Dimethylformamide → HCID 178455356, compound

Participants

Reaction Steps

A solution of 1-[4-(tert-butyl-dimethylsilanyloxy)-cyclohexyl]-4-iodo-1H-pyrazole (100.0 mg, 0.2461 mmol) in THF (6 mL, 70 mmol) was cooled to −78° C. and added 1.5 M of LDA in cyclohexane (0.213 mL, 0.320 mmol). After stirring for 5 min, DMF (0.1 mL, 1 mmol) was added slowly, and the mixture was stirred at −78° C. for 30 min. Sat. NH4Cl was added to quench, and the organic solvent was removed in vacuo. The material was extracted with DCM and water, and the organic layer was dry-loaded onto silica gel for column chromatography, eluting with 1-3% EtOAc/heptane. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a clear oil. MS (ES+): m/z=435.10 (100) [MH+]. HPLC: tR=2.18 min (polar—3 min, UPLC-ACQUITY).

Provenance & Evidence