1,4-Dioxane → 6-(2-Ethylsulfanylphenyl)-5-methyl-2-pentafluoroethylimidazo[1,2-a]pyridine

HRID 521690Notes

Reaction equation

HRID 521690 reaction equation
[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1B1OC(C)(C)C(C)(C)O1)[CH3:2].Br[C:20]1[CH:21]=[CH:22][C:23]2[N:24]([CH:27]=[C:28]([C:30]([F:36])([F:35])[C:31]([F:34])([F:33])[F:32])[N:29]=2)[C:25]=1[CH3:26].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C(OCC)(=O)C>[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:20]1[CH:21]=[CH:22][C:23]2[N:24]([CH:27]=[C:28]([C:30]([F:36])([F:35])[C:31]([F:34])([F:33])[F:32])[N:29]=2)[C:25]=1[CH3:26])[CH3:2]

Participants

8

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 1180350376-Bromo-5-methyl-2-pentafluoroethylimidazo[1,2-a]pyridineHCID 1237879692-(2-(Ethylthio)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 1182058266-(2-Ethylsulfanylphenyl)-5-methyl-2-pentafluoroethylimidazo[1,2-a]pyridineYield 103.5%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.53 g of 2-ethylsulfanylphenylboronic acid pinacol ester, 0.65 g of 6-bromo-5-methyl-2-pentafluoroethylimidazo[1,2-a]pyridine, 0.02 g of tris(dibenzylideneacetone)dipalladium(0), 0.05 g of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylphenyl, 1.0 g of tripotassium phosphate and 3 ml of 1,4-dioxane was stirred under heat-reflux for 9 hours. Ethyl acetate and water were added to the cooled reaction mixture, and the mixture was filtered. The filtrate was extracted with ethyl acetate and then dried over anhydrous sodium sulfate. The dried matter was concentrated under reduced pressure, and then the resulting residue was applied to a silica gel column chromatography to obtain 0.79 g of 6-(2-ethylsulfanylphenyl)-5-methyl-2-pentafluoroethylimidazo[1,2-a]pyridine (Compound of Present Invention 29).

Workup

  1. temperatureunder heat-reflux for 9 hours
  2. filtrationthe mixture was filtered
  3. extractionThe filtrate was extracted with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe dried matter was concentrated under reduced pressure

Sources & evidence

ORD record
ord-29399ce4611d4c53bac0336892a69715
Source dataset
uspto-grants-2016_05
Patent number
US09328121B1

Reaction notes

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