Reacción #643128

Ecuación de reacción

5-isopropyl-2,4-dimethoxy-N-(1-methyl-1H-indol-5-yl)-thiobenzamide

hydrazine

diisopropylethylamine

phenylisocyanide dichloride

→

[5-(5-Isopropyl-2,4-dimethoxy-phenyl)-4-(1-methyl-1H-indol-5-yl)-4H-[1,2,4]triazol-3-yl]-phenyl-amine

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solvent was removed by evaporation
2. 2
   workup.ADDITIONTo the solid cake was added ethyl acetate (10 mL) and 10% aqueous potassium carbonate (1 mL), and it
3. 3
   workup.DISSOLUTIONwas completely dissolved
4. 4
   OtroThe organic layer was isolated
5. 5
   Secadodried with sodium sulfate
6. 6
   workup.STIRRINGThe reaction was stirred overnight
7. 7
   Lavadowashed with saturated aqueous ammonium chloride
8. 8
   Secadodried with sodium sulfate
9. 9
   Otrothe product was purified by column chromatography

Procedimiento

A flask was charged with 5-isopropyl-2,4-dimethoxy-N-(1-methyl-1H-indol-5-yl)-thiobenzamide (123 mg; 0.33 mmol), dioxane (2 mL), and hydrazine (0.5 mL). The reaction was heated to 100° C. for one hour, and the solvent was removed by evaporation. To the solid cake was added ethyl acetate (10 mL) and 10% aqueous potassium carbonate (1 mL), and it was shaken until the solid was completely dissolved. The organic layer was isolated, and dried with sodium sulfate. To the crude intermediate in the organic layer was added diisopropylethylamine (86 mg, 0.66 mmol) and phenylisocyanide dichloride (88 mg; 1.5 eq.). The reaction was stirred overnight, and washed with saturated aqueous ammonium chloride, dried with sodium sulfate, and the product was purified by column chromatography to give [5-(5-Isopropyl-2,4-dimethoxy-phenyl)-4-(1-methyl-1H-indol-5-yl)-4H-[1,2,4]triazol-3-yl]-phenyl-amine (64 mg).

Fuente