Potassium Hydroxide → HCID 67147719, compound

HRID 490423Notes

Reaction equation

HRID 490423 reaction equation
[OH-].[K+].[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]([CH2:16][CH2:17][OH:18])[CH:9]=[C:8]2[C:19]1[N:27](S(C2C=CC(C)=CC=2)(=O)=O)[C:22]2=[N:23][CH:24]=[CH:25][CH:26]=[C:21]2[CH:20]=1>CO>[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]([CH2:16][CH2:17][OH:18])[CH:9]=[C:8]2[C:19]1[NH:27][C:22]2=[N:23][CH:24]=[CH:25][CH:26]=[C:21]2[CH:20]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 67147623HCID 67147623, compound

Product 1

HCID 67147719HCID 67147719, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.65 ml of a 5N aqueous potassium hydroxide solution are added to a solution of 0.18 g of 2-{5,6-dimethoxy-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]indol-1-yl}ethanol in 10 ml of methanol, at a temperature in the region of 20° C. The reaction medium is refluxed for 4 hours. After cooling, the solid formed is filtered off through sintered glass, and washed twice with 3 ml of methanol and then five times with 5 ml of water. The solid is purified by flash-pack chromatography (silica, 95/05 by volume dichloromethane/methanol as eluents). 0.045 g of 2-[5,6-dimethoxy-3-(1H-pyrrolo[2,3-b]pyridin-2-yl)indol-1-yl]ethanol is obtained, the characteristics of which are as follows:

Workup

  1. temperatureThe reaction medium is refluxed for 4 hours
  2. temperatureAfter cooling
  3. customthe solid formed
  4. filtrationis filtered off through sintered glass
  5. washwashed twice with 3 ml of methanol
  6. customThe solid is purified by flash-pack chromatography (silica, 95/05 by volume dichloromethane/methanol as eluents)

Sources & evidence

ORD record
ord-0bcd2b5352904b46bb5da5413ad2a49f
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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