Reacción #158838

Ecuación de reacción

EtOH

2-Bromo-N-[1-dimethylaminometh-(E)-ylidene]-benzenesulfonamide

4-methylphenylboronic acid

potassium carbonate

toluene

→

title compound

Rendimiento 82.7%

4′-Methylbiphenyl-2-sulfonic acid 1-dimethylaminometh-(E)-ylideneamide

Rendimiento 82.7%

Disolventes

water

EtOAc

Water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to room temperature
2. 2
   LavadoThe mixture was washed with saturated aqueous NaCl
3. 3
   Extracciónextracted with EtOAc
4. 4
   Secadodried over MgSO4
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   Otroto yield a red solid
8. 8
   OtroThe product was triturated with 1:1 EtOAc
9. 9
   Filtraciónhexanes, filtered
10. 10
    Lavadorinsed with hexanes
11. 11
    Otroto yield a reddish-brown solid
12. 12
    OtroThe product was triturated with EtOAc
13. 13
    Filtraciónfiltered
14. 14
    Lavadorinsing with EtOAc

Procedimiento

2-Bromo-N-[1-dimethylaminometh-(E)-ylidene]-benzenesulfonamide (5.4 g, 18.4 mmol), 4-methylphenylboronic acid (5.0 g, 36.8 mmol) and potassium carbonate (5.1 g, 36.8 mmol) were dissolved in water (19.7 mL, 1090 mmol), EtOH (49.2 mL, 842 mmol) and toluene (98.3 mL, 923 mmol). The resulting mixture was stirred under nitrogen. Tetrakis(triphenylphosphine)palladium(0) (1.4 g, 1.2 mmol) was added. The mixture was heated at 60° C. for 115 minutes, at 70° C. for 30 minutes, then cooled to room temperature. Water (100 mL) and EtOAc (100 mL) were added. The mixture was washed with saturated aqueous NaCl, extracted with EtOAc, dried over MgSO4, filtered, and concentrated to yield a red solid. The product was triturated with 1:1 EtOAc:hexanes, filtered, and rinsed with hexanes to yield a reddish-brown solid. The product was triturated with EtOAc, filtered, and rinsing with EtOAc to yield the title compound (4.6 g) as a light brown solid.

Fuente