Reacción #40562

Ecuación de reacción

6-chloro-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one

thiophene-3-boronic acid

potassium carbonate

water

→

6-Thiophen-3-yl-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanyl-ethoxymethyl) -1H-benzimidazol-2-yl]-2H-pyridazin-3-one

Disolventes

dimethoxyethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrofor degassing
2. 2
   workup.ADDITIONAddition of 7 mg of (1,1′-bis(diphenylphosphine) -ferrocene)palladium(II) chloride-dichloromethane complex
3. 3
   workup.ADDITIONFor workup, it is diluted with water
4. 4
   Extracciónextracted several times with ethyl acetate
5. 5
   OtroThe combined organic phases are dried
6. 6
   workup.DISTILLATIONthe solvent is distilled off
7. 7
   OtroThe crude product is purified by silica gel chromatography (n-heptane/ethyl acetate)

Procedimiento

44 mg of 6-chloro-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one, 14 mg of thiophene-3-boronic acid and 36 mg of potassium carbonate are dissolved 1.5 ml of a 1:2 mixture of water and dimethoxyethane, and argon is passed through the solution for degassing. Addition of 7 mg of (1,1′-bis(diphenylphosphine) -ferrocene)palladium(II) chloride-dichloromethane complex is followed by stirring at 85° C. for 4 hours. For workup, it is diluted with water and extracted several times with ethyl acetate. The combined organic phases are dried using a silica gel cartridge, and the solvent is distilled off. The crude product is purified by silica gel chromatography (n-heptane/ethyl acetate).

Fuente