Methyl iodide → Tert-butyl N-[2-(1-methyl-1H-indol-3-YL)ethyl]carbamate
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:2]1.[H-].[Na+].I[CH3:23]>C1COCC1>[CH3:23][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[CH:2]1Participants
Procedure
To a solution of tert-butyl (2-(1H-indol-3-yl)ethyl)carbamate (4.70 g, 18.01 mmol) in anhydrous THF (50 mL) was added sodium hydride (800 mg, 20 mmol, 60% in mineral oil) at 0° C. under nitrogen. After the resulting reaction mixture was stirred at room temperature for 15 min, iodomethane (2.84 g, 20 mmol) in THF (15 mL) was added slowly at 0° C. The resulting mixture was stirred at room temperature for 3 h and quenched with saturated aqueous ammonium chloride solution. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. Concentration under vacuum gave the crude product, which was purified by silica gel column chromatography (0.6% MeOH in DCM) to afford the title compound (4 g, 14.6 mmol, 80% yield) as a brown solid. MS (ESI) m/z 275.1 [M+H]+.
Workup
- customAfter the resulting reaction mixture
- stirringThe resulting mixture was stirred at room temperature for 3 h
- customquenched with saturated aqueous ammonium chloride solution
- extractionThe aqueous layer was extracted with ethyl acetate
- washThe combined organic layers were washed with brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationConcentration under vacuum
- customgave the crude product, which
- customwas purified by silica gel column chromatography (0.6% MeOH in DCM)
Sources & evidence
- ORD record
- ord-c64fc0ccea2c40abb7c0c939db73dbe3
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156798B2
Reaction notes
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