Sodium Iodide → 5-Iodo-1H-indazole

5-Bromo-1H-indazole (2.0 g, 10.15 mmol) was dissolved in dioxane (50 ml) and stirred under N2 atmosphere. Copper iodide (97 mg, 0.51 mmol), sodium iodide (3.04 g, 20.3 mmol) and trans-1,2-bis-(methylamino)-cyclohexane (147 mg, 1.02 mmol) was added and the reaction mixture was stirred for 68 hours at 110° C. The cooled solution was filtered and the filtrate concentrated under reduced pressure. The residue was dissolved in DCM (20 mL) and extracted with aqueous ammonia (1M, 5×10 mL). The organic phase was then washed three times with an aqueous Na2S2O3 solution, dried over MgSO4, filtered and concentrated under reduced pressure to give the product as a white solid (2.43 g, 100%).

1. stirringthe reaction mixture was stirred for 68 hours at 110° C
2. filtrationThe cooled solution was filtered
3. concentrationthe filtrate concentrated under reduced pressure
4. dissolutionThe residue was dissolved in DCM (20 mL)
5. extractionextracted with aqueous ammonia (1M, 5×10 mL)
6. washThe organic phase was then washed three times with an aqueous Na2S2O3 solution
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD record

ord-3e1b9f6953f4451c95796ed8ac39025b

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507469B2