Реакция #674280

Уравнение реакции

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

Растворители

ethanol

Условия реакции

Обработка

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

Методика

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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