Methyl iodide → Methyl 6-(ethylthio)-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

HRID 245160

反応式

HRID 245160 の反応式
[H-].[Na+].F[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=1)[C:8]([CH3:26])=[C:7]2[C:27]([OH:29])=[O:28].[CH2:30]([S-:32])[CH3:31].[Na+].I[CH3:35]>CS(C)=O.O>[CH2:30]([S:32][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:25])[F:23])[CH:17]=1)[C:8]([CH3:26])=[C:7]2[C:27]([O:29][CH3:35])=[O:28])[CH3:31]

参加物

7

反応物 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 4459711Sodium ethanethiolateHCID 673840026-Fluoro-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

生成物 1

HCID 67418873Methyl 6-(ethylthio)-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate収率 77%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

Sodium hydride (1.27 g, 31.6 mmol) was added portionwise to a suspension of 6-fluoro-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (8.0 g, 21.09 mmol) in dimethyl sulfoxide (50 mL). The mixture was stirred for 20 min. Sodium ethanethiolate (2.168 g, 23.20 mmol) was added and the resulting mixture was stirred at 100° C. for 1 h. The mixture was cooled to room temperature, iodomethane (3.96 mL, 63.3 mmol) was added, and the mixture was stirred for 2 h. The reaction mixture was diluted with water and extracted three times with methylene chloride. The combined organic extracts were washed with brine (two times), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via column chromatography (ISCO, 330 g silica, 0-10% ethyl acetate/methylene chloride) to afford methyl 6-(ethylthio)-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (7.05 g, 77% yield, about 70% pure). MS (m/z) 436.1 (M+H+).

後処理

  1. stirringthe resulting mixture was stirred at 100° C. for 1 h
  2. stirringthe mixture was stirred for 2 h
  3. extractionextracted three times with methylene chloride
  4. washThe combined organic extracts were washed with brine (two times)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified via column chromatography (ISCO, 330 g silica, 0-10% ethyl acetate/methylene chloride)

出典と根拠

ORDレコード
ord-9db37b39a1b7445b96939482cc9612ad
出典データセット
uspto-grants-2014_02
特許番号
US08658636B2

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