6-(4-nitro-1H-pyrazol-1-yl)isoquinoline → 1-(isoquinolin-6-yl)-1H-pyrazol-4-amine

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Reaction Steps

A mixture of 6-(4-nitro-1H-pyrazol-1-yl)isoquinoline (367 mg, 1.53 mmol) and 10 wt. % palladium on activated carbon (163 mg, 153 μmol) in THF (15 mL) was stirred under an atmosphere of hydrogen at ambient temperature for 4 hours. The mixture was filtered through a Celite pad that was washed with THF (30 mL), and the combined filtrates were concentrated under reduced pressure. The resulting yellow solid was dissolved in MeOH/DCM, evaporated onto silica gel, and purified by flash chromatography (Biotage Si 40+M, 3% to 8% MeOH/DCM) to provide 1-(isoquinolin-6-yl)-1H-pyrazol-4-amine (264 mg, 82% yield) as a yellow solid. LCMS (API-ES) m/z (%): 211.2 (100%, M++H); 1H NMR (300 MHz, CDCl3) δ ppm 3.01 (br s, 2H), 7.48 (s, 1H), 7.62-7.69 (m, 2H), 7.93 (s, 1H), 7.96-8.06 (m, 2H), 8.52 (d, J=5.8 Hz, 1H), 9.22 (s, 1H).

Provenance & Evidence