Reacción #2487464

Ecuación de reacción

hydrochloric acid

6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxylic acid

methanesulfonamide

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

→

title compound

Rendimiento 15.9%

N-(Methanesulfonyl)-6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxamide

Rendimiento 15.9%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirred vigorously
2. 2
   OtroThe organic layer was separated
3. 3
   Secadodried over anhydrous sodium sulfate
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   OtroThe residue was purified by silica gel column chromatography (eluting solvent: dichloromethane-methanol)
6. 6
   OtroThe solvent was removed under reduced pressure
7. 7
   OtroThe residue was recrystallized from ethanol

Procedimiento

Under an argon atmosphere, to a solution of 6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxylic acid (84 mg) in dichloromethane (2.3 mL) were added methanesulfonamide (22 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (45 mg), and 4-dimethylaminopyridine (29 mg). This mixture was stirred for 66 hours at room temperature. To the reaction mixture, 1 mol/L hydrochloric acid was added and stirred vigorously. The organic layer was separated, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: dichloromethane-methanol). The solvent was removed under reduced pressure. The residue was recrystallized from ethanol to obtain the title compound (16 mg). 1H-NMR (CDCl3) δ ppm: 3.38 (3H, s), 3.87 (3H, s), 5.49 (2H, s), 6.64 (1H, d, J=0.5 Hz), 6.84 (1H, dd, J=2.4, 8.9 Hz), 6.90-6.95 (1H, m), 7.05 (1H, d, J=8.9 Hz), 7.16 (1H, d, J=2.4 Hz), 7.30-7.50 (5H, m), 7.76 (1H, t, J=7.8 Hz), 8.00-8.10 (1H, m), 10.01 (1H, br s).

Fuente