Reaktion #743047

Reaktionsgleichung

1,10-phenanthroline

caesium carbonate

1-(4-Iodo-phenyl)-1H-pyrazole

hydrazine carboxylic acid tert-butyl ester

→

title compound

Ausbeute 82.8%

N-(4-Pyrazol-1-yl-phenyl)-hydrazinecarboxylic acid tert-butyl ester

Ausbeute 82.8%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepurged with N2 (g)
2. 2
   Temperaturto cool
3. 3
   Filtrationwas then filtered through a silica pad, which
4. 4
   Waschenwas then washed with ethyl acetate
5. 5
   EinengenThe filtrate was then concentrated to dryness in vacuo
6. 6
   SonstigeThe resultant residue was purified by column chromatography

Vorschrift

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.

Quelle