Aluminium lithium hydride → 1-(2,4-difluorophenyl)-N-ethyl-1H-pyrazol-5-amine

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Reaction Conditions

Reaction Steps

At 0° C., a solution of N-(1-(2,4-difluorophenyl)-1H-pyrazol-5-yl)acetamide (2.58 g, 10.88 mmol) in 35 mL of THF was treated with lithium aluminum hydride (22 mL of the 1.0 M solution in THF, 22 mmol). The reaction mixture was stirred at 0° C. for 90 min then quenched with Rochelle's salt. It was extracted with EtOAc (3×100 mL) followed by DCM (2×50 mL). The combined organic solution was dried over MgSO4, filtered and concentrated. Purification of the crude material on an ISCO 80 g column (30-80% EtOAc in hexanes) afforded 1-(2,4-difluorophenyl)-N-ethyl-1H-pyrazol-5-amine (1.21 g, 50% yield) as a light yellow viscous oil. MS (ES+): 224.1 (M+H)+.

Provenance & Evidence