Water → 1-BOC-5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-7-nitro-1H-indole-2-carboxylic acid methyl ester

HRID 1045847노트

반응식

HRID 1045847 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([CH2:14]Br)=[CH:9][C:8]=2[N+:16]([O-:18])=[O:17])=[O:4].[C:26]1(=[O:36])[NH:30][C:29](=[O:31])[C:28]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:27]12.[K].O>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([CH2:14][N:30]1[C:26](=[O:36])[C:27]3[C:28](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:29]1=[O:31])=[CH:9][C:8]=2[N+:16]([O-:18])=[O:17])=[O:4]

참가 물질

5

반응물 3

HCID 962WaterHCID 24194345Phthalimide potassium saltHCID 594480901-BOC-5-bromomethyl-7-nitro-indole-2-carboxylic acid methyl ester

생성물 1

HCID 684852561-BOC-5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-7-nitro-1H-indole-2-carboxylic acid methyl ester수율 66%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

1-BOC-5-bromomethyl-7-nitro-indole-2-carboxylic acid methyl ester (4.9 g, 11.4 mmol) prepared in Step B of Preparation 37 was dissolved in N,N-dimethylformamide (50 mL). Potassium phthalimide (2.7 g, 14.8 mmol) was added thereto, and the mixture was stirred for 4 h at room temperature. Water was added to quench the reaction. The reaction mixture was extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residue was purified by column chromatography to give the title compound (3.6 g, Yield 66%).

후처리

  1. customto quench
  2. customthe reaction
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customthe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-c66c1cf01345410cafadaeca4601856f
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569307B2

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