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Methyl iodide → Methyl 3-methyl-6-[(1-methylethyl)thio]-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

HRID 245190
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HRID 245190 반응식
[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].[CH3:30][CH:31]([S-:33])[CH3:32].[Na+].I[CH3:36]>CS(C)=O.O>[CH3:26][C:8]1[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:23])[F:25])[CH:17]=2)=[N:10][C:11]2[C:6]([C:7]=1[C:27]([O:29][CH3:36])=[O:28])=[CH:5][C:4]([S:33][CH:31]([CH3:32])[CH3:30])=[C:13]([O:14][CH3:15])[CH:12]=2
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참가 물질

7

반응물 4

HCID 6328Methyl iodideHCID 24758Sodium hydride2회HCID 3470666Sodium 2-propanethiolate2회HCID 673840026-Fluoro-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

생성물 1

HCID 67383440Methyl 3-methyl-6-[(1-methylethyl)thio]-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate수율 58%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

Sodium hydride (1.265 g, 31.6 mmol) was added 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), and the mixture was stirred for 20 min. Sodium 2-propanethiolate (2.53 g, 23.20 mmol) was added, and the resulting mixture was stirred at 100° C. overnight. The mixture was cooled to room temperature, treated with NaH (1.27 g of 60% dispersion in mineral oil, 31.6 mmol) and sodium 2-propanethiolate (2.53 g, 23.20 mmol), and heated at 100° C. for an additional 4 hours. The reaction mixture was cooled to room temperature. Iodomethane (3.96 mL, 63.3 mmol) was added, and the mixture was stirred for 2 hours. The mixture was diluted with water and extracted with methylene chloride (three times). The combined organic extracts were washed with brine, 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 3-methyl-6-[(1-methylethyl)thio]-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (5.5 g, 58% yield). This material was used in the next step without further purification. MS (m/z) 450.1 (M+H+).

후처리

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

출처 및 근거

ORD 기록
ord-73a1ba9ac68c4cb980431d3e058346ae
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08658636B2

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