Sodium Iodide → HCID 67147497, compound

HRID 490419Notes

Reaction equation

HRID 490419 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=2)[C:7]([C:18]2[N:26]([S:27]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[C:21]3=[N:22][CH:23]=[CH:24][CH:25]=[C:20]3[CH:19]=2)=[CH:6]1.[I-:37].[Na+]>C(C(C)=O)C>[I:37][CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=2)[C:7]([C:18]2[N:26]([S:27]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[C:21]3=[N:22][CH:23]=[CH:24][CH:25]=[C:20]3[CH:19]=2)=[CH:6]1

Participants

4

Reactant 2

HCID 5238Sodium Iodide2×HCID 67147566HCID 67147566, compound

Product 1

HCID 67147497HCID 67147497, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2-[1-(3-Chloropropyl)-5,6-dimethoxy-1H-indol-3-yl]-1-(toluene-4-sulfonyl)—1H-pyrrolo[2,3-b]pyridine (0.395 g; 753.8 μmol) and sodium iodide (0.169 g; 1.13 mmol) in methyl ethyl ketone (10 ml) are placed in a 50 ml single-necked flask, at reflux. After 16 hours, sodium iodide (0.169 g; 1.13 mmol) is added and reflux is maintained for a further 5 hours. The reaction mixture is evaporated under reduced pressure and the residue is then dissolved in 50 ml of ethyl acetate, transferred into a separating funnel and washed with 2 times 30 ml 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 silica gel (10 μg, silica 20-40 μm), elution being carried out at 10 ml/min with a mixture of cyclohexane and ethyl acetate (70/30; v/v). The fractions containing the expected compound are combined and evaporated to give 2-[1-(3-iodopropyl)-5,6-dimethoxy-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine in the form of an amorphous solid (0.287 g, 62%), the characteristics of which are as follows:

Workup

  1. temperatureat reflux
  2. temperaturereflux
  3. temperatureis maintained for a further 5 hours
  4. customThe reaction mixture is evaporated under reduced pressure
  5. dissolutionthe residue is then dissolved in 50 ml of ethyl acetate
  6. customtransferred into a separating funnel
  7. washwashed with 2 times 30 ml 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 silica gel (10 μg, silica 20-40 μm), elution
  14. additionbeing carried out at 10 ml/min with a mixture of cyclohexane and ethyl acetate (70/30; v/v)
  15. additionThe fractions containing the expected compound
  16. customevaporated

Sources & evidence

ORD record
ord-076592a74cc64aeeb530d71462b837a0
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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