2-Aminopyridine → HCID 25120171, compound

Participants

Reaction Steps

To a solution of 4-[(3-hydroxypropyl)amino]-7-(trifluoromethyl)imidazo[1,2-a]quinoxaline-8-carbaldehyde (25 mg; 0.07 mmol; 1 eq), 2-aminopyridine (20 mg; 0.21 mmol; 3 eq) and titanium tetraisopropoxide (60 mg; 0.21 mg; 3 eq) in anhydrous tetrahydrofuran (0.2 ml) with a few 4A molecular sieves stirred under Ar at rt for 5 h is added sodium borohydride (3 mg; 0.07 mmol; 1 eq). The resulting reaction mixture is then stirred under Ar at rt for 16 h. Partition (aqueous ammonium chloride/ethyl acetate), filtration over Celite, extraction of the aqueous phase (ethyl acetate), reunion of the organic phases, drying (magnesium sulphate) and purification by prep CCM on silicagel (dichloromethane/methanol 95:5) affords the title product (7.4 mg; 0.018 mmol; 25%).

Provenance & Evidence