Dimethyl Sulfoxide → Methyl 6-bromo-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

HRID 245150ノート

反応式

HRID 245150 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1)[C:6]([CH3:24])=[C:5]2[C:25]([OH:27])=[O:26].[CH3:28]S(C)=O.C(=O)([O-])[O-].[Cs+].[Cs+].CI>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[CH:15]=1)[C:6]([CH3:24])=[C:5]2[C:25]([O:27][CH3:28])=[O:26]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 673838286-Bromo-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

生成物 1

HCID 67384067Methyl 6-bromo-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate収率 85%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a 2 L flask was added 6-bromo-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (82.5 g, 187 mmol), DMSO (1249 mL), cesium carbonate (67.2 g, 206 mmol) and methyl iodide (23.44 ml, 375 mmol). The mixture was stirred at room temperature for 2 h. To the resulting slurry was added water (500 mL). The mixture became warm and was cooled with an ice/water bath. Stirring was continued an additional 30 min, then filtered and washed with H2O (2 L). The resulting solid was dried under reduced pressure then azeotroped with toluene two times to afford methyl 6-bromo-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (72.3 g, 85% yield) as a tan solid. MS (m/z) 456 (M+H+).

後処理

  1. temperatureThe mixture became warm
  2. temperaturewas cooled with an ice/water bath
  3. stirringStirring
  4. waitwas continued an additional 30 min
  5. filtrationfiltered
  6. washwashed with H2O (2 L)
  7. customThe resulting solid was dried under reduced pressure
  8. customthen azeotroped with toluene two times

出典と根拠

ORDレコード
ord-b1f5880905da46a785d4ee4bddab0755
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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