Sulfuric Acid → HCID 117815102, compound

Temperature

-5 °C

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).

1. temperaturereflux
2. additioncondenser, and addition funnel
3. stirringThe reaction was stirred at room temperature for 30 minutes
4. temperatureheated to 80° C. for 1 hour
5. temperatureAfter cooling
6. extractionthe reaction was extracted with EtOAc
7. washwashed with water, 2M Na2CO3, NaHSO3, and brine
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customThe crude product was purified by column chromatography

ORD record

ord-00bc8bd3e4ec4307a5b2467d0c9e6717

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09324949B2