(2,3,5,6-tetrafluorophenyl)hydrazine

Conditions: temp:184.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. The reaction mixture was flushed with argon securely capped 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) 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) the combined organic layers were dried over sodium sulfate evaporated in vacuo