Réaction #2487471

Équation de réaction

hydrochloric acid

water

methyl 6-[2-(butan-2-yl)-6-chloro-5-methoxyindol-1-ylmethyl]pyridine-2-carboxylate

sodium hydroxide

→

title compound

Rendement 98.6%

6-[2-(Butan-2-yl)-6-chloro-5-methoxyindol-1-ylmethyl]pyridine-2-carboxylic acid

Rendement 98.6%

Solvants

ethyl acetate

tetrahydrofuran

methanol

Conditions de réaction

Traitement

1. 1
   Autreto separate the organic layer
2. 2
   LavageThe organic layer was washed with water twice
3. 3
   Séchagedried over anhydrous sodium sulfate
4. 4
   Concentrationconcentrated under reduced pressure

Mode opératoire

To a solution of methyl 6-[2-(butan-2-yl)-6-chloro-5-methoxyindol-1-ylmethyl]pyridine-2-carboxylate (200 mg) in tetrahydrofuran (3.08 mL) and methanol (1.32 mL) was added 2 mol/L aqueous sodium hydroxide solution (0.775 mL) at room temperature, followed by stirring for 2.5 hours. To the reaction mixture was added 1 mol/L hydrochloric acid (1.55 mL). To the mixture were added water and ethyl acetate to separate the organic layer. The organic layer was washed with water twice, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain the title compound (190 mg). 1H-NMR (DMSO-d6) δ ppm: 0.77 (3H, t, J=7.4 Hz), 1.17 (3H, d, J=6.9 Hz), 1.40-1.70 (2H, m), 2.80-2.95 (1H, m), 3.83 (3H, s), 5.45-5.65 (2H, m), 6.30 (1H, s), 6.70 (1H, d, J=7.3 Hz), 7.20 (1H, s), 7.55 (1H, s), 7.80-7.95 (2H, m), 13.00-13.50 (1H, br).

Source