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

Participants

Reaction Steps

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.

Provenance & Evidence