Реакция #2439959

Уравнение реакции

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

Выход 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

Выход 55.0%

Растворители

EtOAc

Условия реакции

Обработка

1. 1
   ДругоеA small screw cap test tube
2. 2
   ТемператураSubsequently, the reaction mixture was cooled to room temperature
3. 3
   ПромывкаThe solution was washed with water (2 mL)
4. 4
   Промывкаthe water layer was re-washed with additional EtOAc (2 mL)
5. 5
   КонцентрированиеThe combined organic layers were then concentrated in vacuo
6. 6
   Другоеaffording the crude product
7. 7
   ДругоеThe crude product was further purified by silica gel column chromatography with 5% methanol in chloroform as eluant

Методика

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).

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