Reaktion #40574

Reaktionsgleichung

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

cyclopropylboronic acid

potassium phosphate

→

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

Lösungsmittel

toluene

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   Extraktionextracted several times with ethyl acetate
3. 3
   Extraktionthe combined organic phases are extracted once more with saturated sodium chloride solution
4. 4
   Sonstigedried
5. 5
   SonstigeThe crude product is purified by RP HPLC (acetonitrile (+0.05% HCOOH)/water (+0.05% HCOOH))

Vorschrift

100 mg of 6-(2-chloropyrimidin-4-yl)-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one, 29.2 mg of cyclopropylboronic acid and 138 mg of potassium phosphate are dissolved in 1 ml of toluene and 0.05 ml of water and, under an argon atmosphere, 17 mg of 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride (1:1 complex with CH2Cl2) are added. The mixture is stirred at 100° C. for 9 h. After cooling to room temperature, it is diluted with 15 ml of water and extracted several times with ethyl acetate, and the combined organic phases are extracted once more with saturated sodium chloride solution and dried using a Varian Chem Elut CE 1005 cartridge. The crude product is purified by RP HPLC (acetonitrile (+0.05% HCOOH)/water (+0.05% HCOOH)).

Quelle