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Potassium Hydroxide → 2-[5,6-dimethoxy-1-(2-morpholin-4-ylethyl)-1H-indol-3-yl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine

HRID 490455
Notes
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Reaction equation

HRID 490455 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][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[CH:9]=[C:8]2[C:24]1[N:33](S(C2C=CC(C)=CC=2)(=O)=O)[C:27]2=[N:28][CH:29]=[C:30]([F:32])[CH:31]=[C:26]2[CH:25]=1>O.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][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[CH:9]=[C:8]2[C:24]1[NH:33][C:27]2=[N:28][CH:29]=[C:30]([F:32])[CH:31]=[C:26]2[CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 671475492-[5,6-dimethoxy-1-(2-morpholin-4-ylethyl)-1H-indol-3-yl]-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 116547592-[5,6-dimethoxy-1-(2-morpholin-4-ylethyl)-1H-indol-3-yl]-5-fluoro-1H-pyrrolo[2,3-b]pyridineYield 60.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 962
Water
Solvent

Procedure

A solution of 2.08 g of potassium hydroxide in 7 ml of water is added to a solution of 0.83 g of 2-[5,6-dimethoxy-1-(2-morpholin-4-ylethyl)-1H-indol-3-yl]-5-fluoro-1-(toluene-4-sulfonyl)—1H-pyrrolo[2,3-b]pyridine in 100 ml of methanol brought to reflux. The mixture is agitated at reflux for 3 hours 30 minutes. After returning to around 20° C., the mixture is concentrated to dryness under reduced pressure (13 kPa). The residue is taken up with 50 ml of water and extracted with three times 80 ml of dichloromethane. The combined organic phases are dried over magnesium sulfate, filtered, and concentrated to dryness under reduced pressure (13 kPa). The residue is purified by flash chromatography on a silica column [eluent: ethyl acetate/methanol (90/10 by volume)]. 0.37 g of 2-[5,6-dimethoxy-1-(2-morpholin-4-ylethyl)-1H-indol-3-yl]-5-fluoro-1H-pyrrolo[2,3-b] pyridine is obtained in the form of a solid, the characteristics of which are as follows:

Workup

  1. temperatureto reflux
  2. temperatureat reflux for 3 hours 30 minutes
  3. customAfter returning to around 20° C.
  4. concentrationthe mixture is concentrated to dryness under reduced pressure (13 kPa)
  5. extractionextracted with three times 80 ml of dichloromethane
  6. dry with materialThe combined organic phases are dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (13 kPa)
  9. customThe residue is purified by flash chromatography on a silica column [eluent: ethyl acetate/methanol (90/10 by volume)]

Sources & evidence

ORD record
ord-eb29756fda674855883be13cb01c2c28
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