Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl- → 2-Methyl-2-(6-nitropyridin-3-yl)-propionic acid methyl ester

Participants

Reaction Steps

5-Bromo-2-nitro-pyridine (7.0 g, 35 mmol), (1-methoxy-2-methyl-propenyloxy)-trimethyl-silane (12.0 g, 69 mmol), bis(dibenzylideneacetone)palladium (1.0 g, 1.75 mmol), and zinc fluoride (1.8 g, 17.5 mmol) were added to a round bottom flask and purged with nitrogen. Tri-tert-butylphosphine (3.5 ml of a 1.0 M solution in toluene) and 140 ml of DMF were added by syringe. The reaction mixture was heated at 80 degrees centigrade overnight. The reaction was diluted with ethyl acetate, water was added, and the layers were separated. The organic layer was washed with water and brine, dried and concentrated. The crude product was purified by flash chromatography using a gradient of 0% to 15% ethyl acetate in hexanes to yield 1.88 g (24%) of 2-methyl-2-(6-nitropyridin-3-yl)-propionic acid methyl ester.

Provenance & Evidence