Cesium carbonate → HCID 17975832, compound

7-Trifluoromethyl-4-quinolinol (320 mg, 1.5 mmol), Cs2CO3 (500 mg, 1.5 mmol) and anhydrous DMF (3 mL) were stirred at 70° C. in a 50 ml round-bottomed flask equipped with a magnetic stirrer. After 20 min, 5-(5-bromopentyloxy)-2-(hydroxymethyl)-4H-pyran-4-one 10 (420 mg, 1.4 mmol) in DMF (2 mL) was added and the reaction mixture was stirred for 15 h at 75° C. DMF was evaporated at 60° C. and the reaction mixture was poured in 20 mL of H2O and extracted with EtOAc (3×100 mL). The organic layer was washed with brine (10 mL), dried over MgSO4, filtered and evaporated to dryness. The crude compound was purified by column chromatography (SiO2; CH2Cl2:MeOH=98:2 to 90:10) to give after evaporation 5-(5-(7-(trifluoromethyl)quinolin-4-yloxy)pentyloxy)-2-(hydroxymethyl)-4H-pyran-4-one 12 (300 mg, 47% yield) as a white solid.

1. customequipped with a magnetic stirrer
2. customDMF was evaporated at 60° C.
3. additionthe reaction mixture was poured in 20 mL of H2O
4. extractionextracted with EtOAc (3×100 mL)
5. washThe organic layer was washed with brine (10 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customevaporated to dryness
9. customThe crude compound was purified by column chromatography (SiO2; CH2Cl2:MeOH=98:2 to 90:10)
10. customto give

ORD record

ord-84c1840a2ab34905b1dcd79c11dac3cf

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07514432B2