Reacción #42442

Ecuación de reacción

1-iodobutane

NaH

methyl 1H-indazole-6-carboxylate

1-iodobutane

→

title compound

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

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was heated at 60° C. for 72 h
2. 2
   OtroThe mixture was removed
3. 3
   Temperaturafrom heat
4. 4
   Temperaturacooled to room temperature
5. 5
   Otropartitioned between water and ethyl acetate
6. 6
   OtroThe layers were separated
7. 7
   Lavadothe organic layer washed three times with brine
8. 8
   Secadodried over anhydrous magnesium sulfate
9. 9
   Concentraciónconcentrated under reduced pressure

Procedimiento

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.

Fuente