Sodium Iodide → HCID 178505979, compound

Participants

Reaction Conditions

Reaction Steps

10 g (65.75 mmol) of 5-fluoro-1H-pyrazolo[3,4-b]pyridine-3-amine were initially charged in THF (329 ml), and the mixture was cooled to 0° C. 16.65 ml (131.46 mmol) of boron trifluoride/diethyl ether complex were then added slowly. The reaction mixture was cooled further to −10° C. A solution of 10.01 g (85.45 mmol) of isopentyl nitrite in THF (24.39 ml) was then added slowly, and the mixture was stirred for a further 30 min. The mixture was diluted with cold diethyl ether (329 ml) and the resulting solid was filtered off. The diazonium salt prepared in this manner was added a little at a time into a solution of 12.81 g (85.45 mmol) of sodium iodide in acetone (329 ml) at 0° C., and the mixture was stirred at RT for 30 min. The reaction mixture was added to ice-water (1.8 l) and extracted twice with ethyl acetate (487 ml each). The collected organic phases were washed with saturated aqueous sodium chloride solution (244 ml), dried, filtered and concentrated. This gave 12.1 g (86% pure, 60% of theory) of the title compound as a solid. The crude product was reacted without further purification.

Provenance & Evidence