Water → 1H-Pyrrolo[2,3-B]pyridine, 1-[(1,1-dimethylethyl)dimethylsilyl]-3-iodo-

HRID 1964951Notes

Reaction equation

HRID 1964951 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[H-].[Na+].[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].O>O1CCCC1>[C:16]([Si:13]([CH3:15])([CH3:14])[N:4]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:10]2[C:2]([I:1])=[CH:3]1)([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 53770783-Iodo-7-azaindole

Product 1

HCID 497589601H-Pyrrolo[2,3-B]pyridine, 1-[(1,1-dimethylethyl)dimethylsilyl]-3-iodo-Yield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Iodo-1H-pyrrolo[2,3-b]pyridine 634 (1.11 g, 4.6 mmol) was dissolved in tetrahydrofuran (120 mL). Sodium hydride (60% dispersion in mineral oil, 0.13 g, 5.5 mmol) was added, followed by tert-butyldimethylsilyl chloride (0.85 g, 5.5 mmol). The reaction was stirred at room temperature overnight. The reaction was poured into water and extracted with ethyl acetate. The organic portion was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified with silica gel column chromatography eluting with 30% ethyl acetate in hexane to give the compound as a white solid (636, 100 mg, 15%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic portion was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified with silica gel column chromatography
  7. washeluting with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-6ee670491745484c9eb799a6f0804e8b
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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