Réaction #2487480

Équation de réaction

hydrochloric acid

6-[2-(2,5-difluorophenyl)-5-methoxyindol-1-ylmethyl]pyridine-2-carboxylic acid

cyanamide

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

→

title compound

Rendement 74.1%

N-Cyano-6-[2-(2,5-difluorophenyl)-5-methoxyindol-1-ylmethyl]pyridine-2-carboxamide

Rendement 74.1%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Extractionfollowed by extraction with dichloromethane
2. 2
   LavageThe organic layer was washed with 1 mol/L hydrochloric acid and saturated brine successively
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: ethyl acetate-methanol)

Mode opératoire

To a solution of 6-[2-(2,5-difluorophenyl)-5-methoxyindol-1-ylmethyl]pyridine-2-carboxylic acid (70 mg) in dichloromethane (1.8 mL) were successively added cyanamide (8.2 mg), 4-dimethylaminopyridine (48 mg), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (75 mg). This mixture was stirred for 35 hours at room temperature. To the reaction mixture was added 1 mol/L hydrochloric acid, followed by extraction with dichloromethane. The organic layer was washed with 1 mol/L hydrochloric acid and saturated brine successively, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-methanol) to obtain the title compound (55 mg). 1H-NMR (DMSO-d6) δ ppm: 3.77 (3H, s), 5.37 (2H, s), 6.45 (1H, d, J=7.4 Hz), 6.66 (1H, s), 6.79 (1H, dd, J=2.4, 8.9 Hz), 7.10-7.45 (4H, m), 7.50-7.85 (3H, m). ESI-MS (m/z): 419 (M+H)+

Source