Potassium Hydroxide → HCID 11638529, compound

HRID 490438Notes

Reaction equation

HRID 490438 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]([CH3:14])[CH:7]=[C:6]2[C:15]1[N:25](S(C2C=CC(C)=CC=2)(=O)=O)[C:18]2[N:19]=[CH:20][CH:21]=[C:22]([C:23]#[N:24])[C:17]=2[CH:16]=1.[OH-].[K+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]([CH3:14])[CH:7]=[C:6]2[C:15]1[NH:25][C:18]2[N:19]=[CH:20][CH:21]=[C:22]([C:23]#[N:24])[C:17]=2[CH:16]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 67147451HCID 67147451, compound

Product 1

HCID 11638529HCID 11638529, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 0.14 g of 2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile in 1.3 ml of a 5 N aqueous potassium hydroxide solution and 5 ml of methanol is brought to a temperature in the region of 60° C. for approximately 30 minutes. After returning to around 20° C., the insoluble material is filter-dried, and washed with water until a neutral pH is obtained. The insoluble material is purified by flash chromatography on a silica column [eluent: dichloromethane/methanol (98/2 by volume)]. 0.05 g of 2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile is obtained in the form of a solid, the characteristics of which are as follows:

Workup

  1. customAfter returning to around 20° C.
  2. customthe insoluble material is filter-dried
  3. washwashed with water until a neutral pH
  4. customis obtained
  5. customThe insoluble material is purified by flash chromatography on a silica column [eluent: dichloromethane/methanol (98/2 by volume)]

Sources & evidence

ORD record
ord-dba5a3daad1540fc837ad1c8a7ed75bc
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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