Example 10: Synthesis of 1.2-(4,6-difluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxyisopropylamide
Step 1: Synthesis of 4,6-difluoro-3-iodo-1H-indazole
At room temperature, 4,6-difluoro-1H-indazole (1.16 g, 7.53 mmol) was dissolved in DMF (60 mL) and potassium hydroxide (1.27 g, 22.6 mmol) and iodine (2.87 g, 11.3 mmol) were added sequentially. The reaction mixture was stirred at room temperature for 2 h. The reaction solution was maroon in color. After completion of the reaction, the reaction was quenched with 10% Na2S2O3 aqueous solution and diluted with water. The mixture was extracted with EtOAc (2×). The organic phases were combined, washed sequentially with water, saturated LiCl solution and saturated NaCl solution, dried over MgSO4 and concentrated to give 4,6-difluoro-3-iodo-1H-indazole (2.18 g) as a light brown solid.
