Dimethylformamide → 1-{[(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]methyl}-4-iodo-1H-pyrazole

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-iodopyrazole (1.00 g, 5.16 mmol), (R)-(−)-(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl p-toluenesulfonate (1.624 g, 5.671 mmol), Cs2CO3 (2.52 g, 7.73 mmol) and DMF (8 mL, 100 mmol) was heated to 100° C. for 2 h. The solution was extracted with EtOAc, and washed with water (2×). The organic layer was concentrated in vacuo and purified via column chromatography, eluting with 2-10% EtOAc/hexanes. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. MS (ES+): m/z=309.00 (100) [MH+]. HPLC: tR=1.32 min (polar—3 min, UPLC-ACQUITY).

Provenance & Evidence