Reaktion #477849

Reaktionsgleichung

ammonium chloride

ethyl 2-[1-(3-butoxy-4-iodophenyl)meth-(E)-ylidene]butyrate

3-heptyl-1-methyl-1-[3-(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)phenyl]urea

potassium phosphate

→

ethyl 2-[1-[2-butoxy-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]meth-(E)-ylidene]butyrate

Ausbeute 79.0%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   Waschenwashed with saturated sodium chloride solution
3. 3
   Trocknendried over magnesium sulfate
4. 4
   FiltrationAfter filtration
5. 5
   Sonstigethe solvent is evaporated off
6. 6
   Sonstigethe brown oil obtained (1.3 g)
7. 7
   Sonstigeis purified by chromatography on a column of silica
8. 8
   Wascheneluted with a 70/30 heptane/ethyl acetate mixture

Vorschrift

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 523 mg (1.3 mmol) of ethyl 2-[1-(3-butoxy-4-iodophenyl)meth-(E)-ylidene]butyrate (prepared as described in Example 22a), 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 (prepared according to Example 35b) and 1.3 mL of aqueous 2M 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 ammonium chloride solution and extracted with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution and dried over magnesium sulfate. After filtration, 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. 537 mg (79%) of ethyl 2-[1-[2-butoxy-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]meth-(E)-ylidene]butyrate are obtained.

Quelle