Methanol → 1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide

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Reaction Conditions

Reaction Steps

Trimethylaluminum (2.0M in toluene, 60 mL, 120 mmol) was added dropwise to a suspension of ammonium chloride (6.42 g, 120 mmol) in 180 mL toluene cooled to 0° C. The solution was then stirred at room temperature for 3.5 hours. This solution (0.5M, 146 mL, 72.9 mmol) was then added to the intermediate from Step D above (4.6 g, 15.9 mmol) and then heated at 110° C. for 2.5 hours. The solution was then cooled to room temperature and carefully poured to silica gel (70 g) and methanol (750 mL). After stirring overnight the suspension was filtered and the filtered solid washed with methanol. The filtrate was concentrated in vacuo to give the title compound which was used in the next step without further purification. m/z=308.2 (M+H).

Provenance & Evidence