Potassium Carbonate → Methyl 2-(1,2-dimethyl-1-propenyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 66.15D (0.231 g, 0.60 mmol) in DMF (4.00 mL) at 23° C. was added 3-methylbut-2-en-2-ylboronic acid (0.14 g, 1.2 mmol, commercially available from Aldrich), and potassium carbonate (0.25 g, 1.8 mmol). Tetrakis(triphenylphosphine)palladium (0.069 g, 0.060 mmol) was then added to the reaction. The mixture was heated to 90° C. and stirring was continued for 18 hours. The reaction was then cooled to room temperature, diluted with water and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-10% EtOAc in hexanes) to yield 69.12A as a colorless oil (0.100 g, 51% yield).

Provenance & Evidence