N-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → methyl(E)-3-(2-butoxy-3'-methylaminobiphenyl-4-yl)acrylate

Participants

Reaction Steps

In a manner similar to that of Example (18d), by reaction of 28 mg (1 mol %) of palladium acetate, 88 mg (2 mol %) of dicyclohexylbiphenylphosphine, 4.5 g (12.5 mmol, 1.0 eq) of methyl (E)-3-(3-butoxy-4-iodophenyl)acrylate and 3.79 g (16.2 mmol, 1.3 eq) of methyl[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]amine (prepared in Example 7a) in 72 mL of a mixture of dimethylformamide/2M potassium phosphate solution (5/1) at 90° C. for 2 hours, 3.67 g of methyl (E)-3-(2-butoxy-3′-methylaminobiphenyl-4-yl)acrylate are obtained in the form of crystals. Yield=86%

Provenance & Evidence