تفاعل #45550

معادلة التفاعل

N-(3-Bromo-6-cyano-4-iodo-2-methoxy-5-methylphenyl)-2,2-dimethylpropionamide

3-nitrophenylboronic acid

tripotassium phosphate

→

compound

المردود 68.0%

N-(2-Bromo-5-cyano-3-methoxy-6-methyl-3′-nitrobiphenyl-4-yl)-2,2-dimethylpropionamide

المردود 68.0%

المذيبات

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   أخرىby purging with nitrogen
2. 2
   أخرىN,N-Dimethylformamide (20 ml) was injected into it with a syringe
3. 3
   درجة الحرارةAfter cooling
4. 4
   أخرىthe reaction liquid
5. 5
   غسيلsuccessively washed with saturated brine (×3), 1 N hydrochloric acid, saturated brine
6. 6
   تجفيفan aqueous saturated sodium hydrogencarbonate solution and saturated brine, dried on anhydrous magnesium sulfate
7. 7
   تركيزthe solvent was concentrated under reduced pressure
8. 8
   أخرىto obtain a pale brown residue
9. 9
   أخرىThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1→4:1)

الإجراء التجريبي

N-(3-Bromo-6-cyano-4-iodo-2-methoxy-5-methylphenyl)-2,2-dimethylpropionamide (I-6) (965 mg, 2.14 mmol), 3-nitrophenylboronic acid (375 mg, 2.25 mmol), tripotassium phosphate (74-85%, 1.23 g, 4.28 mmol) and tetrakis(triphenylphosphine)palladium(0) (247 mg, 0.214 mmol) were added to a 50-ml eggplant-type flask, followed by purging with nitrogen. N,N-Dimethylformamide (20 ml) was injected into it with a syringe, followed by stirring at 95° C. for 4 hours. After cooling, the reaction liquid was diluted with ethyl acetate, successively washed with saturated brine (×3), 1 N hydrochloric acid, saturated brine, an aqueous saturated sodium hydrogencarbonate solution and saturated brine, dried on anhydrous magnesium sulfate, then the solvent was concentrated under reduced pressure to obtain a pale brown residue. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1→4:1) to obtain the entitled compound (645 mg, 68%) as a pale yellow solid.

المصدر