Reaction #2487464

Reaction equation

hydrochloric acid

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

methanesulfonamide

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

→

title compound

Yield 15.9%

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

Yield 15.9%

Solvents

dichloromethane

Conditions

Workup

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

Procedure

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