Reacción #84239

Ecuación de reacción

4-Fluoro-phenyl thiol

NaH

5-chloro-1-methanesulfonyl-2-(2-methyl-oxiranyl)-6-trifluoromethyl-1H-indole

→

title compound

2-(5-Chloro-6-trifluoromethyl-1H-indol-2-yl)-1-(4-fluoro-phenylsulfanyl)-propan-2-ol

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added into the reaction via syringe
2. 2
   OtroTHF was removed
3. 3
   Otrothe residue was partitioned between CH2Cl2 and water
4. 4
   LavadoThe organic layer was washed with brine
5. 5
   Secadodried over anhydrous Na2SO4
6. 6
   Concentraciónconcentrated
7. 7
   Otroto yield a crude white solid
8. 8
   OtroThe crude material was purified

Procedimiento

4-Fluoro-phenyl thiol (55 mg, 0.425 mmoL) was treated with NaH (60%, 17 mg, 0.425 mmoL) in THF (2 mL) at 0° C. After 10 min., 5-chloro-1-methanesulfonyl-2-(2-methyl-oxiranyl)-6-trifluoromethyl-1H-indole, the epoxide derivative compound prepared as in Example 72 (100 mg, 0.425 mmoL) in THF (1 mL) was added into the reaction via syringe. The reaction was slowly warmed to room temperature. THF was removed and the residue was partitioned between CH2Cl2 and water. The organic layer was washed with brine and dried over anhydrous Na2SO4, then concentrated to yield a crude white solid. The crude material was purified using column chromatography (silica gel, 3:1 hexanes:EtOAc as eluent) to yield the title compound as a white solid.

Fuente