Under an atmosphere of nitrogen, sodium hydride (5 mg, 0.14 mmol, 60% suspension in mineral oil) was added to a solution of tetrahydro-2H-pyran-4-ol (13 mg, 0.14 mmol) in THF (2 ml). After hydrogen evolution was complete, 6-Fluoro-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide (50 mg, 0.14 mmol) was added and the mixture was heated to reflux for 1 h. Another portion of tetrahydro-2H-pyran-4-ol (13 mg, 0.14 mmol) and sodium hydride (5 mg, 0.14 mmol) was added and the mixture was heated to reflux overnight. The mixture was cooled to room temperature, water was added and the mixture was extracted with DCM. The organic extracts were combined, dried over MgSO4, filtered and the solvent was removed in vacuo to give an orange oil. This was purified by mass-directed automated preparative HPLC (Method B) to give the title compound (7 mg) as a white solid.
