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

HRID 521687Notes

Reaction equation

HRID 521687 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:33])([F:32])[F:31])[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:31])([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 1154037216-Bromo-5-methyl-2-trifluoromethylimidazo[1,2-a]pyridineHCID 1237879692-(2-(Ethylthio)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 1182058326-(2-Ethylsulfanylphenyl)-5-methyl-2-trifluoromethylimidazo [1,2-a]pyridineYield 24.2%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.52 g of 2-ethylsulfanylphenylboronic acid pinacol ester, 0.56 g of 6-bromo-5-methyl-2-trifluoromethylimidazo[1,2-a]pyridine, 0.02 g of tris(dibenzylideneacetone)dipalladium(0), 0.05 g of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylphenyl, 0.84 g of tripotassium phosphate and 6 ml of 1,4-dioxane was stirred under heat-reflux for 3 hours. 0.1 ml of water was added to the cooled reaction mixture, and the mixture was stirred under heat-reflux for 5 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 0.16 g of 6-(2-ethylsulfanylphenyl)-5-methyl-2-trifluoromethylimidazo[1,2-a]pyridine (Compound of Present Invention 28).

Workup

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

Sources & evidence

ORD record
ord-3441649a0f094a9fad018bcef867982f
Source dataset
uspto-grants-2016_05
Patent number
US09328121B1

Reaction notes

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