Potassium Phosphate, Tribasic → HCID 16224622, compound

Participants

Reaction Conditions

Reaction Steps

870 g (2.2 mmol) of (Z)-3-(3-butoxy-4-(trifluoromethanesulphonyloxy)phenyl)-2-methoxyacrylic acid (XII), 981 mg (2.62 mmol) of 3-heptyl-1-methyl-1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea (III) [prepared according to International Application WO2007/049158], 14 mg (3 mol %) of palladium acetate and 46 mg (6 mol %) of dicyclohexylbiphenylphosphine are dissolved in 8 ml of dimethylformamide, 1.5 ml of a 2M potassium phosphate solution are added and the medium is degassed several times. The reaction mixture is stirred at 90° C. for 2 hours. The reaction is halted with a 2M hydrochloric acid solution and then the mixture is extracted with ethyl acetate. The organic phases are washed with a sodium chloride solution and then dried over Na2SO4. The solvents are evaporated and then the residue is taken up in 10 ml of heptane/AcOEt 1/1. Filtration is carried out through a silica patch (1 cm). The solvents are evaporated. The residue is precipitated from pentane. The solid is recrystallized from isopropyl ether/heptane. 510 mg of (Z)-3-[2-butoxy-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]-2-methoxyacrylic acid are obtained in the solid form.

Provenance & Evidence