Sodium Iodide → HCID 67147570, compound

HRID 490479Notes

Reaction equation

HRID 490479 reaction equation
[I-:1].[Na+].[CH3:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:17][CH3:18])=[C:10]([O:13][CH2:14][CH2:15]Cl)[CH:11]=2)[C:6]([C:19]2[N:27]([S:28]([C:31]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=3)(=[O:30])=[O:29])[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[CH:20]=2)=[CH:5]1>CC(=O)CC>[CH3:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:17][CH3:18])=[C:10]([O:13][CH2:14][CH2:15][I:1])[CH:11]=2)[C:6]([C:19]2[N:27]([S:28]([C:31]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=3)(=[O:30])=[O:29])[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[CH:20]=2)=[CH:5]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 67147439HCID 67147439, compound

Product 1

HCID 67147570HCID 67147570, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

0.260 g of sodium iodide is added to a solution of 0.59 g of 2-[1-methyl-5-methoxy-6-(2-chloroethoxy)-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine in 42 ml of 2-butanone, under an inert argon atmosphere at a temperature in the region of 20° C. The reaction medium is refluxed for 24 hours. After cooling, the reaction medium is concentrated under reduced pressure. The residue obtained is purified by flash-pack chromatography (silica, dichloromethane as eluent). The fractions containing the product are concentrated under reduced pressure. 0.565 g of 2-[1-methyl-5-methoxy-6-(2-iodoethoxy)-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine is thus obtained, the characteristics of which are as follows:

Workup

  1. temperatureThe reaction medium is refluxed for 24 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction medium is concentrated under reduced pressure
  4. customThe residue obtained
  5. customis purified by flash-pack chromatography (silica, dichloromethane as eluent)
  6. additionThe fractions containing the product
  7. concentrationare concentrated under reduced pressure

Sources & evidence

ORD record
ord-6f0e62f8a8854b0794d97369702bbcd5
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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