Water → HCID 123458513, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-[7-bromo-4-(2,4-difluorophenoxy)-1-methyl-1H-benzimidazol-5-yl]-6-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,6-dihydro-7H-pyrazolo[3,4-c]pyridin-7-one (0.0990 g, 0.160 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (0.0408 mL, 0.241 mmol), [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (0.0131 g, 0.0160 mmol) and potassium carbonate (0.0555 g, 0.401 mmol) in 1,4-dioxane (1.0 mL, 12.8 mmol) and water (0.580 mL, 32.2 mmol) was degassed with nitrogen for 10 min, warmed to 80° C. and stirred at 80° C. for 2 h. The reaction mixture was diluted with water and ethyl acetate. Layers were separated and the organic layer was washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo to give a crude residue. Purification by flash column chromatography (100% hexanes to 100% EtOAc [EtOAc contained 5% MeOH]) gave the desired product (77 mg, 85%) as a white foam. LCMS calculated for C29H32F2N5O3Si (M+H)+: m/z=564.2. found: 564.1.

Provenance & Evidence