Sodium Iodide → HCID 67147570, compound

HRID 2426876Notes

Reaction equation

HRID 2426876 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:15]3[N:23]([S:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)(=[O:26])=[O:25])[C:18]4=[N:19][CH:20]=[CH:21][CH:22]=[C:17]4[CH:16]=3)=[CH:10][N:11]2[CH3:14])=[CH:7][C:6]=1[O:34][CH3:35].[I-:36].[Na+].C1CCCCC1.C(OCC)(=O)C>C(C(C)=O)C>[I:36][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:15]3[N:23]([S:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)(=[O:26])=[O:25])[C:18]4=[N:19][CH:20]=[CH:21][CH:22]=[C:17]4[CH:16]=3)=[CH:10][N:11]2[CH3:14])=[CH:7][C:6]=1[O:34][CH3:35]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 21867204Cyclohexane ethylacetateHCID 67147439HCID 67147439, compound

Product 1

HCID 67147570HCID 67147570, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 2-[6-(2-chloroethoxy)-5-methoxy-1-methyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.660 g, 1,294 μmol) in methyl ethyl ketone (10 ml) is placed in a 50 ml single-necked flask and sodium iodide (0.29 g; 1.941 mmol) is then added. The reaction mixture is refluxed for 16 hours. Analysis by thin layer chromatography (50/50 cyclohexane/ethyl acetate) shows that the reaction has come to an end. After returning to 20° C., the reaction mixture is evaporated under reduced pressure and the residue is taken up in a mixture of water (50 ml) and dichloromethane (50 ml), which is separated by settling out; the organic extract is washed with water (30 ml) and dried over magnesium sulfate. After evaporation, the compound obtained is purified by chromatography on silica gel (cartridge FC-10-Si-BP-Sup, 10 g of silica with a particle size of 15-35 μm, elution being carried out with a 70/30 mixture of cyclohexane/ethyl acetate). The fractions containing the expected compound are combined and then evaporated under reduced pressure, giving 2-[6-(2-iodoethoxy)-5-methoxy-1-methyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.695 g; 89%) the characteristics of which are as follows:

Workup

  1. temperatureThe reaction mixture is refluxed for 16 hours
  2. customAfter returning to 20° C.
  3. customthe reaction mixture is evaporated under reduced pressure
  4. additionthe residue is taken up in a mixture of water (50 ml) and dichloromethane (50 ml), which
  5. customis separated
  6. extractionthe organic extract
  7. washis washed with water (30 ml)
  8. dry with materialdried over magnesium sulfate
  9. customAfter evaporation
  10. customthe compound obtained
  11. customis purified by chromatography on silica gel (cartridge FC-10-Si-BP-Sup, 10 g of silica
  12. washwith a particle size of 15-35 μm, elution
  13. additionbeing carried out with a 70/30 mixture of cyclohexane/ethyl acetate)
  14. additionThe fractions containing the expected compound
  15. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8c85389dc6ef4cf0a02b95329d3f03f6
Source dataset
uspto-grants-2011_06
Patent number
US07968566B2

Reaction notes

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