Reacción #2439962

Ecuación de reacción

2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid

thionyl chloride

5-(4-Amino-benzyl)-1,3-dihydro-indol-2-one

→

product

Rendimiento 44.9%

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

Rendimiento 44.9%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe thionyl chloride was then removed by distillation
2. 2
   TemperaturaThe crude acid chloride was cooled to 65° C.
3. 3
   workup.DISSOLUTIONdissolved in THF (5 mL)
4. 4
   Temperaturato reflux overnight
5. 5
   Temperaturato cool to room temperature
6. 6
   OtroThe room temperature reaction mixture
7. 7
   Concentraciónwas concentrated in vacuo
8. 8
   workup.DISSOLUTIONthe crude residue was dissolved in EtOH (5 mL)
9. 9
   workup.ADDITIONThe ethanolic solution was treated with 1M NaOH(aq) (2 mL)
10. 10
    workup.STIRRINGstirred for 30 min
11. 11
    Otroyielding a pale yellow precipitate
12. 12
    FiltraciónThe pale yellow solids were filtered

Procedimiento

A dry 25 mL flask was charged with 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid (0.168 g, 1.09 mmol) and thionyl chloride (4 mL) and allowed to stir at 79° C. for 2 h. The thionyl chloride was then removed by distillation. The crude acid chloride was cooled to 65° C., and then dissolved in THF (5 mL). 5-(4-Amino-benzyl)-1,3-dihydro-indol-2-one (0.200 g, 0.840 mmol) was added to the THF solution of the acid chloride, and the mixture was allowed to reflux overnight. Subsequently, the reaction mixture was allowed to cool to room temperature. The room temperature reaction mixture was concentrated in vacuo, and the crude residue was dissolved in EtOH (5 mL). The ethanolic solution was treated with 1M NaOH(aq) (2 mL) and stirred for 30 min. The basic solution was acidified to a pH of 1 with 1M HCl(aq) yielding a pale yellow precipitate. The pale yellow solids were filtered to afford the pure product (0.141 g, 0.377 mmol, 34.5%).

Fuente