Hydrogen Peroxide → 2-[(3-hydroxypropyl)amino]-4-{4-[6-(trifluoromethyl)pyridin-3-yl]-9H-carbazol-9-yl}benzamide

Participants

Reaction Conditions

Reaction Steps

0.17 g of potassium carbonate and 0.64 ml of 3-amino-1-propanol are successively added to a solution of 0.18 g of 2-fluoro-4-{4-[6-(trifluoromethyl)pyridin-3-yl]-9H-carbazol-9-yl}benzonitrile in 2 ml of dimethyl sulphoxide. The reaction mixture is heated at 90° C. for 1 hour 20 minutes in a microwave, and then 4.2 ml of ethanol are added, followed by 0.8 ml of a 1N solution of sodium hydroxide and 0.8 ml of 30% aqueous hydrogen peroxide. The reaction mixture is stirred at ambient temperature for 2 hours and then diluted with distilled water. The aqueous phase is extracted twice with ethyl acetate and the combined organic phases are washed with water and a saturated solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure. The white solid obtained is purified by silica gel chromatography, elution being carried out with a mixture of dichloromethane, acetonitrile and methanol (96/2/2 by volume) so as to give 24 mg of 2-[(3-hydroxypropyl)amino]-4-{4-[6-(trifluoromethyl)pyridin-3-yl]-9H-carbazol-9-yl}benzamide in the form of a white solid, the characteristics of which are the following

Provenance & Evidence