Potassium Carbonate → tert-butyl 2-(3-fluoro-5-methoxyphenyl)-4-((3-chloro-4-fluoro-N-methylphenylsulfonamido)methyl)phenoxyacetate

Participants

Reaction Conditions

Reaction Steps

To a mixture of tert-butyl 2-(2-bromo-4-((3-chloro-4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetate (10) (140 g, 0.27 mol, 1 eq), 3-fluoro-5-methoxyphenylboronic acid (45.7 g, 0.27 mol, 1 eq, Combi-Blocks Inc., San Diego, Calif., USA) and potassium carbonate (111 g, 0.81 mol, 3 eq) in dioxane/water (3:1, 800 mL) was added tetrakis(triphenylphoshine)palladium (3.08 g, 2.7 mmol, 0.01 eq). The mixture was heated at 60° C. for 3 h under N2. Solvent was evaporated, and the solid was dissolved in DCM and filtered. The DCM was evaporated and the crude product was recrystallized from ethanol to yield tert-butyl 2-(3-fluoro-5-methoxyphenyl)-4-((3-chloro-4-fluoro-N-methylphenylsulfonamido)methyl)phenoxyacetate (11) (70 g, 41%).

Provenance & Evidence