반응 #674280

반응 방정식

ethyl 4-bromo-1-(3,4-difluorophenyl)-1H-pyrazole-3-carboxylate

methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

potassium carbonate

→

Ethyl 1-(3,4-difluorophenyl)-4-[3-(ethoxycarbonyl)phenyl]-1H-pyrazole-3-carboxylate

용매

ethanol

반응 조건

후처리

1. 1
   온도heated at the boil for 4 h
2. 2
   기타the solvent was removed under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue was dissolved in water
4. 4
   기타dichloromethane, the phases were separated
5. 5
   건조the organic phase was dried over magnesium sulfate
6. 6
   기타The crude product was purified by chromatography (ethyl acetate:n-heptane 1:4)

실험 절차

180 mg (0.54 mmol) of ethyl 4-bromo-1-(3,4-difluorophenyl)-1H-pyrazole-3-carboxylate, 156.7 mg (0.59 mmol) of methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate, 158 mg (1.14 mmol) of potassium carbonate, 5.07 mg (0.011 mmol) of 2,2-dicyclohexylphosphino-2″,6″-diisopropoxybiphenyl and 1.22 mg (0.005 mmol) of palladium (II)acetate were suspended in 5 ml of ethanol and heated at the boil for 4 h. After cooling to room temperature, the solvent was removed under reduced pressure, the residue was dissolved in water and dichloromethane, the phases were separated and the organic phase was dried over magnesium sulfate. The crude product was purified by chromatography (ethyl acetate:n-heptane 1:4). This gave 84 mg (37%) of the desired product. 1H-NMR (400 MHz, CDCl3 δ, ppm) 8.15 (s, 1H); 8.05 (d, 1H); 7.96 (s, 1H); 7.74-7.69 (m, 2H); 7.53-7.47 (m, 2H); 7.28 (m, 1H); 4.48-4.34 (m, 4H); 1.43 (t, 3H); 1.29 (t, 3H)

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