Potassium Phosphate, Tribasic → 1-(2-Fluorophenyl)-1H-indazol-4-amine

Participants

Reaction Steps

1H-Indazol-4-amine (1.83 g, 10 mmol), copper (I) iodide (95 mg. 0.5 mmol) and potassium phosphate (4.46 g, 21 mmol) were stirred together. The flask was evacuated and refilled with argon twice. To the flask was then added trans-N,N′-dimethyl-1,2-cyclohexanediamine (320 μL, 2 mmol), 2-fluoro-1-iodobenzene (2.66 g, 12 mmol) and toluene (30 mL) and the mixture was heated at 110° C. overnight. The reaction mixture was diluted with EtOAc, filtered through Celite to remove inorganics and the Celite pad was washed successively with EtOAc until the solvent ran clear. The reaction mixture was evaporated and the residue was purified by column chromatography eluting with dichloromethane then with dichloromethane:EtOAc 9:1 to give the title compound as a yellow oil (1.19 g) which solidified on standing.

Provenance & Evidence