Reacción #47177

Ecuación de reacción

(4-methoxyphenyl)boronic acid

N-(2-Benzoyl-4-chloro-phenyl)-4-iodo-benzenesulfonamide

dichloromethane

cesium carbonate

→

4′-Methoxy-biphenyl-4-sulfonic acid (2-benzoyl-4-chloro-phenyl)-amide

Disolventes

NMP

triethylamine

DME

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONThe reaction was worked up by addition
2. 2
   Otroto crushed ice
3. 3
   Extracciónextracted with ethyl acetate (3×75 mL)
4. 4
   Secadothe organic layer was dried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe crude product was chromatographed on silica gel using 10-30% EtOAc/Hexane

Procedimiento

To a magnetically stirred mixture of N-(2-Benzoyl-4-chloro-phenyl)-4-iodo-benzenesulfonamide (497 mg, 1.0 mmol), [1,1′ Bis(diphenylphosphino)-ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (30 mg, 0.037 mmol) and dry cesium carbonate (511 mg, 1.57 mmol) in NMP (3 mL), was added DME (3 mL) and dry triethylamine (3 mL) under dry nitrogen. To this stirred mixture was added (4-methoxyphenyl)boronic acid (202 mg) and the mixture was stirred at 55° C. overnight. The reaction was worked up by addition to crushed ice and extracted with ethyl acetate (3×75 mL), and the organic layer was dried (MgSO4), filtered and concentrated. The crude product was chromatographed on silica gel using 10-30% EtOAc/Hexane. 1H NMR (CDCl3) 89.64 (brs, 1H, NH), 7.75 (dm, 1H), 7.75 (dm, 2H, J=8.8 Hz), 7.48 (m, 3H), 7.56 (dm, 2H, J=8.4 Hz), 7.51 (m), 7.32 (d 1H, J=2.2 Hz), 7.26 (d, 1H, J=7 Hz), 7.09 (d, 2H, J=8.4 Hz), 3.65 (s, 3H). MS: m/z 478.0 (M+1).

Fuente