反応 #609299

反応方程式

2,4-dichloro-5-(3-fluoropyridin-2-yl)benzoic acid

ethyl 5-amino-1-phenyl-1H-pyrazole-3-carboxylate

N,N-diisopropylethylamine

2-methyltetrahydrofuran

propylphosphonic anhydride

→

title compound

収率 79.0%

Ethyl 5-(2,4-dichloro-5-(3-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylate

収率 79.0%

溶媒

water

反応条件

後処理

1. 1
   温度the reaction maintained
2. 2
   温度at reflux for 6 hours
3. 3
   抽出extracted with 2-methyltetrahydrofuran (2×1.5 L)
4. 4
   濃縮The combined organic layers were concentrated in vacuo
5. 5
   その他to provide a slurry which
6. 6
   ろ過was filtered
7. 7
   洗浄the solid washed with ethyl acetate (3×200 mL)

実験手順

To a refluxing mixture of 2,4-dichloro-5-(3-fluoropyridin-2-yl)benzoic acid (Preparation 27A, 159 g, 0.554 mol), ethyl 5-amino-1-phenyl-1H-pyrazole-3-carboxylate (154 g, 0.665 mol), N,N-diisopropylethylamine (215 g, 1.66 mol) and 2-methyltetrahydrofuran (4.8 L), was added propylphosphonic anhydride solution (989 mL, 1.66 mol, >50% by weight in EtOAc) and the reaction maintained at reflux for 6 hours. After cooling to room temperature, the reaction was diluted with water (6 L) and extracted with 2-methyltetrahydrofuran (2×1.5 L). The combined organic layers were concentrated in vacuo to provide a slurry which was filtered and the solid washed with ethyl acetate (3×200 mL) to give the title compound as a white solid (215 g, 79%).

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