Sulfoxonium, trimethyl-, iodide (1:1) → Methyl 1-((3-fluoro-4-(5-(1-(4-fluorophenyl)-cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylate

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Reaction Steps

To a solution of potassium tert-butoxide (0.080 g, 0.71 mmol) and trimethylsulfoxonium iodide (0.16 g, 0.71 mmol) in 2 mL DMSO was added slowly dropwise a solution of methyl 1-((3-fluoro-4-(5-(1-(4-fluorophenyl)vinyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylate (0.170 g, 0.36 mmol) in 2 mL THF, with 1 mL rinse. The solution became colored. After 30 min, the reaction mixture was quenched with sat'd aq. NH4Cl and EtOAc. The organic layer was washed with water, then brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The material was treated with DCM and adsorbed onto 1.5 g silica gel and passed through a Redi-Sep® pre-packed silica gel column (12 g) using 0-100% EtOAc/hexane. The product-containing fractions were concentrated to afford methyl 1-((3-fluoro-4-(5-(1-(4-fluorophenyl)-cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylate as a yellow solid. MS (ESI) m/z: calculated: 491.2; Observed: 492.1 (M++1).

Provenance & Evidence