Sulfoxonium, trimethyl-, iodide (1:1) → 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-cyclohexylcyclopropyl)thiazolo[5,4-b]pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of trimethylsulfoxonium iodide (0.385 g, 1.75 mmol) and potassium tert-butoxide (0.196 g, 1.75 mmol) in 4 mL DMSO was added 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-cyclohexylvinyl)thiazolo[5,4-b]pyridine (0.371 g, 0.874 mmol) rapidly as a solution in THF (8 mL min volume). The reaction mixture became a light purple color. The reaction was sealed and heated to 60° C. After 4 h, the reaction mixture was cooled, quenched with ice and sat'd aq. NH4Cl, diluted with EtOAc and the organic layer was washed with water, brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting orange oil/solid was purified by silica gel chromatography 40 g, 0-40% EA/hexanes to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-cyclohexylcyclopropyl)thiazolo[5,4-b]pyridine as a white solid. MS (ESI) m/z: calculated: 438.2; Observed: 439.1 (M++1).

Provenance & Evidence