تفاعل #974925

معادلة التفاعل

methyl 5-bromo-2,3-dimethyl-2H-indazole-4-carboxylate

triphenylphosphine

potassium carbonate

methyl acrylate

→

title compound

المردود 54.0%

methyl 5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-2,3-dimethyl-2H-indazole-4-carboxylate

المردود 54.0%

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvent was evaporated under reduced pressure
2. 2
   workup.ADDITIONthe residue was diluted with ethyl acetate
3. 3
   غسيلwashed with water and saturated brine
4. 4
   تجفيفdried over anhydrous sodium sulfate
5. 5
   أخرىThe solvent was evaporated under reduced pressure
6. 6
   أخرىthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80→60/40)

الإجراء التجريبي

A suspension of methyl 5-bromo-2,3-dimethyl-2H-indazole-4-carboxylate (1.10 g, 3.89 mmol), palladium acetate (87.3 mg, 0.389 mmol), triphenylphosphine (204 mg, 0.778 mmol), potassium carbonate (591 mg, 4.28 mmol) and methyl acrylate (523 μL, 5.83 mmol) in N,N-dimethylformamide (39 mL) was stirred with heating at 100° C. for 4 hr. The solvent was evaporated under reduced pressure, and the residue was diluted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80→60/40) to give the title compound (606 mg, yield 54%).

المصدر