Reacción #595402

ord-709cc3ad8f374d4f87ac858cab4aa504

Ecuación de reacción

O=[N+]([O-])c1ccccc1S(=O)(=O)N(CCCn1c2ccc(Br)cc2c2cc(Br)ccc21)c1ccccc1
N-(3-(3,6-dibromo-9H-carbazol-9-yl)propyl)-2-nitro-N-phenylbenzenesulfonamide
O=C([O-])[O-].[Cs+].[Cs+]
cesium carbonate
Sc1ccccc1
benzenethiol
Brc1ccc2c(c1)c1cc(Br)ccc1n2CCCNc1ccccc1
colorless oil
Rendimiento 60.9%
Brc1ccc2c(c1)c1cc(Br)ccc1n2CCCNc1ccccc1
N-(3-(3,6-dibromo-9H-carbazol-9-yl) propyl)aniline
Rendimiento 60.9%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroTHF was removed under vacuum
  2. 2
    Otrothe residue was purified by silica gel chromatography

Procedimiento

N-(3-(3,6-dibromo-9H-carbazol-9-yl)propyl)-2-nitro-N-phenylbenzenesulfonamide (0.0378 g, 0.0588 mmol, 1 equiv), cesium carbonate (0.0574 g, 0.176 mmol, 3 equiv) and benzenethiol (0.0194 g, 0.176 mmol) were mixed in 1 mL anhydrous THF. The mixture was stirred at room temperature for 3 hours. THF was removed under vacuum and the residue was purified by silica gel chromatography using Hexanes/EtOAc to afford 0.0164 g colorless oil as product, yield 60.9%.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09095572B2uspto-grants-2015_08