Sodium Chloride → 1-(2-fluoro-5-nitrophenyl)-3-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-6,7-dihydro-2H-pyrrolo[3,4-c]pyridin-4(5H)-one

Participants

Reaction Steps

2-fluoro-5-nitrophenylboronic acid (0.134 g, 0.725 mmol), tris(dibenzylidineacetone)dipalladium(0) (0.0157 g, 0.017 mmol), 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane (0.0165 g, 0.056 mmol) and tris-potassium phosphate (0.280 g, 1.319 mmol) were combined in a sealed 5 mL microwave tube with stir bar and sparged with nitrogen for 15 minutes. A solution of Example 93g (0.173 g, 0.481 mmol) in a degassed mixture of 4:1 dioxane/water (5.0 mL) was added by syringe into the reaction vessel which was heated at 110° C. for 25 minutes in a Biotage Initiator 2 monomode microwave reactor, then cooled to ambient temperature. The reaction mixture was shaken in a separatory funnel with 75 mL ethyl acetate and 40 mL saturated aqueous sodium chloride. The organics were dried over anhydrous sodium sulfate. Filtration and solvent removal gave a yellow oil which was chromatographed on a 40 g silica gel cartridge eluting with 0-100% ethyl acetate/heptane to provide the title compound.

Provenance & Evidence