Potassium Phosphate, Tribasic → ethyl (Z)-2-ethoxy-3-[2-(2-ethoxyethoxy)-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]acrylate

Participants

Reaction Conditions

Reaction Steps

29 mg (0.08 mmol) of 2-(dicyclohexylphosphino)biphenyl and 9.3 mg (0.04 mmol) of palladium acetate and then 1.35 mL (2.7 mmol) of aqueous 2 M potassium phosphate solution are added to a solution of 0.9 g (2.07 mmol) of ethyl (Z)-3-[3-(2-ethoxyethoxy)-4-iodophenyl]-2-ethoxyacrylate and 0.58 g (2.5 mmol) of 3-(1-methyl-3-pentylureido)phenylboronic acid (prepared according to Example 24h) in 10 mL of dimethylformamide. The reaction medium 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. After evaporating under vacuum, the residue obtained is purified by chromatography on a column of silica eluted with an 80/20 heptane/ethyl acetate mixture. 100 mg (12%) of ethyl (Z)-2-ethoxy-3-[2-(2-ethoxyethoxy)-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]acrylate are obtained.

Provenance & Evidence