Réaction #595301

Équation de réaction

2-(bromomethyl)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane

sodium hydride

2-iodoimidazole

→

1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2-iodo-1H-imidazole

Rendement 72.0%

Solvants

DMF

DMF

water

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe resulting mixture was stirred at 50° C. for 20 h
2. 2
   workup.WAITat 80° C. for 3 h
3. 3
   TempératureAfter cooling to room temperature
4. 4
   Extractionextracted with AcOEt
5. 5
   Autrethe extracts were dried
6. 6
   Concentrationconcentrated to dryness under reduced pressure
7. 7
   Concentrationconcentrated to dryness under reduced pressure
8. 8
   AutrePurification of the residue on silica gel

Mode opératoire

At 3° C., sodium hydride (60% by weight strength dispersion in mineral oil, 56.7 mg, 1.41 mmol) was added to a stirred solution of 2-iodoimidazole (242 mg, 1.25 mmol) in dry DMF (8 ml). The reaction mixture was stirred at room temperature for 20 min, and 2-(bromomethyl)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane (300 mg, 0.83 mmol) in dry DMF (4 ml) was then added. The resulting mixture was stirred at 50° C. for 20 h and then at 80° C. for 3 h. After cooling to room temperature, the reaction mixture was diluted with water and extracted with AcOEt, and the extracts were dried and concentrated to dryness under reduced pressure. The filtrates were combined and concentrated to dryness under reduced pressure. Purification of the residue on silica gel gave 1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2-iodo-1H-imidazole as a 55/45 mixture of diastereoisomers [298 mg, colourless solid, yield 72%; HPLC/MS: m/z=473 (M+H); log P(HCOOH)=2.92 (major diastereoisomer), 3.31 (minor diastereoisomer)].

Source