Sodium hydride → 5-Bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

HRID 2108737Notes

Reaction equation

HRID 2108737 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[N:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.[CH:13]([Si:16](Cl)([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])([CH3:15])[CH3:14]>C1COCC1>[Br:3][C:4]1[CH:5]=[C:6]2[CH:7]=[CH:8][N:9]([Si:16]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:13]([CH3:15])[CH3:14])[C:10]2=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 242292235-Bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridineYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.63 g, 25.15 mol) was added in small portion to a stirred solution of 5-bromo-7-azaindole (3.3 g, 16.75 mmol) in THF (50 mL) at room temperature and the resulting suspension was stirred at room temperature for 15 min. Triisopropylsilyl chloride (5.3 mL, 25.15 mmol) was added and the mixture was heated at 80° C. for 3 h. The solvent was evaporated and the residue was dissolved in water (50 mL). The aqueous layer was extracted with EtOAc (3×50 mL), dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by Biotage HPFC system (10% EtOAc/Hexane) to afford the desired 5-bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine as a white solid (5.2 g, 88%); Mass Spec 355 (M+1).

Workup

  1. temperaturethe mixture was heated at 80° C. for 3 h
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in water (50 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (3×50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by Biotage HPFC system (10% EtOAc/Hexane)

Sources & evidence

ORD record
ord-4cab729eb25742e5beefd8c14c7a81a4
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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