Water → HCID 59334594, compound

HRID 1639823Notes

Reaction equation

HRID 1639823 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[F:9][C:10]([F:28])([F:27])[C:11]1[N:12]=[C:13]2[CH:18]=[CH:17][CH:16]=[C:15](/[CH:19]=[CH:20]/[C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:14]2[CH:26]=1.O>CS(C)=O>[F:28][C:10]([F:9])([F:27])[C:11]1[N:12]=[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]3[CH2:4][CH:20]3[C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:14]2[CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 66720629Ethyl (2E)-3-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-5-yl]-2-propenoate

Product 1

HCID 59334594HCID 59334594, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a suspension of 60% sodium hydride (1.24, 28.5 mmol) in dimethyl sulfoxide (50 mL) was added trimethylsulfoxonium iodide (6.26 g, 28.5 mmol) at 0° C., and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added a solution of ethyl (2E)-3-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-5-yl]acrylate (6.74 g, 23.7 mmol) in dimethyl sulfoxide (100 mL) at 0° C., and the mixture was stirred at room temperature for 4 hr. Water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=33/67) to give the title compound (3.40 g, yield 48%).

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=33/67)

Sources & evidence

ORD record
ord-9cb13d1fe85e4d5098ebd296123fd843
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

Loading…