3,3-Dibromo-1,3-dihydro-1-((2-(trimethylsilyl)ethoxy)methyl)-2H-pyrrolo(2,3-b)pyridin-2-one → 1-{[2-(Trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

HRID 1675739Notes

Reaction equation

HRID 1675739 reaction equation
Br[C:2]1(Br)[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:3]1=[O:19]>C1COCC1.[NH4+].[Cl-].[Zn]>[CH3:16][Si:15]([CH3:18])([CH3:17])[CH2:14][CH2:13][O:12][CH2:11][N:4]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:10]2[CH2:2][C:3]1=[O:19]

Participants

5

Reactant 1

HCID 574588853,3-Dibromo-1,3-dihydro-1-((2-(trimethylsilyl)ethoxy)methyl)-2H-pyrrolo(2,3-b)pyridin-2-one

Product 1

HCID 574588861-{[2-(Trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Zinc (100 g, 1.54 mol) was added to a solution of 3,3-dibromo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one from Step B (65 g, 0.154 mol) in THF (880 mL) and saturated aqueous NH4Cl (220 mL). After 3 h, the reaction was filtered and concentrated in vacuo. The residue was partitioned between EtOAc (500 mL) and H2O (500 mL), which resulted in the formation of a white precipitate. Both layers were filtered through a Celite pad and the layers were separated. The aqueous layer was further extracted with EtOAc (2×200 mL) and the combined organic layers were washed with H2O (100 mL), dried over MgSO4, filtered, and concentrated. The crude product was filtered through a plug of silica gel, eluting with EtOAc:CH2Cl2-10:90, and the eluant was concentrated under reduced pressure to provide the title compound. MS: m/z=265 (M+1).

Workup

  1. filtrationthe reaction was filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between EtOAc (500 mL) and H2O (500 mL), which
  4. customresulted in the formation of a white precipitate
  5. filtrationBoth layers were filtered through a Celite pad
  6. customthe layers were separated
  7. extractionThe aqueous layer was further extracted with EtOAc (2×200 mL)
  8. washthe combined organic layers were washed with H2O (100 mL)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. filtrationThe crude product was filtered through a plug of silica gel
  13. washeluting with EtOAc
  14. concentrationCH2Cl2-10:90, and the eluant was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e81a1c0085a54e519b93105432f94a0e
Source dataset
uspto-grants-2011_08
Patent number
US08003792B2

Reaction notes

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