Reacción #595405

Ecuación de reacción

NaH

3,6-dibromocarbazole

N-(2-(oxiran-2-yl)ethyl)aniline

→

colorless oil

Rendimiento 57.5%

1-(3,6-dibromo-9H-carbazol-9-yl)-4-(phenylamino)butan-2-ol

Rendimiento 57.5%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe resulting mixture was stirred at 60° C. overnight
2. 2
   OtroTHF was removed under vacuum
3. 3
   workup.DISSOLUTIONthe residue was dissolved in 10 mL EtOAc
4. 4
   Lavadowashed with water 2×5 mL
5. 5
   SecadoThe organic layer was dried over anhydrous Na2SO4
6. 6
   Otroevaporated
7. 7
   Otroto afford the crude product, which

Procedimiento

NaH (60% dispersed in mineral oil, 0.0018 g, 0.0452 mmol) was added to a solution of 3,6-dibromocarbazole (0.0147 g, 0.0452 mmol) in 0.5 mL anhydrous THF and the mixture was stirred for 15 min. N-(2-(oxiran-2-yl)ethyl)aniline (0.0067 g, 0.0410 mmol) in 1.5 mL anhydrous THF solution was added dropwise and the resulting mixture was stirred at 60° C. overnight. THF was removed under vacuum and the residue was dissolved in 10 mL EtOAc and washed with water 2×5 mL. The organic layer was dried over anhydrous Na2SO4 and evaporated to afford the crude product, which was subjected to silica gel chromatography using Hexanes/EtOAc to afford 0.0115 g colorless oil; yield 57.5%.

Fuente