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

HRID 13669

Reaktionsgleichung

Reaktionsgleichung von HRID 13669
[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]([Cl: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]([Cl:17])=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 786951-(Methylsulphonyl)acetoneHCID 182477(2-Amino-5-bromophenyl)(4-chlorophenyl)methanoneHCID 5360545Sodium

Produkt 1

HCID 120017216-Bromo-4-(4-chloro-phenyl)-3-methanesulfonyl-2-methyl-quinolineAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

(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).

Aufarbeitung

  1. customThe resulting mixture was evaporated to dryness
  2. extractionthe residue extracted with dichloromethane (2×), 1 N NaOH (2×) and sat. NaCl (1×)
  3. customThe crude product was purified by chromatography on silica gel in dichloromethane
  4. customThe product was crystallized from dichloromethane/heptane by evaporation of dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-2e6422c6666e4cd8adb388d13ca64956
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728142B2

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