Sulfoxonium, trimethyl-, iodide (1:1) → 5-(1-Phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-carboxylic acid

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Reaction Conditions

Reaction Steps

Potassium 2-methylpropan-2-olate (0.66 g, 5.9 mmol) was dissolved in anhydrous DMSO (19.5 mL) under argon. Trimethylsulfoxonium iodide (1.3 g, 5.9 mmol) was added to the resulting solution in one portion. After 10 min, this dissolved, and the resulting clear solution was added via cannula (over ˜2 min) to a suspension of sodium 5-(1-phenylvinyl)thiazolo[5,4-b]pyridine-2-carboxylate (1.19 g, 3.9 mmol) in DMSO (5 mL) at 25° C. The resulting solution was stirred at 25° C. for 1 h. The reaction solution was then diluted with 1.0N HCl (8.0 mL) and partitioned between dichloromethane (400 mL) and water (400 mL). The organic layer was separated, and the aqueous layer was extracted with additional dichloromethane (200 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to afford crude 5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-carboxylic acid as a yellow oil. MS (ESI) m/z: Calculated: 296.1; Observed: 297.0 (M++1).

Provenance & Evidence