Reaktion #42442

Reaktionsgleichung

1-iodobutane

NaH

methyl 1H-indazole-6-carboxylate

1-iodobutane

→

title compound

Methyl 1-butyl-1H-indazole-6-carboxylate

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated at 60° C. for 72 h
2. 2
   SonstigeThe mixture was removed
3. 3
   Temperaturfrom heat
4. 4
   Temperaturcooled to room temperature
5. 5
   Sonstigepartitioned between water and ethyl acetate
6. 6
   SonstigeThe layers were separated
7. 7
   Waschenthe organic layer washed three times with brine
8. 8
   Trocknendried over anhydrous magnesium sulfate
9. 9
   Einengenconcentrated under reduced pressure

Vorschrift

To a mixture of methyl 1H-indazole-6-carboxylate (0.95 g) in DMF (10 mL) was added 60% NaH (0.216 g). The mixture was heated to 60° C. and 1-iodobutane (0.61 mL) was added. The mixture was heated at 60° C. for 72 h and 1-iodobutane (0.61 mL) was added every 24 h. The mixture was removed from heat and cooled to room temperature and partitioned between water and ethyl acetate. The layers were separated and the organic layer washed three times with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Column chromatography on silica gel (100 mL) using 5% ethyl acetate in hexanes as eluent to give 0.356 g of the title compound: 1H NMR (CDCl3) δ 0.938, 1.34, 1.92, 3.97, 4.43, 7.73, 7.79, 8.03, 8.18.

Quelle