1,4-Dioxane → HCID 66621877, compound

Participants

Reaction Steps

Combine 3-(4-bromo-2-(trifluoromethoxy)benzyl)-1-cyclohexylpyrrolidin-2-one (9.68 g, 23.0 mmol), 4-(methoxycarbonyl)phenylboronic acid (8.29 g, 46.1 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) (2.87 g, 3.9 mmol), dioxane (400 mL) and DMSO (8 mL) in a 1 L flask equipped with a magnetic stir bar, reflux condenser, and N2 inlet. Add potassium acetate (9.04 g, 92.1 mmol) and heat to 80° C. while stirring for 2 hours. Cool to room temperature, filter through silica gel and rinse with ethyl acetate (400 mL). Wash with water (2×400 mL) and saturated sodium chloride solution (1×400 mL), then dry over anhydrous magnesium sulfate and concentrate to an oil. Purify the crude product via silica gel chromatography eluting with 10% to 20% ethyl acetate in hexanes to afford 9.86 g (90%) of the product as a white solid. MS (m/z): 476 (M+1).

Provenance & Evidence