反応 #2439959

反応方程式

2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indol-5-ylmethyl)-phenyl]-amide

THF

4-(4-Methyl-piperazin-1-yl)-phenylamine

→

desired product

収率 55.0%

2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(3-{[4-(4-methyl-piperazin-1-yl)-phenylamino]-methylene}-2-oxo-2,3-dihydro-1H-indol-5-ylmethyl)-phenyl]-amide

収率 55.0%

溶媒

EtOAc

反応条件

後処理

1. 1
   その他A small screw cap test tube
2. 2
   温度Subsequently, the reaction mixture was cooled to room temperature
3. 3
   洗浄The solution was washed with water (2 mL)
4. 4
   洗浄the water layer was re-washed with additional EtOAc (2 mL)
5. 5
   濃縮The combined organic layers were then concentrated in vacuo
6. 6
   その他affording the crude product
7. 7
   その他The crude product was further purified by silica gel column chromatography with 5% methanol in chloroform as eluant

実験手順

A small screw cap test tube was charged with 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indol-5-ylmethyl)-phenyl]-amide (prepared below, 70 mg, 0.175 mmol) and THF (1 mL). To the resulting solution was added 4-(4-Methyl-piperazin-1-yl)-phenylamine (66.8 mg, 0.349 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature and then diluted with EtOAc (2 mL). The solution was washed with water (2 mL) and the water layer was re-washed with additional EtOAc (2 mL). The combined organic layers were then concentrated in vacuo affording the crude product. The crude product was further purified by silica gel column chromatography with 5% methanol in chloroform as eluant to give the desired product as a solid in 55% yield (55 mg, 0.96 mmol).

出典