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Sodium hydride → 3-[1-(4-Acetoxymethyl-3-(2-(trimethylsilyl)ethoxymethoxy)benzyl)-indol-3-yl]-4-(1-methyl-indol-3-yl)furan-2,5-dione

HRID 1859199
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HRID 1859199 반응식
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:26])[O:13][C:14](=[O:25])[C:15]=2[C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)=[CH:3]1.[H-].[Na+].Br[CH2:30][C:31]1[CH:41]=[CH:40][C:34]([CH2:35][O:36][C:37](=[O:39])[CH3:38])=[C:33]([O:42][CH2:43][O:44][CH2:45][CH2:46][Si:47]([CH3:50])([CH3:49])[CH3:48])[CH:32]=1.[Cl-].[NH4+]>CN(C)C=O.O.C(OCC)(=O)C>[C:37]([O:36][CH2:35][C:34]1[CH:40]=[CH:41][C:31]([CH2:30][N:18]2[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:16]([C:15]3[C:14](=[O:25])[O:13][C:12](=[O:26])[C:11]=3[C:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:2]([CH3:1])[CH:3]=3)=[CH:17]2)=[CH:32][C:33]=1[O:42][CH2:43][O:44][CH2:45][CH2:46][Si:47]([CH3:50])([CH3:49])[CH3:48])(=[O:39])[CH3:38]
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참가 물질

8

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 148557143-(1-Methyl-indol-3-yl)-4-(indol-3-yl)-furan-2,5-dioneHCID 53743209Acetic acid 4-bromomethyl-2-(2-(trimethylsilyl)ethoxymethoxy)benzyl ester

생성물 1

HCID 221232583-[1-(4-Acetoxymethyl-3-(2-(trimethylsilyl)ethoxymethoxy)benzyl)-indol-3-yl]-4-(1-methyl-indol-3-yl)furan-2,5-dione

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

3-(1-Methyl-indol-3-yl)-4-(indol-3-yl)-furan-2,5-dione (2.21 g, 0.61 mmol) and sodium hydrid (55-60% dispersion in oil, 0.031 g, 0.76 mmol) were dissolved in dry dimethylformamide and stirred for 20 minutes at ambient temperature before adding acetic acid 4-bromomethyl-2-(2-(trimethylsilyl)ethoxymethoxy)benzyl ester (0.25 g, 0.64 mmol). The reaction was allowed to proceed for 20 hours before adding ethyl acetate (20 mL), water (5 mL) and saturated aqueous ammonium chloride (5 mL). The phases were separated and the aqueous phase extracted with ethyl acetate (20 mL). The combined organic phases were washed with water (2×20 mL), and dried over Na2SO4. Removal of the solvent furnished crude 3-[1-(4-acetoxymethyl-3-(2-(trimethylsilyl)ethoxymethoxy)benzyl)-indol-3-yl]-4-(1-methyl-indol-3-yl)furan-2,5-dione which was dissolved in dimethylformamide (3 mL) and ammonium hydroxide (9 mL). Heating to 75° C. in a sealed tube for four hours gave, after extraction with ethyl acetate and chromatography (ethyl acetate/heptane:60/40), 98 mg of the sub-title compound as a red solid.

후처리

  1. waitto proceed for 20 hours
  2. customThe phases were separated
  3. extractionthe aqueous phase extracted with ethyl acetate (20 mL)
  4. washThe combined organic phases were washed with water (2×20 mL)
  5. dry with materialdried over Na2SO4
  6. customRemoval of the solvent

출처 및 근거

ORD 기록
ord-a2afa198753a481e8b53135593224297
출처 데이터셋
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06153641

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