3-Amino-1-propanol → 3-{[7-(Trifluoromethyl)imidazo[1,2-a]quinoxalin-4-yl]amino}propan-1-ol

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Reaction Steps

To a solution of 4-chloro-7-(trifluoromethyl)imidazo[1,2-a]quinoxaline (2.00 g; 7.36 mmol; 1 eq) in anhydrous dioxane (250 mL), 3-aminopropanol (6.2 mL; 81.0 mmol; 11 eq) is added, under argon atmosphere. Complete conversion was achieved after 17 hours of stirring under reflux. The initially cloudy yellow solution turns first orange and then becomes translucid. The reaction mixture is cooled to room temperature and diluted in ethyl acetate (500 mL). The organic phase is washed three times with a solution of saturated sodium hydrogenocarbonate (3×330 mL). The organic phases are combined, dried over sodium sulfate and concentrated under vacuum to provide pure title compound (1.94 g; 6.25 mmol; 85%) as a grey powder.

Provenance & Evidence