Trimethylsilyl iodide → 5-methoxy-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-6-ol

HRID 490467Notes

Reaction equation

HRID 490467 reaction equation
C([O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([C:18]3[N:26]([S:27]([C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=4)(=[O:29])=[O:28])[C:21]4=[N:22][CH:23]=[CH:24][CH:25]=[C:20]4[CH:19]=3)=[CH:14][NH:15]2)=[CH:11][C:10]=1[O:37][CH3:38])C1C=CC=CC=1.C[Si](I)(C)C>C(#N)C>[CH3:38][O:37][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:9]=1[OH:8])[NH:15][CH:14]=[C:13]2[C:18]1[N:26]([S:27]([C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)(=[O:29])=[O:28])[C:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:20]2[CH:19]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 224773972-(6-benzyloxy-5-methoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 671475805-methoxy-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-6-olYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-(6-benzyloxy-5-methoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.52 g; 993 μmol), in acetonitrile (40 ml) is treated with trimethyl silyl iodide (0.353 ml; 2.483 mmol; 2.5 eq.) at 50° C. for 2 hours and then at 20° C. for 16 hours, in a 100 ml three-necked flask. After evaporation, the reaction mixture is taken up in a mixture of dichloromethane (50 ml) and water (50 ml) and is then separated by settling out. The aqueous phase is extracted with dichloromethane (250 ml); the extracts are combined, dried over magnesium sulfate, and evaporated to give a compound which is purified by chromatography on silica gel (10 g, 35 μm silica), elution being carried out with a mixture of cyclohexane and ethyl acetate (60/40 vol/vol). The fractions containing the expected compound are combined and evaporated, resulting in a solid which is triturated in diisopropyl ether so as to obtain 5-methoxy-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-6-ol, (0.215 g; 50%), the characteristics of which are as follows:

Workup

  1. customAfter evaporation
  2. additionthe reaction mixture is taken up in a mixture of dichloromethane (50 ml) and water (50 ml)
  3. customis then separated
  4. extractionThe aqueous phase is extracted with dichloromethane (250 ml)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customto give a compound which
  8. customis purified by chromatography on silica gel (10 g, 35 μm silica), elution
  9. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (60/40 vol/vol)
  10. additionThe fractions containing the expected compound
  11. customevaporated
  12. customresulting in a solid which
  13. customis triturated in diisopropyl ether so as

Sources & evidence

ORD record
ord-75a764ab68884c098780085a4f8b755b
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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