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 2262818Notes

Reaction equation

HRID 2262818 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.[Cl-].[NH4+].[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 ammonium chloride (220 mL). After 3 h, the reaction 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×) and the combined organic layers were washed with H2O, dried over MgSO4, filtered, and concentrated. The crude product was filtered through 5a plug of silica gel eluting with EtOAc:CH2Cl2—1:9 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 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×)
  8. washthe combined organic layers were washed with H2O
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. filtrationThe crude product was filtered through 5a plug of silica gel eluting with EtOAc
  13. concentrationCH2Cl2—1:9 and the eluant was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9f24616486ed478dae1ca6d69ec34a1f
Source dataset
uspto-grants-2010_12
Patent number
US07851464B2

Reaction notes

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