Sodium Iodide → HCID 67147418, compound

HRID 2426813Notes

Reaction equation

HRID 2426813 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[C:6]([C:17]2[N:25]([S:26]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[CH:18]=2)=[CH:5]1.[I-:36].[Na+]>C(C(C)=O)C>[I:36][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[C:6]([C:17]2[N:25]([S:26]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[CH:18]=2)=[CH:5]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 67147541HCID 67147541, compound

Product 1

HCID 67147418HCID 67147418, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 2-[1-(2-chloroethyl)-5,6-dimethoxy-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.331 g; 649 μmol), described in example 1, and sodium iodide (0.195 g; 1.298 mmol) in methyl ethyl ketone (5 ml) is placed in a 10 ml round-bottomed flask. The reaction mixture is brought to reflux for 16 hours. After evaporation, the product is taken up in a mixture of water (15 ml) and ethyl acetate (15 ml). After separation by settling out and extraction with ethyl acetate (2×15 ml), the organic extracts are combined, dried over magnesium sulfate, and then evaporated under reduced pressure. The evaporation residue is chromatographed on silica gel, elution being carried out with a mixture of cyclohexane and ethyl acetate (50/50). The fractions containing the expected compound are combined and evaporated, giving 2-[1-(2-iodoethyl)-5,6-dimethoxy-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.24 g; 69%), the characteristics of which are as follows:

Workup

  1. customis placed in a 10 ml round-bottomed flask
  2. temperatureto reflux for 16 hours
  3. customAfter evaporation
  4. additionthe product is taken up in a mixture of water (15 ml) and ethyl acetate (15 ml)
  5. customAfter separation
  6. extractionextraction with ethyl acetate (2×15 ml)
  7. dry with materialdried over magnesium sulfate
  8. customevaporated under reduced pressure
  9. customThe evaporation residue is chromatographed on silica gel, elution
  10. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (50/50)
  11. additionThe fractions containing the expected compound
  12. customevaporated

Sources & evidence

ORD record
ord-7f967dddcc6147868717e6672aa0a9e1
Source dataset
uspto-grants-2011_06
Patent number
US07968566B2

Reaction notes

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