Ammonium Chloride → ethyl (E)-3-[2-butoxy-3'-(1-methyl-3-heptylureido)biphenyl-4-yl]-2-methylacrylate

Participants

Reaction Conditions

Reaction Steps

In a manner similar to that of Example 34a, 3 mg (0.013 mmol) of palladium acetate and then 9 mg (0.026 mmol) of 2-(dicyclohexylphosphino)biphenyl are added to a mixture of 505 mg (1.3 mmol) of ethyl (E)-3-(3-butoxy-4-iodophenyl)-2-methylacrylate prepared as described in Example 19h, 494 mg (1.7 mmol) of 3-heptyl-1-methyl-1-[3-(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)phenyl]urea and 1.3 mL of aqueous 2 M potassium phosphate solution in 6.5 mL of dimethylformamide. The reaction mixture is heated at 90-95° C. for 2 hours. The reaction medium is hydrolyzed with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution and dried over magnesium sulfate. The solvent is evaporated off and the brown oil obtained (1.3 g) is purified by chromatography on a column of silica eluted with a 70/30 heptane/ethyl acetate mixture. 558 mg (84%) of ethyl (E)-3-[2-butoxy-3′-(3-heptyl-1-methyl-ureido)biphenyl-4-yl]-2-methylacrylate are obtained.

Provenance & Evidence