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

반응식

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=O.[CH3:18][S:19]([CH2:22][C:23](=O)[CH3:24])(=[O:21])=[O:20].[Na]>CC(O)C>[Br:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[N:1]=[C:23]([CH3:24])[C:22]([S:19]([CH3:18])(=[O:21])=[O:20])=[C:9]2[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1

참가 물질

실험 절차

(2-Amino-5-bromo-phenyl)-(4-fluoro-phenyl)-methanone (compound of example A.1) (4 g, 14 mmol), methanesulfonylacetone (2.78 g, 20 mmol) and sodium tetrachloroaureate(III) dihydrate (0.27 g, 0.7 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 NaCl (1×). The crude product was purified by chromatography in heptane/ethyl acetate with a gradient from 100:0 to 70:30. One obtained a light brown solid (1.5 g, 28%). MS: m/z=394 (M).