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

HRID 1749544ノート

反応式

HRID 1749544 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-c64fc0ccea2c40abb7c0c939db73dbe3
出典データセット
uspto-grants-2015_10
特許番号
US09156798B2

反応ノート

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