Methyl iodide → HCID 178497883, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the title compound from Example 13 Step E (234 mg, 0.942 mmol) in DCM (4.7 mL) were added 2,6-di-tert-butylpyridine (0.318 mL, 1.41 mmol) and silver trifluoromethanesulfonate (266 mg, 1.04 mmol). The resulting solution was cooled to 0° C., and iodomethane (0.071 mL, 1.13 mmol) was added. After 30 min, the reaction mixture was allowed to warm to ambient temperature and was held at this temperature for 3 h, whereupon it was filtered through Celite, rinsing with DCM. The reaction mixture was concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 30% EtOAc in hexanes, then 30 to 100% EtOAc in hexanes) provided the title compound. Analytical data for the major isomer (trans cyclohexyl): LCMS m/z 263.17 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 7.85 (d, J=8.5 Hz, 1H), 7.08-7.06 (m, 2H), 3.86 (s, 3H), 3.38 (s, 3H), 3.24-3.17 (m, 1H), 2.58 (s, 3H), 2.49 (dt, J=12.0, 3.5 Hz, 1H), 2.21-2.18 (m, 2H), 1.94-1.92 (m, 2H), 1.54-1.46 (m, 2H), 1.39-1.30 (m, 2H).

Provenance & Evidence