Hydrogen Peroxide → 2-[(3-hydroxypropyl)amino]-4-[4-(5-methoxypyridin-3-yl)-9H-carbazol-9-yl]benzamide

Participants

Reaction Conditions

Reaction Steps

0.85 g of potassium carbonate and 3.14 ml of 3-amino-1-propanol are successively added to a solution of 0.81 g of 2-fluoro-4-[4-(5-methoxypyridin-3-yl)-9H-carbazol-9-yl]benzonitrile obtained in stage 2 of Example 27, in 7 ml of dimethyl sulphoxide. The reaction mixture is heated at 90° C. for 1 hour and 20 minutes in a microwave, and then 20.9 ml of ethanol are added, followed by 4 ml of a 1N solution of sodium hydroxide and 4 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 trituration in diisopropyl ether, so as to give 0.45 g of 2-[(3-hydroxypropyl)amino]-4-[4-(5-methoxypyridin-3-yl)-9H-carbazol-9-yl]benzamide in the form of a white solid, the characteristics of which are the following:

Provenance & Evidence