Lawesson's reagent → HCID 18416160, compound

Participants

Reaction Steps

A mixture of 7-isopropoxy-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinolin-2(3H)-one (EXAMPLE 22) (48.4 mg, 0.119 mmol) and Lawesson's reagent (0.144 g, 0.356 mmol) in 2.4 mL toluene was heated at reflux for 6 h, whereupon the mixture was partitioned between EtOAc (40 mL) and water (20 mL). The aqueous layer was extracted with EtOAc (20 mL), and the combined organic layers were washed with brine (20 mL), dried over MgSO4, filtered, and concentrated. Flash chromatography (9:1 hexanes:EtOAc) afforded 41 mg of 7-isopropoxy-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinolin-2(3H)-thione, a yellow oil. Data for 7-isopropoxy-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinolin-2 (3H)-thione: Rf 0.36 (9:1 hexanes:EtOAc); 1H NMR (400 MHz, CDCl3) δ 7.72 (broad s, 1H), 7.48 (s, 1H), 7.13 (s, 1H), 5.54 (hept, 1H, J=6.2), 5.32-5.42 (m, 2H), 5.05 (s, 2H), 1.41 (d, 6H, J=6.2).

Provenance & Evidence