(Diethylamino)sulfur trifluoride → HCID 10252738, compound

Participants

Reaction Conditions

Reaction Steps

2-Hydroxymethyl-5-[5-(7-trifluoromethyl-quinolin-4-ylsulfanyl)-pentyloxy]-pyran-4-one EHT 5909 (100 mg, 0.23 mmol) was dissolved in dichloromethane (5 mL). The mixture was stirred at 0° C. for 15 min. Diethylaminosulfur trifluoride (DAST, 33 μL, 0.25 mmol) was added via syringe. The mixture was stirred at room temperature for 10 min. The solution was evaporated. The crude product was purified by flash chromatography on silica using as eluent CH2Cl2:MeOH=99:01. 5-(5-(7-(Trifluoromethyl)quinolin-4-ylthio)pentyloxy)-2-(fluoromethyl)-4H-pyran-4-one EHT 8817 was obtained (48 mg, 35% yield) as a white solid.

Provenance & Evidence