2H-Pyrrolo[2,3-b]pyridin-2-one, 3,3,5-tribromo-1,3-dihydro-1-[[2-(trimethylsilyl)ethoxy]methyl]- → 5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-one

HRID 712553Notes

Reaction equation

HRID 712553 reaction equation
Br[C:2]1(Br)[C:10]2[C:5](=[N:6][CH:7]=[C:8]([Br:11])[CH:9]=2)[N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:3]1=[O:20]>CC(O)=O.[Zn]>[Br:11][C:8]1[CH:9]=[C:10]2[CH2:2][C:3](=[O:20])[N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 667794342H-Pyrrolo[2,3-b]pyridin-2-one, 3,3,5-tribromo-1,3-dihydro-1-[[2-(trimethylsilyl)ethoxy]methyl]-

Product 1

HCID 667795225-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-oneYield 25%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 3,3,5-tribromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (4.98 g, 10.0 mmol) in AcOH (50 mL) was added zinc dust (1.28 g, 20.0 mmol). The resulting mixture was stirred at room temperature for 2 hr, after which it was filtered thru Celite and concentrated in vacuo. The resulting residue was purified via silica gel chromatography eluting with 1:1 Hexanes:EtOAc to yield the title compound as a yellow oil (0.85 g, 25% over three steps). HPLC retention time: 2.60 minutes; MS ESI (m/z): 287.2 (Fragment+1)+, calc. 342.

Workup

  1. filtrationafter which it was filtered thru Celite
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was purified via silica gel chromatography
  4. washeluting with 1:1 Hexanes

Sources & evidence

ORD record
ord-09bc86c6b19f4bf589d380d8b9646870
Source dataset
uspto-grants-2015_11
Patent number
US09181247B2

Reaction notes

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