تفاعل #47177

معادلة التفاعل

(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

المذيبات

NMP

triethylamine

DME

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONThe reaction was worked up by addition
2. 2
   أخرىto crushed ice
3. 3
   استخلاصextracted with ethyl acetate (3×75 mL)
4. 4
   تجفيفthe organic layer was dried (MgSO4)
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated
7. 7
   أخرىThe crude product was chromatographed on silica gel using 10-30% EtOAc/Hexane

الإجراء التجريبي

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).

المصدر