Sulfuric Acid → HCID 117815102, compound

Participants

Reaction Conditions

Reaction Steps

A 500 mL 3 neck RBF equipped with mechanical stirrer, reflux condenser, and addition funnel was charged with 6-chloro-3′-fluoro-[2,2′-bipyridin]-3-amine (6.63 g, 29.6 mmol). It was treated with 2M sulfuric acid (111 mL, 222 mmol) creating a yellow/orange solution. The reaction was cooled to −5° C. and treated dropwise with a solution of sodium nitrile (2.66 g, 38.5 mmol) in 49 mL water at −5° C. The yellow/orange suspension was stirred at 0° C. for 30 minutes, then treated dropwise with a solution of potassium iodide (14.76 g, 89 mmol) in 63 mL of water. The reaction was stirred at room temperature for 30 minutes, then heated to 80° C. for 1 hour. After cooling, the reaction was extracted with EtOAc, washed with water, 2M Na2CO3, NaHSO3, and brine, dried over sodium sulfate, filtered, and concentrated. The crude product was purified by column chromatography using 20% EtOAc/hexanes to give 6-chloro-3′-fluoro-3-iodo-2,2′-bipyridine (16 g, 81% yield).

Provenance & Evidence