Reacción #306461

Ecuación de reacción

cesium carbonate

4-iodopyrazole

2-(2-bromoethoxy)tetrahydro-2 h-pyran

→

4-iodo-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazole

Disolventes

DMF

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with EtOAc (3×50 mL)
2. 2
   Lavadosubsequently washed with water (2×50 mL) and brine
3. 3
   Secadodried over sodium sulfate
4. 4
   Filtraciónfiltered
5. 5
   OtroThe crude mixture was evaporated onto silica gel
6. 6
   Otropurified via MPLC (0% to 50%; EtOAc in hexanes)

Procedimiento

A mixture of cesium carbonate (20.7 g, 63.4 mmol) and 4-iodopyrazole (10.00 g, 51.6 mmol) in DMF (100 mL) was allowed to stir for 10 min. To the mixture was added 2-(2-bromoethoxy)tetrahydro-2 h-pyran (9.98 ml, 63.4 mmol) and heated at 80° C. overnight. The mixture was diluted with water and extracted with EtOAc (3×50 mL), and subsequently washed with water (2×50 mL) and brine, dried over sodium sulfate, and filtered. The crude mixture was evaporated onto silica gel and purified via MPLC (0% to 50%; EtOAc in hexanes). Isolated 4-iodo-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazole (15.3 g, 92%) as a clear oil. MS m/z=323.0 [M+1]+. Calc'd for C10H15IN2: 322.1.

Fuente