Sodium Hydroxide → 6-(6-Methoxy-2-thiophen-3-yl-1H-indol-3-ylmethyl)pyridine-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 6-(6-methoxy-2-thiophen-3-yl-1H-indol-3-ylmethyl)pyridine-2-carboxylate (936 mg) in tetrahydrofuran/methanol (14.7 mL/6.3 mL) was added 2 mol/L aqueous sodium hydroxide solution (3.71 mL) at room temperature, and this mixture was stirred at 60° C. for 2 hours. The reaction mixture was left to be cooled and concentrated under reduced pressure. The residue was suspended in water (30 mL) and the resulting mixture was acidified by the addition of 1 mol/L hydrochloric acid (7.8 mL). After stirring at room temperature for 1 hour, the precipitate was collected by filtration, washed with water, and then dried under reduced pressure. The suspension of the solid in ethanol was heated under reflux to give a solution. The solution was left to be cooled. The precipitate was collected by filtration and dried under reduced pressure to obtain the title compound (547 mg). 1H-NMR (DMSO-d6) δ ppm: 3.77 (3H, s), 4.37 (2H, s), 6.64 (1H, dd, J=2.3, 8.8 Hz), 6.85 (1H, d, J=2.3 Hz), 7.37 (1H, dd, J=1.5, 7.3 Hz), 7.42 (1H, d, J=8.8 Hz), 7.57 (1H, dd, J=1.3, 5.0 Hz), 7.67 (1H, dd, J=2.8, 5.0 Hz), 7.77-7.88 (2H, m), 8.09 (1H, dd, J=1.3, 2.8 Hz), 11.13 (1H, s), 12.60-13.70 (1H, br).

Provenance & Evidence