1,10-Phenanthroline → N-(4-Pyrazol-1-yl-phenyl)-hydrazinecarboxylic Acid tert-butyl Ester

Participants

Reaction Conditions

Reaction Steps

Copper iodide (18 mg, 0.05 eq, 0.09 mmol), 1,10-phenanthroline (67 mg, 0.2 eq, 0.37 mmol) and caesium carbonate (0.84 g, 1.4 eq, 2.6 mmol) were mixed in a RB flask, placed under vacuum and purged with N2 (g). 1-(4-Iodo-phenyl)-1H-pyrazole (0.5 g, 1.0 eq, 1.85 mmol), hydrazine carboxylic acid tert-butyl ester (0.3 g, 1.2 eq, 2.22 mmol) and DMF (25 ml) were added to the mixture which was then heated to 80° C. with stirring under an inert atmosphere for 21 hours. The reaction mixture was allowed to cool and was then filtered through a silica pad, which was then washed with ethyl acetate. The filtrate was then concentrated to dryness in vacuo. The resultant residue was purified by column chromatography using heptane/ethyl acetate (3:1) as eluent to yield impure title compound (0.42 g). LCMS: [M+H]+=275, rt=1.25 min, 48% purity.

Provenance & Evidence