Water → methyl (Z)-2-Ethoxy-3-[2-(2-ethoxyethoxy)-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]acrylate

Participants

Reaction Conditions

Reaction Steps

6.9 mg (0.02 mmol) of 2-(dicyclohexylphosphino)biphenyl and 2.2 mg (0.01 mmol) of palladium acetate and then 0.32 mL (0.64 mmol) of aqueous 2 M potassium phosphate solution are added to a solution of 200 mg (0.49 mmol) of methyl (Z)-3-[3-(2-ethoxyethoxy)-4-iodophenyl]-2-methoxyacrylate and 0.65 g (2.5 mmol) of 3-(1-methyl-3-pentylureido)phenylboronic acid (prepared according to Example 24h) in 10 mL of dimethylformamide. The reaction mixture is heated at 90° C. for 3 hours. After addition of 20 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 70/30 heptane/ethyl acetate mixture. 217.8 mg (89%) of methyl (Z)-2-Ethoxy-3-[2-(2-ethoxyethoxy)-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]acrylate are obtained in the form of an orange oil.

Provenance & Evidence