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 881678Notes

Reaction equation

HRID 881678 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 (65 g, 0.154 mol) in THF (880 mL) and saturated aqueous NH4Cl (220 mL). After 3 h, the reaction mixture was filtered and concentrated in vacuo. The residue was partitioned between EtOAc and H2O 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 washed with EtOAc (2×500 mL) and the combined organic layers were washed with H2O, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with CH2Cl2:EtOAc—90:10, to give the title compound. MS: m/z=265 (M+1).

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between EtOAc and H2O 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. washThe aqueous layer was washed with EtOAc (2×500 mL)
  8. washthe combined organic layers were washed with H2O
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe crude product was purified by silica gel chromatography
  13. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-83e7026ba47b4d2a99930c86647cd301
Source dataset
uspto-grants-2015_03
Patent number
US08993588B2

Reaction notes

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