6-Fluoro-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide (100 mg, 0.27 mmol) and tetrahydro-2H-pyran-4-amine (55 mg, 0.54 mmol) were dissolved in DMSO (1.5 ml) in a microwave vial. DIPEA (0.282 ml) was added and the mixture was heated at 160° C. for 3 h under microwave irradiation. The reaction mixture was concentrated under a stream of nitrogen and redissolved in methanol. This solution was loaded onto a 2 g aminopropyl column, which was been preconditioned with methanol. The column was eluted with methanol (2 column volumes) and the desired fraction was blown to dryness under nitrogen. The sample was then purified by Mass Directed Automated Preparative HPLC (Method B) to give the title compound (57 mg) as a white solid.
