Cesium carbonate → 4-Iodo-1-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)-1H-pyrazole

Reaction equation

Br[CH2:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1.[I:11][C:12]1[CH:13]=[N:14][NH:15][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[I:11][C:12]1[CH:13]=[N:14][N:15]([CH2:2][CH2:3][O:4][CH:5]2[CH2:10][CH2:9][CH2:8][CH2:7][O:6]2)[CH:16]=1

Participants

Procedure

In a 1 L 3-neck flask equipped with magnetic stir bar, nitrogen blanket and internal temperature probe dissolve 2-(2-bromoethoxy)tetrahydro-2H-pyran (34 g, 156 mmol) in acetonitrile (ACN, 400 mL). Add 4-iodopyrazole (29.34 g, 149.74 mmol) followed by cesium carbonate (73.4 g, 223.02 mmol). Stir the mixture at RT for 18 hours. Filter the reaction mixture through CELITE®, wash the filter cake with ACN and concentrate the filtrate to a golden oil. Use without further purification. Yield: 47.819 g (99%). MS (ES) m/z 323 [M+1]+.