Tetrahydrofuran → HCID 178431103, compound

Participants

Reaction Steps

To a solution of 1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-5-fluoro-4-iodo-1H-pyrazole (80.0 mg, 0.188 mmol) in THF (2 mL, 20 mmol) at rt was added 1.3 M of isopropylmagnesium chloride in THF (0.58 mL, 0.75 mmol), and the mixture was stirred for 1 h. The reaction was quenched with 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.15 mL, 0.94 mmol), and allowed to stir at rt for 1 h. Sat. NH4Cl was added, and the organic solvent was removed in vacuo. The material was extracted with DCM and water. The organic layer was dry-loaded onto silica gel and purified via column chromatography, eluting with 2-7% 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=425.28 (100) [MH+]. HPLC: tR=2.23 min (polar—3 min, UPLC-ACQUITY).

Provenance & Evidence