3-Bromo-6-chloro-1H-indazole

698-25-9

885521-34-6

Step 1a. 6-Chloro-1H-indazole (3.0 g, 19.66 mmol) was suspended in 2 M NaOH solution (70 mL) and a solution of bromine (2.32 g, 14.52 mmol) in 2 M NaOH (30 mL) was added slowly and dropwise. The reaction mixture was stirred at room temperature for 1.5 hours. Upon completion of the reaction, the pH was adjusted to 8 with 3 M HCl, followed by liquid-liquid partitioning with ethyl acetate and brine. The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate/petroleum ether) to afford the target compound 3-bromo-6-chloro-1H-indazole as a yellow solid (3.4 g, 44% yield).ESI-MS m/z = 231.00, 233.00 [M + H]+.