Potassium Iodide → 5-iodo-3-(pyridin-4-yl)-1-trityl-1H-indazole

Participants

Reaction Conditions

Reaction Steps

To the stirred solution of 3-(pyridin-4-yl)-1-trityl-1H-indazol-5-amine (6.02 g, 13.3 mmol) in MeCN (45 mL) was added p-toluenesulfonic acid monohydrate (3.37 g, 17.7 mmol). After cooled to 10° C., a solution of sodium nitrite (1.84 g, 26.6 mmol), potassium iodide (5.52 g, 33.2 mmol) in water (9 mL) was added dropwise. The resulting dark brown solution was stirred at room temperature for 4 hours. The mixture was diluted with EtOAc and washed with water and 1N Na2S2O3. After dried and concentrated, the crude mixture was column purified with mixture of hexane and EtOAc to give 5-iodo-3-(pyridin-4-yl)-1-trityl-1H-indazole (3.95 g).

Provenance & Evidence