Methyl iodide → HCID 67383868, compound

HRID 245214Notes

Reaction equation

HRID 245214 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([C:25]([O:27][CH3:28])=[O:26])=[C:9]([CH3:24])[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)=[N:11]2)=[CH:6][C:5]=1F)[CH3:2].[CH2:30]([S-:32])[CH3:31].[Na+].IC>CS(C)=O.O>[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([C:25]([O:27][CH3:28])=[O:26])=[C:9]([CH3:24])[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:22])([F:21])[F:23])[CH:15]=3)=[N:11]2)=[CH:6][C:5]=1[S:32][CH2:30][CH3:31])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 4459711Sodium ethanethiolateHCID 67383776HCID 67383776, compound

Product 1

HCID 67383868HCID 67383868, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 7-(ethyloxy)-6-fluoro-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (9.35 g, 22.95 mmol) in dimethyl sulfoxide (150 mL) was added sodium ethanethiolate (6.44 g, 68.9 mmol) and the resulting mixture was stirred at room temperature overnight. Iodomethane (7.18 mL, 115 mmol) was added, and the mixture was stirred for 2 h. The mixture was diluted with water and extracted with methylene chloride. The organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to afford methyl 7-(ethyloxy)-6-(ethylthio)-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate. This material was used without further purification. MS (m/z) 450.1 (M+H+).

Workup

  1. stirringthe mixture was stirred for 2 h
  2. extractionextracted with methylene chloride
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e3ada61207a84f969e35b4c23d45e15a
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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