Sodium Carbonate → 4-[6-(4-Fluorophenyl)imidazo[1,2-a]pyrimidin-7-yl]-benzaldehyde

Participants

Reaction Conditions

Reaction Steps

2.8 g (11.3 mmol) 7-Chloro-6-(4-fluorophenyl)-imidazo[1,2-a]pyrimidine are given in 39 mL dimethoxyethane (not completely dissolved). 1.86 g (12.4 mmol) 4-formylphenylboronic acid and 22 mL Na2CO3 solution (10%) are added. After addition of 0.42 g (0.51 mmol) 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium(II) the reaction mixture is purged 3× with argon and heated to 90° C. After 22 h stirring at 90° C. complete dissolution has taken place. The reaction mixture is cooled down and treated with 100 mL water and 150 mL dichloromethane. After vigorous stirring at rt for one hour the organic phase is separated. The aqueous phase is extracted twice with dichloromethane (100 mL each). The combined organic phases are washed twice with water (50 mL each), dried (Na2SO4) and the solvent is removed. The crude product is purified via chromatography (silicagel, dichloromethane/methanol). 1.52 g (42.4%) of the pure compound and two other fractions (224.6 mg=6.3% and 456.9 mg=12.7%) with contaminated product are obtained.

Provenance & Evidence