Potassium Hydroxide → HCID 46868160, compound

HRID 2426944Notes

Reaction equation

HRID 2426944 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]([CH3:16])[CH:9]=[C:8]2[C:17]1[N:26](S(C2C=CC(C)=CC=2)(=O)=O)[C:20]2=[N:21][CH:22]=[CH:23][C:24]([CH3:25])=[C:19]2[CH:18]=1>CO.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]([CH3:16])[CH:9]=[C:8]2[C:17]1[NH:26][C:20]2=[N:21][CH:22]=[CH:23][C:24]([CH3:25])=[C:19]2[CH:18]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67147657HCID 67147657, compound

Product 1

HCID 46868160HCID 46868160, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.3 cm3 of aqueous 5N potassium hydroxide solution are added to a solution of 0.13 g of 2-[5,6-dimethoxy-1-methyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-4-methyl-1H-pyrrolo[2,3-b]pyridine in 15 cm3 of methanol, at a temperature in the region of 20° C. The reaction medium is refluxed for about 18 hours. The reaction mixture is evaporated under reduced pressure and the residue thus obtained is dissolved in 100 cm3 of ethyl acetate, transferred into a separating funnel and washed with 50 cm3 of distilled water. The aqueous phase is re-extracted with twice 50 cm3 of ethyl acetate, and the combined organic phases are washed successively with 50 cm3 of saturated aqueous sodium chloride solution and 50 cm3 of distilled water. The organic extract is dried over magnesium sulfate, filtered and evaporated under reduced pressure to give the crude compound, which is purified by chromatography on a Flash Chromabond RS 6 SiOH cartridge (3 g of silica). The elution was performed at a flow rate of 10 cm3/min with a heptane/isopropanol mixture (70/30 by volume). The fractions containing the expected compound are combined and evaporated to give 2-[5,6-dimethoxy-1-methyl-1H-indol-3-yl]-4-methyl-1H-pyrrolo[2,3-b]pyridine in the form of a pasty yellow solid (0.008 g, 8%), the characteristics of which are as follows:

Workup

  1. temperatureThe reaction medium is refluxed for about 18 hours
  2. customThe reaction mixture is evaporated under reduced pressure
  3. customthe residue thus obtained
  4. customtransferred into a separating funnel
  5. washwashed with 50 cm3 of distilled water
  6. extractionThe aqueous phase is re-extracted with twice 50 cm3 of ethyl acetate
  7. washthe combined organic phases are washed successively with 50 cm3 of saturated aqueous sodium chloride solution and 50 cm3 of distilled water
  8. extractionThe organic extract
  9. dry with materialis dried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated under reduced pressure
  12. customto give the crude compound, which
  13. customis purified by chromatography on a Flash Chromabond RS 6 SiOH cartridge (3 g of silica)
  14. washThe elution
  15. additionThe fractions containing the expected compound
  16. customevaporated

Sources & evidence

ORD record
ord-de76fd7bf9f84351b83c020038c465e9
Source dataset
uspto-grants-2011_06
Patent number
US07968566B2

Reaction notes

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