Potassium Iodide → 5-Fluoro-3-iodo-1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridine

Participants

Reaction Conditions

Reaction Steps

5.0 g (19.010 mmol) of 5-fluoro-3-iodo-1H-pyrazolo[3,4-b]pyridine were initially charged in DMF (100 ml), and then 20.83 g (76.042 mmol) of 1,1,1,2,2-pentafluoro-4-iodobutane, and also 14.86 g (45.65 mmol) of cesium carbonate and 0.63 g (3.802 mmol) of potassium iodide were added. The mixture was stirred at 140° C. overnight. The mixture was then cooled and combined with a prior experiment which proceeded analogously from 200 mg of 5-fluoro-3-iodo-1H-pyrazolo[3,4-b]pyridine. Solids were filtered off with suction and washed with DMF, and then the liquid was concentrated under high vacuum. The residue was purified by means of preparative HPLC (methanol:water gradient). This gave 4.34 g (52% of theory) of the title compound in solid form.

Provenance & Evidence