Reacción #58865

Ecuación de reacción

K2CO3

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

1,3-bis(diphenylphosphino)propane

K2CO3

n-butylvinylether

HCl

→

title compound

Rendimiento 88.0%

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

Rendimiento 88.0%

Disolventes

water

DMF water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to room temperature
2. 2
   Extracciónextracted with ethyl acetate
3. 3
   Secadodried over MgSO4
4. 4
   Concentraciónconcentrated in vacuo
5. 5
   Otroto give a residue
6. 6
   OtroThe residue is purified by SCX cartridge

Procedimiento

A mixture of 2-amino-5-(3-bromophenyl)-5-[4-(difluoromethoxy)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one (1.50 g, 3.66mmol), 1,3-bis(diphenylphosphino)propane (DPPP) (0.377 g, 0.915 mmol), K2CO3 (0.606 g, 4.39 mmol), Pd(OAc)2 (82 mg, 0.37 mmol) and n-butylvinylether (1.47 g, 14.6 mmol) in DMF/water (8 ml/0.8 ml) is heated in a microwave oven for 1 h at 120° C., cooled to room temperature, treated cautiously with 15 ml of 5% HCl, stirred at room temperature for 1 h, diluted with water, basified with aqueous K2CO3 and extracted with ethyl acetate. The extracts are combined, dried over MgSO4 and concentrated in vacuo to give a residue. The residue is purified by SCX cartridge to give the title compound, 1.20 g (88% yield), identified by NMR and mass spectral analyses. 1H NMR (300 MHz,CDCl3) ppm 8.11 (t, 1 H), 7.87 (dt, 1 H), 7.72-7.80 (m, 1 H), 7.52 (d, 2 H), 7.44 (t, 1 H), 7.08 (d, 2 H), 6.49 (t, 1 H), 3.15 (s, 3 H), 2.59 (s, 3 H). MS [M+H]+ 374.1.

Fuente