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Water → HCID 67147443, compound

HRID 490424
Notes
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Reaction equation

HRID 490424 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[NH:10][CH:9]=[C:8]2[C:16]1[N:24]([S:25]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)(=[O:27])=[O:26])[C:19]2=[N:20][CH:21]=[CH:22][CH:23]=[C:18]2[CH:17]=1.[Si:35]([O:42][CH2:43][CH2:44]Br)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36].O>CN(C)C=O.C(OCC)(=O)C>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]([CH2:44][CH2:43][O:42][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[CH:9]=[C:8]2[C:16]1[N:24]([S:25]([C:28]2[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=2)(=[O:27])=[O:26])[C:19]2=[N:20][CH:21]=[CH:22][CH:23]=[C:18]2[CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 22477225HCID 22477225, compound

Product 1

HCID 67147443HCID 67147443, compound

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

0.049 g of sodium hydride (at 60%) is added to a solution of 0.5 g of 2-(5,6-dimethoxy-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine in 12.5 ml of anhydrous dimethylformamide, under an inert argon atmosphere at a temperature in the region of 20° C. Agitation is maintained at this temperature for 30 minutes. 0.264 ml of 2-tert-butyldimethylsilyloxyethyl bromide is added. The reaction medium is agitated at the same temperature for 16 hours. 25 ml of water and 20 ml of ethyl acetate are added. After separation by settling out, the organic phase is dried over sodium sulfate, filtered, and then concentrated under reduced pressure. The residue obtained is purified by flash chromatography (silica, 98/02 by volume dichloromethane/methanol as eluents, argon). The fractions containing the product are concentrated under reduced pressure. 0.47 g of 2-[5,6-dimethoxy-1-(2-tert-butyldimethylsilyloxyethyl)indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine is thus obtained, the characteristics of which are as follows:

Workup

  1. temperatureAgitation is maintained at this temperature for 30 minutes
  2. customAfter separation
  3. dry with materialthe organic phase is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customis purified by flash chromatography (silica, 98/02 by volume dichloromethane/methanol as eluents, argon)
  8. additionThe fractions containing the product
  9. concentrationare concentrated under reduced pressure

Sources & evidence

ORD record
ord-83136c0586994f66b28f49d185a07309
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07528147B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes