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

HRID 13673

反応式

HRID 13673 の反応式
[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]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1)=O.[CH3:21][S:22]([CH2:25][C:26](=O)[CH3:27])(=[O:24])=[O:23].[Na]>C(O)C>[Br:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[N:1]=[C:26]([CH3:27])[C:25]([S:22]([CH3:21])(=[O:24])=[O:23])=[C:9]2[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1

参加物

5

反応物 3

HCID 786951-(Methylsulphonyl)acetoneHCID 5360545SodiumHCID 12001533(2-Amino-5-bromo-phenyl)-(4-trifluoromethyl-phenyl)-methanone

生成物 1

HCID 120017256-Bromo-3-methanesulfonyl-2-methyl-4-(4-trifluoromethyl-phenyl)-quinoline収率 29.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

(2-Amino-5-bromo-phenyl)-(4-trifluoromethyl-phenyl)-methanone (compound of example A.3) (4 g, 11.6 mmol), methanesulfonylacetone (2.37 g, 17.4 mmol) and sodium tetrachloroaureate(III) dihydrate (0.23 g, 0.58 mmol) were heated at reflux in ethanol (50 ml) for 4 days. The resulting mixture was evaporated to dryness and the residue extracted with dichloromethane (2×), NaOH (2×) and NaCl (1×). The crude product was purified by chromatography on silica gel in heptane/ethyl acetate 70:30. One obtained a light yellow solid (1.5 g, 29%). MS: m/z=444 (M).

後処理

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

出典と根拠

ORDレコード
ord-7da5d5e5e52a4a668d4398aaa7b5faaa
出典データセット
uspto-grants-2010_06
特許番号
US07728142B2

関連ノート

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