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

HRID 13667

Reaktionsgleichung

Reaktionsgleichung von HRID 13667
[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

Komponenten

5

Edukt 3

HCID 786951-(Methylsulphonyl)acetoneHCID 1359860(2-Amino-5-bromophenyl)(4-fluorophenyl)methanoneHCID 5360545Sodium

Produkt 1

HCID 120017196-Bromo-4-(4-fluoro-phenyl)-3-methanesulfonyl-2-methyl-quinolineAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

(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).

Aufarbeitung

  1. customThe resulting mixture was evaporated to dryness
  2. extractionthe residue extracted with dichloromethane (2×), 1 N NaOH (2×) and NaCl (1×)
  3. customThe crude product was purified by chromatography in heptane/ethyl acetate with a gradient from 100:0 to 70:30

Quellen und Nachweise

ORD-Eintrag
ord-b053d5718d664bb6a9c72f5df8209328
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728142B2

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