1-(Methylsulphonyl)acetone → 6-Bromo-4-(4-chloro-phenyl)-3-methanesulfonyl-2-methyl-quinoline

Participants

Reaction Steps

(2-Amino-5-bromo-phenyl)-(4-chloro-phenyl)-methanone (compound of example A.2) (4 g, 12.9 mmol), methanesulfonylacetone (2.63 g, 19.3 mmol) and sodium tetrachloroaureate(III) dihydrate (0.26 g, 0.64 mmol) were heated at reflux in 2-propanol (50 ml) for 4 days. The resulting mixture was evaporated to dryness and the residue extracted with dichloromethane (2×), 1 N NaOH (2×) and sat. NaCl (1×). The crude product was purified by chromatography on silica gel in dichloromethane. The product was crystallized from dichloromethane/heptane by evaporation of dichloromethane. One obtained a light yellow solid (1 g, 19%). MS: m/z=410 (M).

Provenance & Evidence