Dimethyl Sulfoxide → Methyl 6-bromo-3-methyl-2-[4-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

HRID 245240ノート

反応式

HRID 245240 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)[C:6]([CH3:22])=[C:5]2[C:23]([OH:25])=[O:24].[CH3:26]S(C)=O.CI.C(=O)([O-])[O-].[Cs+].[Cs+]>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:13]=[CH:14][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:16][CH:17]=1)[C:6]([CH3:22])=[C:5]2[C:23]([O:25][CH3:26])=[O:24]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 673836206-Bromo-3-methyl-2-[4-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

生成物 1

HCID 67384046Methyl 6-bromo-3-methyl-2-[4-(trifluoromethyl)phenyl]-4-quinolinecarboxylate収率 98%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

6-Bromo-3-methyl-2-[4-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (15.6 g, 38.0 mmol), dimethyl sulfoxide (DMSO) (190 ml), methyl iodide (4.76 mL, 76 mmol) and cesium carbonate (12.39 g, 38.0 mmol) were added to a 500 mL flask The mixture was stirred at RT for 2 h. Water (200 mL) was added to the resulting slurry, and the mixture was stirred for 10 min, the solid was collected by filtration, and the filter cake was washed with 500 mL of water. The resulting solid was dried under reduced pressure to afford the desired product as a tan solid (15.75 g, 98%). MS (m/z) 426.0 (M+H+).

後処理

  1. stirringthe mixture was stirred for 10 min
  2. filtrationthe solid was collected by filtration
  3. washthe filter cake was washed with 500 mL of water
  4. customThe resulting solid was dried under reduced pressure

出典と根拠

ORDレコード
ord-3739e16ef493444eb60dde118a4240d1
出典データセット
uspto-grants-2014_02
特許番号
US08658636B2

反応ノート

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