Imidazole → HCID 178455351, compound

Participants

Reaction Steps

A mixture of trans-4-(4-iodo-1H-pyrazol-1-yl)-cyclohexanol (1.00 g, 3.42 mmol), tert-butyldimethylsilyl chloride (1.03 g, 6.85 mmol), and DMAP (80 mg, 0.7 mmol), 1H-imidazole (699 mg, 10.3 mmol) in DCM (20 mL) was stirred RT for 20 min. The mixture was diluted with DCM and washed with saturated NaHCO3. The organic layer was dry-loaded onto silica gel. Flash chromatography (3% EtOAc:hexanes) afforded 1.37 g (98%) of the title compound as a clear oil. 1H NMR (400 MHz, DMSO-d6): δ 0.05 (s, 6 H), 0.86 (s, 9 H), 1.33-1.47 (m, 2 H), 1.70-1.91 (m, 4 H), 1.96 (d, J=11.9 Hz, 2 H), 3.58-3.75 (m, 1 H), 4.11-4.21 (m, 1 H), 7.49 (s, 1 H), 7.92 (s, 1 H); MS (ESI): 407.05 [M+H]+; HPLC tR=3.22 min.

Provenance & Evidence