Water → HCID 17975828, compound

In a 25 mL round-bottomed flask 7-trifluoromethyl-quinoline-4-thiol (1.0 g, 4.37 mmol) was dissolved in 10 mL DMF anhydrous and NaH (60% dispersion in oil, 184 mg) was added slowly. The reaction was stirred at RT for 10 min. In a 50 mL round-bottomed flask 1,4-bis-bromomethyl-benzene (1.27 g, 4.80 mmol) was dissolved in DMF anhydrous (10 mL) and the solution was stirred at 0° C. for 10 min. The first solution was added via syringe to this solution and the reaction was stirred at 0° C. for 15 min. The solution orange became pale yellow and the mixture stirred 1.25 h at RT. Water (50 mL) was added and the product extracted with diethyl ether (5×100 mL). The organic layer was washed with water (3×50 mL), brine (3×50 mL), dried with MgSO4, filtered and evaporated. The crude product was purified by column chromatography on silica using as eluent cyclohexane:diethyl ether=7:3. 4-(2-(Bromomethyl)benzylthio)-7-(trifluoromethyl)quinoline 27 was obtained (205 mg, 12% yield) as white solid.

1. stirringthe solution was stirred at 0° C. for 10 min
2. additionThe first solution was added via syringe to this solution
3. stirringthe reaction was stirred at 0° C. for 15 min
4. stirringthe mixture stirred 1.25 h at RT
5. extractionthe product extracted with diethyl ether (5×100 mL)
6. washThe organic layer was washed with water (3×50 mL), brine (3×50 mL)
7. dry with materialdried with MgSO4
8. filtrationfiltered
9. customevaporated
10. customThe crude product was purified by column chromatography on silica using as eluent cyclohexane

ORD record

ord-1ace76aaa4a6499bb240b078d16d1931

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07514432B2