Potassium Phosphate, Tribasic → methyl(E)-3-[3'-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]acrylate

Participants

Reaction Steps

A solution of 4.6 g (11.67 mmol, 1 eq) of methyl (E)-3-(3-benzyloxy-4-iodophenyl)acrylate, 4.8 g (12.83 mmol, 1.1 eq) of 3-heptyl-1-methyl-1-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]urea (prepared as in Example 1e) in 18 ml of dimethylformamide+3 mL of 2M potassium phosphate solution, in the presence of 128 mg (5 mol %) of palladium acetate and 408 mg (10 mol %) of 2-(dicyclohexylphosphino)biphenyl is stirred at 80° C. for 5 hours. The reaction medium is hydrolyzed in water and then extracted with ethyl acetate. The organic phases are washed with saturated sodium chloride solution and dried over sodium sulfate. The solvents are evaporated off and the oil obtained is chromatographed on silica (7/3 heptane/ethyl acetate). 5.89 g of methyl (E)-3-[3′-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]acrylate are obtained in oil form. Yield=98%

Provenance & Evidence