2,3,5,6-Tetrafluorophenylhydrazine → 4-iodo-1-(2,3,5,6-tetrafluorophenyl)-1H-pyrazolo[3,4-b]pyridine

Participants

Reaction Conditions

Reaction Steps

To a 15 mL pressure bottle was added 2-fluoro-4-iodonicotinaldehyde (710 mg, 2.83 mmol), (2,3,5,6-tetrafluorophenyl)hydrazine (509 mg, 2.83 mmol), and anhydrous NMP (4 mL). The reaction mixture was flushed with argon, securely capped, and heated at 184° C. for 2.75 h. The reaction mixture was partitioned with ethyl acetate (300 mL), water (125 mL), and brine (50 mL). The organic layer was washed with water (4×40 mL) and brine (75 mL) and the combined aqueous layers were extracted with additional ethyl acetate (300 mL). The second organic layer was washed with water (4×60 mL), and brine (100 mL), and the combined organic layers were dried over sodium sulfate, and evaporated in vacuo to give 1.16 g (quantitative yield) of the title compound as a tan solid. LC/MS (Condition B): ret. T=3.92 min, (M+H)+ 393.89.

Provenance & Evidence