Water → methyl (Z)-3-(3'-amino-2-butoxybiphenyl-4-yl)-2-methoxyacrylate

Participants

Reaction Conditions

Reaction Steps

11.2 mL (22.4 mmol) of aqueous 2 N potassium carbonate solution and 0.52 g (0.45 mmol) of tetrakis(triphenylphosphine)palladium are added to a solution of 1.87 g (10.8 mmol) of 3-aminophenylboronic acid hydrochloride and 3.5 g (9 mmol) of methyl (Z)-3-(3-butoxy-4-iodophenyl)-2-methoxyacrylate (prepared according to Example 24c) in 70 mL of ethylene glycol dimethyl ether. The reaction mixture is heated at 100° C. for 4 hours. After addition of 30 mL of water and extraction with ethyl acetate, the organic phases are combined, washed with saturated sodium chloride solution and dried over sodium sulfate. The solvents are evaporated off and the residue is then purified by chromatography on a column of silica eluted with a 90/10 heptane/ethyl acetate mixture. 3 g (93%) of methyl (Z)-3-(3′-amino-2-butoxybiphenyl-4-yl)-2-methoxyacrylate are obtained in the form of a yellow oil.

Provenance & Evidence