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Methyl iodide → [1-(3,5-difluoro-benzyl)-3-(2-nitro-phenylsulfanyl)-1H-indol-6-yl]-methyl-amine

HRID 1158838
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HRID 1158838 반응식
IC.[F:3][C:4]1[CH:5]=[C:6]([CH:28]=[C:29]([F:31])[CH:30]=1)[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=2)[C:10]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N+:25]([O-:27])=[O:26])=[CH:9]1.[C:32](=O)([O-])[O-].[Na+].[Na+]>C(O)C.O1CCCC1>[F:3][C:4]1[CH:5]=[C:6]([CH:28]=[C:29]([F:31])[CH:30]=1)[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH:17][CH3:32])[CH:15]=2)[C:10]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N+:25]([O-:27])=[O:26])=[CH:9]1
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HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 594638551-(3,5-Difluoro-benzyl)-3-(2-nitro-phenylsulfanyl)-1H-indol-6-ylamine

생성물 1

HCID 66842175[1-(3,5-difluoro-benzyl)-3-(2-nitro-phenylsulfanyl)-1H-indol-6-yl]-methyl-amine수율 25%

시약·촉매·용매 2

HCID 702Ethanol용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

Iodomethane (0.568 ml, 9.12 mmol) was added to a solution of 1-(3,5-difluoro-benzyl)-3-(2-nitro-phenylsulfanyl)-1H-indol-6-ylamine (Example 15a; 2.5 g, 6.1 mmol) in a mixture of ethanol and tetrahydrofuran containing sodium carbonate (0.657 g, 6.08 mmol). The reaction mixture was heated under reflux overnight and concentrated. Water was added and the product was extracted into ethyl acetate. The combined organic phases were washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography (heptane/ethyl acetate 8:2) afforded [1-(3,5-difluoro-benzyl)-3-(2-nitro-phenylsulfanyl)-1H-indol-6-yl]-methyl-amine (0.647 g) and [1-(3,5-difluoro-benzyl-3-(2-nitro-phenylsulfanyl)-1H-indol-6-yl]-dimethyl-amine (0.815 g). 1H-NMR (CDCl3) δ 8.26 (dd, 1H, J=8.2 and 1.2 Hz), 7.35 (d, 1H, J=8.6 Hz), 7.27 (ddd, 1H, J=8.2, 7.4 and 1.2 Hz), 7.25 (s, 1H), 7.17 (ddd, 1H, J=8.2, 7.4 and 1.2 Hz), 7.03 (dd, 1H, J=8.2 and 1.2 Hz), 6.78 (dd, 1H, J=8.6 and 2.3 Hz), 6.74 (tt, 1H, J=8.6 and 2.3 Hz), 6.68 (m, 2H), 6.48 (d, 1H, J=2.3 Hz), 5.29 (s, 2H), 2.95 (s, 6H).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationconcentrated
  4. additionWater was added
  5. extractionthe product was extracted into ethyl acetate
  6. washThe combined organic phases were washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6c0a7f08295f4cee86c4cf8e5c9ca6bd
출처 데이터셋
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07812036B2

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