Sodium Carbonate → ethyl (Z)-2-ethoxy-3-(3'-methylaminobiphenyl-4-yl)acrylate

Participants

Reaction Steps

To a solution of 10.8 g (36.1 mmol) of ethyl (Z)-3-(4-bromophenyl)-2-ethoxyacrylate prepared beforehand as described in Example 1c and 108 mL (217 mmol) of aqueous 2 M sodium carbonate solution in 120 mL of toluene, 1.5 g (1.8 mmol) of dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium are added. The reaction medium is stirred and a solution of 9.25 g (39.7 mmol) of methyl[3-(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)phenyl]amine in 90 mL of ethanol is then added dropwise. After stirring at 80° C. for 2 hours, the reaction medium is hydrolyzed and diluted with ethyl acetate. After separation of the phases by settling, the ethyl acetate phase is washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a 90/10 and then 80/20 heptane/ethyl acetate mixture. 10.5 g (94%) of ethyl (Z)-2-ethoxy-3-(3′-methylaminobiphenyl-4-yl)acrylate are obtained in the form of a yellow oil. After taking up the product in pentane, 9.5 g (85%) of ethyl (Z)-2-ethoxy-3-(3′-methylaminobiphenyl-4-yl)acrylate are obtained in the form of a pale yellow solid with a melting point of 52° C.

Provenance & Evidence