반응 #592797

반응 방정식

ethyl acetate

methyl 4-{[{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

용매

dimethoxyethane

반응 조건

후처리

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

실험 절차

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.

출처