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

HRID 245240Notes

Reaction equation

HRID 245240 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-3739e16ef493444eb60dde118a4240d1
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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