تفاعل #8230

معادلة التفاعل

ethyl acetate

{[{2-[(4-bromobenzyl)oxy]phenethyl}(5-ethoxy-5-oxopentyl)amino]methyl}benzoate

4-chlorophenylboronic acid

sodium carbonate

→

Methyl 4-{[{2-[(4′-chloro[1,1′-biphenyl]-4-yl)methoxy]phenethyl}(5-ethoxy-5-oxopentyl)amino]methyl}benzoate

المذيبات

dimethoxyethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture is then heated
2. 2
   درجة الحرارةat reflux temperature for 18 hours
3. 3
   درجة الحرارةThe reaction solution is cooled
4. 4
   غسيلwashed successively with 5% strength sodium hydrogen phosphate solution, water and saturated sodium chloride solution
5. 5
   تجفيفThe organic phase is dried over magnesium sulphate
6. 6
   workup.DISTILLATIONthe solvent is distilled off under reduced pressure
7. 7
   أخرىThe crude product is chromatographed over silica gel using the mobile phase cyclohexane/ethyl acetate=10:1

الإجراء التجريبي

300.0 mg (0.51 mmol) of methyl 4-({[{2-[(4-bromobenzyl)oxy]phenethyl}(5-ethoxy-5-oxopentyl)amino]methyl}benzoate from Ex. 4 are initially charged in 3 ml of dimethoxyethane and admixed successively with 101.7 mg (0.62 mmol) of 4-chlorophenylboronic acid and 0.57 ml of 2M sodium carbonate solution. 10.0 mg of dichlorobis(triphenylphosphine)palladium(II) are added, and the mixture is then heated at reflux temperature for 18 hours. The reaction solution is cooled, admixed with 20 ml of ethyl acetate and washed successively with 5% strength sodium hydrogen phosphate solution, water and saturated sodium chloride solution. The organic phase is dried over magnesium sulphate and the solvent is distilled off under reduced pressure. The crude product is chromatographed over silica gel using the mobile phase cyclohexane/ethyl acetate=10:1.

المصدر