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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
Notes
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Reaction equation

HRID 1859199 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a2afa198753a481e8b53135593224297
Source dataset
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06153641

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes