Trimethylsilyl iodide → HCID 22477326, compound

HRID 490469Notes

Reaction equation

HRID 490469 reaction equation
C([O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([C:19]3[N:27]([S:28]([C:31]4[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=4)(=[O:30])=[O:29])[C:22]4=[N:23][CH:24]=[CH:25][CH:26]=[C:21]4[CH:20]=3)=[CH:14][N:15]2[CH3:18])=[CH:11][C:10]=1[O:38][CH3:39])C1C=CC=CC=1.C[Si](I)(C)C>C(#N)C>[CH3:39][O:38][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:9]=1[OH:8])[N:15]([CH3:18])[CH:14]=[C:13]2[C:19]1[N:27]([S:28]([C:31]2[CH:32]=[CH:33][C:34]([CH3:37])=[CH:35][CH:36]=2)(=[O:30])=[O:29])[C:22]2=[N:23][CH:24]=[CH:25][CH:26]=[C:21]2[CH:20]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 22477636HCID 22477636, compound

Product 1

HCID 22477326HCID 22477326, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-(6-benzyloxy-5-methoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.5 g; 2.79 mmol) in acetonitrile (120 ml) is placed in a 250 ml three-necked flask at 20° C., and then trimethylsilyl iodide (0.956 ml; 6.97 mmol) is added dropwise. The reaction mixture is heated at 50° C. for 4 hours and is then evaporated to dryness under reduced pressure. The evaporation residue is taken up in dichloromethane (200 ml) and then washed with distilled water (1×200 ml). The extracts are combined, washed with distilled water, dried over magnesium sulfate and evaporated under reduced pressure, to produce the crude compound which is purified by chromatography on a silica cartridge (AIT FlashSmart Pack, BP-0610300-093, 50 g silica), elution being carried out at 15 ml/min with a dichloromethane/ethyl acetate (95/5 v/v) mixture. The fractions containing the expected product are combined and evaporated to give 5-methoxy-1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-6-ol (0.87 g; 70%) in the form of an ochre foam, which is used as it is for the following step.

Workup

  1. customis then evaporated to dryness under reduced pressure
  2. washwashed with distilled water (1×200 ml)
  3. washwashed with distilled water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customto produce the crude compound which
  7. customis purified by chromatography on a silica cartridge (AIT FlashSmart Pack, BP-0610300-093, 50 g silica), elution
  8. additionThe fractions containing the expected product
  9. customevaporated

Sources & evidence

ORD record
ord-e23d8bf542384cd5bbb5c7af4b1ef754
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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