反応 #674280

反応方程式

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

溶媒

ethanol

反応条件

後処理

1. 1
   温度heated at the boil for 4 h
2. 2
   その他the solvent was removed under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue was dissolved in water
4. 4
   その他dichloromethane, the phases were separated
5. 5
   乾燥the organic phase was dried over magnesium sulfate
6. 6
   その他The crude product was purified by chromatography (ethyl acetate:n-heptane 1:4)

実験手順

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)

出典