Methyl iodide → HCID 69096830, compound

Participants

Reaction Steps

To a solution of methyl 6-(6-methyl-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxylate (100 mg) in N,N-dimethylformamide (2 mL) was added sodium hydride (min. 55% in oil, 13 mg) under ice-cooling, and this mixture was stirred at room temperature for 30 minutes. Then, methyl iodide (0.026 mL) was added thereto, followed by stirring at room temperature overnight. To the reaction mixture were added ethyl acetate and water, and the organic layer was separated. The 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 aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (35.3 mg). 1H-NMR (CDCl3) δ ppm: 2.51 (3H, s), 3.62 (3H, s), 4.02 (3H, s), 4.36 (2H, s), 6.88-6.95 (1H, m), 7.12-7.20 (2H, m), 7.29 (1H, d, J=8.0 Hz), 7.33-7.49 (5H, m), 7.58 (1H, t, J=7.8 Hz), 7.88-7.95 (1H, m).

Provenance & Evidence