Water → HCID 67147635, compound

HRID 2426890Notes

Reaction equation

HRID 2426890 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[C:12]([O:14][CH3:15])[CH:13]=1)[N:10]([CH3:16])[CH:9]=[C:8]2[C:17]1[N:25](S(C2C=CC(C)=CC=2)(=O)=O)[C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:19]2[CH:18]=1.O>CO>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[C:12]([O:14][CH3:15])[CH:13]=1)[N:10]([CH3:16])[CH:9]=[C:8]2[C:17]1[NH:25][C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:19]2[CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 67147620HCID 67147620, compound

Product 1

HCID 67147635HCID 67147635, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

3.3 ml of a 5N aqueous potassium hydroxide solution are added to a solution of 0.31 g of 2-(5,7-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine in 20 ml of methanol. The mixture is heated at around 80° C. for approximately 18 hours. The reaction medium is run into a mixture of 100 ml of ice plus water, and extracted with three times 75 ml of ethyl acetate. The combined organic phases are washed with 100 ml of water and then with 100 ml of a saturated aqueous sodium chloride solution, 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: dichloromethane]. 0.073 g of 2-(5,7-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine is obtained in the form of a solid, the characteristics of which are as follows:

Workup

  1. extractionextracted with three times 75 ml of ethyl acetate
  2. washThe combined organic phases are washed with 100 ml of water
  3. dry with materialwith 100 ml of a saturated aqueous sodium chloride solution, dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (13 kPa)
  6. customThe residue is purified by flash chromatography on a silica column [eluent: dichloromethane]

Sources & evidence

ORD record
ord-ce95eb74f5e64027bb10e19e1d0ecebc
Source dataset
uspto-grants-2011_06
Patent number
US07968566B2

Reaction notes

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