4-Fluoroiodobenzene → 1-(4-Fluorophenyl)-1H-indazol-4-amine

Participants

Reaction Steps

A mixture of 1H-indazol-4-amine (750 mg, 5.64 mmol), copper (I) iodide (247 mg, 1.3 mmol), potassium carbonate (1.56 g, 11.28 mmol), trans-N,N′-dimethyl-1,2-cyclohexanediamine (0.321 g, 2.26 mmol) and 4-fluoro-1-iodobenzene (0.78 ml, 6.77 mmol) in dry DMF (2 ml) was heated in a microwave reactor at 140° C. for 20 minutes (potassium carbonate was placed in the tube first and care was taken to avoid any particles of potassium carbonate being left on the side of the tube above the level of the liquid (in order to avoid any superheating). Three identical reactions plus two using 500 mg input of 1H-indazol-4-amine were then combined and partitioned between water and dichloromethane. The organic layer was evaporated and the residue purified by silica gel chromatography using the Flashmaster II (2×100 g cartridges) eluting with a 0 to 50% dichloromethane:ethyl acetate gradient over 60 minutes to give the title compound (4.73 g).

Provenance & Evidence