Stannous Chloride → 3-chloro-6-fluoro-1H-indazol-5-amine

Participants

Reaction Conditions

Reaction Steps

The product from Step 1 (575 mg, 2.667 mmol, 1.0 equiv) was dissolved in 15 mL EtOH and SnCl2 (2.5 g, 13.337 mmol, 5.0 equiv) was added. The reaction mixture was heated to 70° C. for 4 hours. The reaction mixture was diluted with EtOAc and 6N NaOH, filtered through a pad of celite and washed with EtOAc and water. The phases of the filtrate were separated, and the organic phase was washed once with satd. NaHCO3, and once with satd. NaCl. The organic phase was dried over Na2SO4, filtered, and concentrated en vacuo. The residue was purified by flash chromatography (20-100% EtOAc in Hexanes) to provide 250 mg (51%) of the title compound as a yellow solid. MS (ES+) m/e 186 [M+H]+

Provenance & Evidence