반응 #2487464

반응 방정식

hydrochloric acid

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

methanesulfonamide

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

→

title compound

수율 15.9%

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

수율 15.9%

용매

dichloromethane

반응 조건

후처리

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

실험 절차

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).

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