Reacción #595393

Ecuación de reacción

2-Butanone

4-bromophenylhydrazine hydrochloride

→

indole

Rendimiento 67.0%

5-Bromo-2,3-dimethyl-1H-indole

Rendimiento 67.0%

Disolventes

EtOH

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was heated
2. 2
   Temperaturato reflux for 22 h
3. 3
   Concentraciónconcentrated in vacuo
4. 4
   Otropartitioned between EtOAc and 1N HCl
5. 5
   LavadoThe organic layer was washed with H2O and saturated aqueous NaHCO3
6. 6
   Secadodried over Na2SO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated
9. 9
   OtroThe crude residue was purified by chromatography (SiO2, 0-20% EtOAc/Hexane)

Procedimiento

Following a published procedure (Gundersen, E. G. U.S. Patent App. Publ. US 2005/070592) 2-Butanone (0.11 mL, 1.278 mmol) was added to a solution of 4-bromophenylhydrazine hydrochloride (0.300 g, 1.342 mmol in EtOH (3.8 mL). The mixture was heated to reflux for 22 h, concentrated in vacuo, and partitioned between EtOAc and 1N HCl. The organic layer was washed with H2O and saturated aqueous NaHCO3, dried over Na2SO4, filtered, and concentrated. The crude residue was purified by chromatography (SiO2, 0-20% EtOAc/Hexane) to afford the desired indole as a pink powder (200 mg, 67%).

Fuente