Methylhydrazine → 4-Iodo-1-methyl-1H-indazol-3-amine

Participants

Reaction Conditions

Reaction Steps

To a 330 mL pressure vessel equipped with a magnetic stir bar was added 2-fluoro-6-iodobenzonitrile (4.5 g, 18.2 mmol), N,N-dimethylacetamide (45 mL), and methylhydrazine (1.2 mL 23.7 mmol). The vessel was flushed with N2 gas, sealed and heated at 87° C. overnight and at 120° C. for 5 h. The reaction mixture was cooled, diluted with EtOAc (300 mL, and washed with water. The aqueous layer was extracted and the combined EtOAc extracts were washed with water (3×150 mL), brine, dried (Na2SO4), filtered and concentrated to a brown solid. The solid was triturated with EtOAc/hexanes (1:1, 10 mL), filtered, washed with EtOAc/hexanes (1:1) and dried to give 4.04 g (81%) of I-216 as a beige solid. 1H NMR (400 MHz, DMSO-d6)

Provenance & Evidence