Potassium Carbonate → HCID 71294070, compound

Participants

Reaction Conditions

Reaction Steps

In DMSO (3.0 mL) was dissolved 1-(5-bromopyridin-3-yl)-2,2,2-trifluoroethyl acetate (429 mg, 1.44 mmol) obtained in Step 3. To the solution were added sodium methanesulfinate (176 mg, 1.73 mmol), copper iodide (I) (41.1 mg, 0.216 mmol), L-proline (49.7 mg, 0.432 mmol) and sodium bicarbonate (36.3 mg, 0.432 mg) and the mixture was stirred at 95° C. for 72 hours. Water was added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure and the residue was dissolved in methanol (10.0 mL). Potassium carbonate (597 mg, 4.32 mmol) was added and the mixture was stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure and water was added. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/7) to give 2,2,2-trifluoro-1-(5-(methylsulfonyl)pyridin-3-yl)ethanol (61.4 mg, 17% yield).

Provenance & Evidence