Phenethylamine → n-[4-(3h-Imidazo[4,5-c]pyridin-2-yl)-9h-fluoren-9(r,s)-yl]-phenethyl-amine

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Reaction Conditions

Reaction Steps

In a microwave reactor, add 81 μL of 2-phenyl-ethylamine, 18 μL of diethylisopropylamine and 182 μL of titanium tetra-isopropylate to a solution of 84 mg of 4-(3H-imidazo[4,5-c]pyridin-2-yl)-fluoren-9-one, obtained in Example 1, in 0.5 ml of ethanol. Then heat successively at 60° C. for 5 minutes, at 70° C. for 20 minutes, at 100° C. for 15 minutes and finally at 130° C. for 30 minutes. After cooling to room temperature, add 25 mg of sodium cyanohydroborate and stir for 16 hours at room temperature. Pour the reaction mixture into 5 ml of a saturated aqueous solution of potassium dihydrogen phosphate, then extract 3 times with 10 ml of dichloromethane. After purification on silica gel, eluting with mixtures of dichloromethane and methanol (98-2, then 96-4 by volume), we obtain 4.8 mg of N-[4-(3H-imidazo[4,5-c]pyridin-2-yl)-9H-fluoren-9(R,S)-yl]-phenethyl-amine, in the form of a white solid with the following characteristics:

Provenance & Evidence