3-Pentanamine → HCID 178446212, compound

Participants

Reaction Steps

In a 30 mL scintillation vial equipped with a stir bar was added ethyl acetate (10 mL), 5-chloro-3-fluoro-2-nitropyridine (101 mg, 0.56 mmol), and 3-aminopentane (74 mL, 0.63 mmol). The reaction was stirred at room temperature until starting material was consumed (TLC 25% ethyl acetate in hexanes). To this solution was added tin(II) chloride dihydrate (560 mg, 2.5 mmol), and the mixture was stirred until the aryl nitro was completely reduced (4 h to overnight). The solution was transferred from the scintillation vial to a 5 mL microwave tube, followed by the addition of carbonyldiimidazole (>10 equiv). The reaction was heated in a microwave reactor at 150° C. for 20 min. After cooling, water was added, and the organic layer was separated, concentrated, and purified by flash chromatography over silica gel (30-40% ethyl acetate in hexanes) to give 6-chloro-1-(pentan-3-yl)-1H-imidazo[4,5-b]pyridin-2-ol (93 mg, 0.390 mmol, 68% yield).

Provenance & Evidence