Reacción #40564

Ecuación de reacción

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

bis(pinacolato)diboron

potassium acetate

→

6-Oxo-1-(2-trimethylsilanylethoxymethyl)-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-1,6-dihydropyridazine-3-boronic acid

Disolventes

DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solution is degassed with argon
2. 2
   workup.ADDITIONFor workup, 600 ml of water are added
3. 3
   Extracciónthe mixture is extracted several times with dichloromethane
4. 4
   Lavadothe organic phase is washed with saturated sodium chloride solution
5. 5
   Otrodried
6. 6
   workup.DISTILLATIONAfter the solvent has been distilled off
7. 7
   Otrothe crude product is purified by preparative RP-HPLC (0-100% acetonitrile in water (+0.01% trifluoroacetic acid))

Procedimiento

4 g of 6-chloro-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanylethoxy-methyl) -1H-benzimidazol-2-yl]-2H-pyridazin-3-one (example 46), 4.1 g of bis(pinacolato)diboron, 0.19 g of (1,1 ′-bis(diphenylphosphine)-ferrocene)palladium(II) chloride-dichloromethane complex and 2.3 g of potassium acetate are dissolved in 60 ml of DMSO. The solution is degassed with argon and heated at 95° C. for 2.5 hours. For workup, 600 ml of water are added, the mixture is extracted several times with dichloromethane and the organic phase is washed with saturated sodium chloride solution and dried using a phase separator cartridge. After the solvent has been distilled off, the crude product is purified by preparative RP-HPLC (0-100% acetonitrile in water (+0.01% trifluoroacetic acid)).

Fuente