反应详情

Under an argon atmosphere, to a suspension of 6-(6-methoxy-2-thiophen-3-yl-1H-indol-3-ylmethyl)pyridine-2-carboxylic acid (45.5 mg) in dichloromethane (0.6 mL) were added methane sulfonamide (11.9 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (23.9 mg), and 4-dimethylaminopyridine (15.3 mg), and this mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated under reduced pressure. To the residue was added 10% aqueous citric acid solution, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine successively, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. To the residue was added ethanol, and this suspension was heated to reflux for 45 minutes to give a solution. This solution was left to be cooled. The precipitate was collected by filtration and dried under reduced pressure to obtain the title compound (21.9 mg). 1H-NMR (DMSO-d6) δ ppm: 3.38 (3H, s), 3.77 (3H, s), 4.47 (2H, s), 6.65 (1H, dd, J=2.3, 8.6 Hz), 6.85 (1H, d, J=2.3 Hz), 7.27-7.35 (1H, m), 7.42 (1H, d, J=8.6 Hz), 7.56 (1H, dd, J=1.3, 5.0 Hz), 7.67 (1H, dd, J=3.0, 5.0 Hz), 7.81-7.91 (3H, m), 11.17 (1H, s), 11.42-11.66 (1H, br).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionTo the residue was added 10% aqueous citric acid solution
3. extractionfollowed by extraction with ethyl acetate
4. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine successively
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. additionTo the residue was added ethanol
8. temperaturethis suspension was heated
9. temperatureto reflux for 45 minutes
10. customto give a solution
11. waitThis solution was left
12. temperatureto be cooled
13. filtrationThe precipitate was collected by filtration
14. customdried under reduced pressure