Réaction #2487464

Équation de réaction

hydrochloric acid

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

methanesulfonamide

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

→

title compound

Rendement 15.9%

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

Rendement 15.9%

Solvants

dichloromethane

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source