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

Participants

Reaction Conditions

Reaction Steps

A solution of 4-iodopyrazole (20 g, 0.10 mol) in anhydrous DMF (300 mL) was treated with Cs2CO3 (32.5 g, 0.10 mol) and 2-(2-bromoethoxy)tetrahydro-2H pyran. The resultant reaction mixture was stirred at 70° C. overnight. The cooled mixture was diluted with EtOAc (500 mL) and water (500 mL). The layers were separated and the aqueous layer was extracted with EtOAc (3×500 mL). The combined organic layers were washed with water, dried over Na2SO4, and concentrated to afford yellow oil. Purification on a silica gel provided 4-iodo-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazole (22 g, 66.2% yield). 1H-NMR (300 MHz, CDCl3): δ 7.55 (s, 1H), 7.50 (s, 1H), 4.53 (s, 1H), 4.33 (m, 2H), 4.03 (m, 1H), 3.74 (m, 1H), 3.61 (m, 1H), 3.46 (m, 1H), 1.60-1.48 (m, 6H).

Provenance & Evidence