Sodium hydride → HCID 9985392, compound

Participants

Reaction Steps

7-Trifluoromethyl-4-quinoline-thiol (300 mg, 1.3 mmol) was charged in a 50 mL round-bottomed flask equipped with a magnetic stirrer and under inert atmosphere. Anhydrous DMF (10 mL) and NaH 60% dispersion in oil (53 mg, 1.3 mmol) were successively added at 4° C. After 30 min a solution of 5-(8-bromo-octyloxy)-2-(tetrahydro-pyran-2-yloxymethyl)-4H-pyran-4-one 5 (500 mg, 1.2 mmol) in DMF (5 mL) was added at room temperature. The reaction mixture was stirred for 2 h at room temperature. The reaction mixture was poured in 150 mL of H2O, extracted with EtOAc (3×80 mL). The organic layer was washed with brine (2×20 mL), dried over MgSO4, filtered and evaporated to dryness. The crude compound was purified by column chromatography (SiO2; CH2Cl2:MeOH=95:5 to 98:2) to give 5-(8-(7-(trifluoromethyl)quinolin-4-ylthio)octyloxy)-2-((tetrahydro-2H-pyran-2-yloxy)methyl)-4H-pyran-4-one EHT 1006 (320 mg, 47% yield) as a white solid.

Provenance & Evidence