Water → HCID 67147709, compound

HRID 490422Notes

Reaction equation

HRID 490422 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.[CH3:35][O:36][CH2:37][CH2:38]Br.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]([CH2:38][CH2:37][O:36][CH3:35])[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

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 22477225HCID 22477225, compound

Product 1

HCID 67147709HCID 67147709, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.01 g of sodium hydride (60%) is added to a solution of 0.1 g of 2-[5,6-dimethoxy-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine in 2.5 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. 0.023 ml of bromoethyl methyl ether is added. The reaction medium is agitated at the same temperature for 16 hours. 3 ml of water and 3 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 on a flash-pack chromatography cartridge (silica, dichloromethane as eluent). The fractions containing the product are concentrated under reduced pressure. 0.082 g of 2-[5,6-dimethoxy-1-(2-methoxyethyl)-1H-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 on a flash-pack chromatography cartridge (silica, dichloromethane as eluent)
  8. additionThe fractions containing the product
  9. concentrationare concentrated under reduced pressure

Sources & evidence

ORD record
ord-94ab7e3380b74a4f926bfa5099641051
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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