Water → methyl (E)-3-[2-butoxy-3'-(1-methyl-3-heptylureido)biphenyl-4-yl]-2-methoxyacrylate

Participants

Reaction Conditions

Reaction Steps

0.4 g (1 mmol) of methyl (E)-3-(3-butoxy-4-iodophenyl)-2-methoxyacrylate prepared as described in Example 24c, 0.5 g (1.33 mmol) of 3-heptyl-1-methyl-1-[3-(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)phenyl]urea prepared according to Example 35b and 1 mL (2 mmol) of aqueous 2 M potassium phosphate solution are dissolved in 15 mL of dimethylformamide. After bubbling nitrogen through the reaction mixture for 10 minutes, 2 mg (0.01 mmol) of palladium (II) acetate and 7 mg (0.02 mmol) of 2-(dicyclohexylphosphine)biphenyl are added. The reaction mixture is heated at 90° C. for 3 hours with vigorous stirring. After cooling, the reaction is worked up by addition of water and extraction with ethyl acetate. The organic phases are combined, washed with water and with saturated sodium chloride solution and then dried over magnesium sulfate. The solvents are evaporated off. The crude product obtained is purified by chromatography on a column of silica eluted with a 70/30 heptane/ethyl acetate mixture to give 0.33 g (64%) of methyl (E)-3-[2-butoxy-3′-(1-methyl-3-heptylureido)biphenyl-4-yl]-2-methoxyacrylate in the form of a colorless oil.

Provenance & Evidence