Reacción #2045098

Ecuación de reacción

furan-2-carboxamide

DIEA

2-bromo-1-(2,4-dichlorophenyl)ethanone

→

4-(2,4-Dichloro-phenyl)-2-furan-2-yl-oxazole

Rendimiento 55.0%

Disolventes

NMP

HCl

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroReaction mixture
2. 2
   TemperaturaThe mixture was cooled down
3. 3
   Extracciónextracted with EtOAc (40 mL)
4. 4
   LavadoThe organic layer was washed with 1 M HCl (30 mL), 5% solution of NaHCO3 (30 mL), brine (2×40 mL)
5. 5
   Secadodried over anhydrous Na2SO4
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroThe resulting residue was purified by HPLC purification

Procedimiento

To the solution of furan-2-carboxamide (56 mg, 0.5 mmol. 1 eq) and DIEA (0.13 mL, 0.75 mmo, 1.5 eq) in NMP (1 mL) was added 2-bromo-1-(2,4-dichlorophenyl)ethanone (0.6 mmol, 1.2 eq). Reaction mixture was heated at 130° C. for 15 h. The mixture was cooled down, diluted with 1 M HCl (30 mL) and extracted with EtOAc (40 mL). The organic layer was washed with 1 M HCl (30 mL), 5% solution of NaHCO3 (30 mL), brine (2×40 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. The resulting residue was purified by HPLC purification to provide desired 4-(2,4-Dichloro-phenyl)-2-furan-2-yl-oxazole in a yield of 55% and HPLC 99.9% purity. LC-MS [M+H]−280.4 (C13H7Cl2NO2+H, requires 281.11). 1H NMR (DMSO-d6) δ 8.84 (s, 1H), 8.13 (d, 1H, J=8.5), 8.01 (s, 1H), 7.78 (s, 1H), 7.58 (d, 1H, J=8.5), 7.29 (d, 1H, J=3.5), 6.77 (m, 1H).

Fuente