Methyl iodide → HCID 67147657, compound

HRID 2426945Notes

Reaction equation

HRID 2426945 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[NH:10][CH:9]=[C:8]2[C:16]1[N:25]([S:26]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[C:19]2=[N:20][CH:21]=[CH:22][C:23]([CH3:24])=[C:18]2[CH:17]=1.[CH3:36]I>CN(C)C=O.O>[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]([CH3:36])[CH:9]=[C:8]2[C:16]1[N:25]([S:26]([C:29]2[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=2)(=[O:27])=[O:28])[C:19]2=[N:20][CH:21]=[CH:22][C:23]([CH3:24])=[C:18]2[CH:17]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67147829HCID 67147829, compound

Product 1

HCID 67147657HCID 67147657, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.017 g of sodium hydride (60%) is added to a solution of 0.17 g of 2-[5,6-dimethoxy-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-4-methyl-1H-pyrrolo[2,3-b]pyridine in 7 cm3 of anhydrous dimethylformamide, under an inert atmosphere of argon at a temperature in the region of 20° C. After stirring for one hour at the same temperature, 0.025 cm3 of methyl iodide is added. Stirring is continued at this temperature for 4 hours. The reaction mixture is taken up in 50 cm3 of water and then extracted with 100 cm3 of ethyl acetate, and the aqueous phase is re-extracted with 2×50 cm3 of ethyl acetate. The combined organic phases are washed successively with 50 cm3 of saturated aqueous sodium chloride solution and then with 50 cm3 of distilled water. After separation of the phases by settling, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. The residue obtained is purified 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 dichloromethane/methanol mixture (95/05 by volume). The fractions containing the expected compound are combined and evaporated to give 2-[5,6-dimethoxy-1-methyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-4-methyl-1H-pyrrolo[2,3-b]pyridine in the form of a beige-colored solid (0.130 g, 72%), the characteristics of which are as follows:

Workup

  1. additionis added
  2. extractionextracted with 100 cm3 of ethyl acetate
  3. extractionthe aqueous phase is re-extracted with 2×50 cm3 of ethyl acetate
  4. washThe combined organic phases are washed successively with 50 cm3 of saturated aqueous sodium chloride solution
  5. customAfter separation of the phases
  6. dry with materialthe organic phase is dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue obtained
  10. customis purified on a Flash Chromabond RS 6 SiOH cartridge (3 g of silica)
  11. washThe elution
  12. additionThe fractions containing the expected compound
  13. customevaporated

Sources & evidence

ORD record
ord-908b9a7d41f94a79864646d6771ee556
Source dataset
uspto-grants-2011_06
Patent number
US07968566B2

Reaction notes

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