 7.85 (1H, t, J=7.9 Hz), 12.78 (1H, br s). ESI-MS (m/z): 399 (M+H)+

Provenance & Evidence