تفاعل #58883

معادلة التفاعل

pent-4-yn-1-ol

2-amino-5-(3-bromophenyl)-5-[4-(difluoromethoxy)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one

tri-tert-butyl phosphine

diisopropyl amine

→

title compound

المردود 73.3%

2-Amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(5-hydroxypent-1-yn-1-yl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one

المردود 73.3%

المذيبات

water

dioxane

ظروف التفاعل

المعالجة

1. 1
   أخرىwas degassed under argon for 5 minutes
2. 2
   استخلاصextracted with ethyl acetate
3. 3
   تجفيفdried over MgSO4
4. 4
   تركيزconcentrated in vacuo
5. 5
   أخرىPurification of the resultant residue by ICSO (EtOAc/MeOH 10/1)

الإجراء التجريبي

A mixture of 2-amino-5-(3-bromophenyl)-5-[4-(difluoromethoxy)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one (1.15 g, 2.8 mmol), dioxane, bis(benzonitrile)dichloropalladium(II) (32.2 mg, 0.084 mmol), tri-tert-butyl phosphine (10% w/w in hexane, 339 mg, 0.17 mmol) and diisopropyl amine (340 mg, 3.36 mmol) was degassed under argon for 5 minutes, treated with pent-4-yn-1-ol (236 mg, 2.8 mmol), stirred at 80° C. for 5 hours, poured into water and extracted with ethyl acetate. The organic extracts were combined, dried over MgSO4 and concentrated in vacuo. Purification of the resultant residue by ICSO (EtOAc/MeOH 10/1) gave the title compound as a white solid (849 mg), identified by NMR and mass spectral analyses. MS m/e [M+H]+ 414.2

المصدر