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

Temperature

25 °C

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).

1. custompartitioned between dichloromethane (400 mL) and water (400 mL)
2. customThe organic layer was separated
3. extractionthe aqueous layer was extracted with additional dichloromethane (200 mL)
4. dry with materialThe combined organic extracts were dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD record

ord-ceafd9b22cc747369880d343e9111e9d

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07842685B2