Sodium Carbonate → HCID 86723267, compound

Participants

Reaction Conditions

Reaction Steps

To 2-bromo-5-(ethylsulfonyl)benzonitrile (Preparation 75, 1.09 g, 3.96 mmol) in dioxane/water (5:1 v/v, 66 mL) was added 2-(2-fluoro-5-((4-methoxybenzyl)oxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 71, 1.56 g, 4.35 mmol) and sodium carbonate (1.26 g, 11.9 mmol). The reaction mixture was degassed and tetrakis(triphenylphosphine) palladium(0) (462 mg, 0.40 mmol) was added, and the reaction heated to 110° C. under nitrogen for 12 hours. After cooling to room temperature, silica gel was added, and the solvent removed under reduced pressure. The residue was purified using silica gel column chromatography eluting with EtOAc/cyclohexane 1:3 followed by reverse phase column chromatography eluting with MeCN/water, with 0.1% NH3 0-100% to afford the title compound as a solid in 51% yield, 851 mg.

Provenance & Evidence