Sodium Iodide → 2-[6-(3-Iodopropoxy)-5-methoxy-1-methyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 2426878Notes

Reaction equation

HRID 2426878 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([C:10]([C:16]3[N:24]([S:25]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=4)(=[O:27])=[O:26])[C:19]4=[N:20][CH:21]=[CH:22][CH:23]=[C:18]4[CH:17]=3)=[CH:11][N:12]2[CH3:15])=[CH:8][C:7]=1[O:35][CH3:36].[I-:37].[Na+].C1CCCCC1.C(OCC)(=O)C>C(C(C)=O)C.ClCCl>[I:37][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([C:10]([C:16]3[N:24]([S:25]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=4)(=[O:27])=[O:26])[C:19]4=[N:20][CH:21]=[CH:22][CH:23]=[C:18]4[CH:17]=3)=[CH:11][N:12]2[CH3:15])=[CH:8][C:7]=1[O:35][CH3:36]

Participants

6

Reactant 3

HCID 5238Sodium Iodide2×HCID 21867204Cyclohexane ethylacetateHCID 67147656HCID 67147656, compound

Product 1

HCID 671476092-[6-(3-Iodopropoxy)-5-methoxy-1-methyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridineYield 75.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 2-[6-(3-chloropropoxy)-5-methoxy-1-methyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.415 g; 792 μmol) in methyl ethyl ketone (10 ml) is placed in a 50 ml single-necked flask and sodium iodide (0.178 g; 1.18 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 starting compound is still present. Additional sodium iodide (0.178 g; 1.18 mmol) is introduced and the reflux is maintained for 3 hours. After returning to 20° C., the precipitate is dissolved in dichloromethane (200 ml) and then washing with water (50 ml) and drying over magnesium sulfate are carried out. After evaporation, the residue is taken up in ethyl acetate (20 ml); the insoluble material is removed and the filtrate is then evaporated under reduced pressure. 2-[6-(3-Iodopropoxy)-5-methoxy-1-methyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.367 g; 75%) is isolated, the characteristics of which are as follows:

Workup

  1. temperatureThe reaction mixture is refluxed for 16 hours
  2. temperaturethe reflux is maintained for 3 hours
  3. customAfter returning to 20° C.
  4. washwashing with water (50 ml)
  5. dry with materialdrying over magnesium sulfate
  6. customAfter evaporation
  7. customthe insoluble material is removed
  8. customthe filtrate is then evaporated under reduced pressure

Sources & evidence

ORD record
ord-f2f8facae75d42f8be7ae25448d76d98
Source dataset
uspto-grants-2011_06
Patent number
US07968566B2

Reaction notes

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