Sodium Iodide → 4-Iodo-1,5-naphthyridine

Participants

Reaction Conditions

Reaction Steps

4-bromo-1,5-naphthyridine (99 mg, 0.47 mmol), copper(I) iodide (4.5 mg, 0.024 mmol) and sodium iodide (142 mg, 0.947 mmol) were combined into one vial fitted with a Teflon septum. The vial was flushed with nitrogen and 1,4-dioxane (4 ml) was added. After sparging with nitrogen for 5 minutes, rac-trans-N,N′-dimethylcyclohexane-1,2-diamine (7.5 μl, 0.047 mmol) was added and the reaction was heated to 100° C. for 12 hours. The mixture was cooled to ambient temperature, and saturated aqueous ammonium chloride (2 ml) was added to quench the reaction. After stirring for 10 minutes, the mixture was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate. The organic layer was separated, and the aqueous layer was back extracted with ethyl acetate one more time. The combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (methanol/dichloromethane gradient) to afford 4-iodo-1,5-naphthyridine.

Provenance & Evidence