Sodium Carbonate → 1,3-Bis(1,1-dimethylethyl) 2-(4'-cyano-5,2'-dimethyl[1,1'-biphenyl]-3-yl)propanedioate

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,3-bis(1,1-dimethylethyl) 2-(3-iodo-5-methylphenyl)propanedioate (the product of Step A, 320 mg, 0.74 mmol), 4-cyano-2-methylphenylboronic acid (178 mg, 1.11 mmol), sodium carbonate (78 mg, 0.74 mmol), bis(triphenylphosphine)palladium(II) dichloride (52 mg, 0.074 mmol), dioxane (5 mL), and water (1 mL) was heated to 80° C. and stirred for 20 minutes. The reaction mixture was then cooled to room temperature, and filtered through a plug of silica gel eluting with 20% ethyl acetate in hexanes. Concentration of the eluant under reduced pressure provided a brown oil (430 mg) containing the crude product, which was used in the next step without further purification.

Provenance & Evidence