Methyl iodide → Tert-butyl N-[2-(1-methyl-1H-indol-3-YL)ethyl]carbamate

HRID 1749544노트

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HRID 1749544 반응식
[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]1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 691825tert-Butyl (2-(1H-indol-3-yl)ethyl)carbamate

생성물 1

HCID 71202127Tert-butyl N-[2-(1-methyl-1H-indol-3-YL)ethyl]carbamate수율 81.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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]+.

후처리

  1. customAfter the resulting reaction mixture
  2. stirringThe resulting mixture was stirred at room temperature for 3 h
  3. customquenched with saturated aqueous ammonium chloride solution
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationConcentration under vacuum
  9. customgave the crude product, which
  10. customwas purified by silica gel column chromatography (0.6% MeOH in DCM)

출처 및 근거

ORD 기록
ord-c64fc0ccea2c40abb7c0c939db73dbe3
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156798B2

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