Sulfoxonium, trimethyl-, iodide (1:1) → HCID 118235473, compound

Participants

Reaction Conditions

Reaction Steps

A solution of trimethylsulfoxonium iodide (176 mg, 0.79 mmol) and potassium tert-butoxide (85 mg, 0.75 mmol) in DMSO (2 mL) was stirred at 50° C. for 45 minutes. A solution of methyl 4-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]cyclohex-3-ene-1-carboxylate (prepared in an analogous manner to that described for Example 39, 100 mg, 0.2 mmol) in DMSO (2 mL) was added and the mixture was stirred at 50° C. for 4 h, then at room temperature for 3 days. The reaction mixture was diluted with DCM (10 mL) and washed with water (3×3 mL). The aqueous washes were combined and further extracted with DCM (2×3 mL). The organic extracts were combined, dried over sodium sulfate and evaporated. The resulting crude brown residue was diluted with DCM (3 mL) and washed with 1N aqueous NaOH solution (3×1 mL). The organic phase was dried over sodium sulfate and evaporated. The resulting pale brown residue was purified by preparative TLC, eluting with 1% MeOH in DCM, to afford the title compound (38.3 mg, 37%) as an off-white solid. Method B HPLC-MS: MH+ m/z 519, RT 1.80 minutes.

Provenance & Evidence