Imidazole → 1H-Pyrazole, 1-[trans-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]cyclohexyl]-4-iodo-

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Reaction Steps

A mixture of trans-4-(4-Iodo-pyrazol-1-yl)-cyclohexanol (Compound 137 D, 1.00 g, 3.42 mmol), tert-butyldimethylsilyl chloride (1.03 g, 6.85 mmol), 4-dimethylaminopyridine (80 mg, 0.7 mmol), 1H-imidazole (699 mg, 10.3 mmol) and DCM (20 mL, 300 mmol) was stirred room temperature for 20 min. The material was transferred to a separatory funnel, extracting with DCM and sat. NaHCO3. The organic layer was dry-loaded onto silica gel for column chromatography, eluting with 3% EtOAc/hexanes. The fractions containing the pure product were concentrated in vacuo to afford the title compound as 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 (ES+): m/z=407.05 [MH+]. HPLC: tR=3.22 min (polar—5 min, ZQ3).

Provenance & Evidence