反応 #609307

反応方程式

6-amino-2-bromopyridine

sodium carbonate

water

ethyl 5-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylate

→

title compound

収率 51.0%

Ethyl 5-(5-(6-aminopyridin-2-yl)-2-chlorobenzamido)-1-phenyl-1H-pyrazole-3-carboxylate

収率 51.0%

溶媒

dioxane

反応条件

後処理

1. 1
   その他obtained in Preparation 5
2. 2
   その他The reaction was degassed with nitrogen for 30 minutes before the addition of Pd(dppf)Cl2
3. 3
   その他with further degassing for 10 minutes
4. 4
   温度The reaction was cooled
5. 5
   洗浄eluted through a pad of silica
6. 6
   洗浄eluting with EtOAc (50 mL)
7. 7
   洗浄The organic solution was washed with water (50 mL)
8. 8
   乾燥dried over magnesium sulfate
9. 9
   濃縮concentrated in vacuo
10. 10
    その他The residue was purified
11. 11
    洗浄eluting with 30-50% EtOAc in heptanes

実験手順

6-amino-2-bromopyridine (835.5 mg, 4.83 mmol), sodium carbonate (1.39 g, 13.2 mmol) and water (0.5 mL) were added to the solution of ethyl 5-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylate in dioxane obtained in Preparation 5. The reaction was degassed with nitrogen for 30 minutes before the addition of Pd(dppf)Cl2 with further degassing for 10 minutes. The reaction was heated to 100° C. for 16 hours. The reaction was cooled and eluted through a pad of silica, eluting with EtOAc (50 mL). The organic solution was washed with water (50 mL) dried over magnesium sulfate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 30-50% EtOAc in heptanes to afford the title compound as a pale yellow solid (1.02 g, 51%).

出典