Reacción #2439959

Ecuación de reacción

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

Rendimiento 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

Rendimiento 55.0%

Disolventes

EtOAc

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente