1,4-Dioxane → HCID 118205817, compound

HRID 521696Notes

Reaction equation

HRID 521696 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:25]=[CH:24][N:23]2[CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[N:28]=[C:22]2[CH:21]=1.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:25]=[CH:24][N:23]2[CH:26]=[C:27]([C:29]([F:31])([F:32])[F:30])[N:28]=[C:22]2[CH:21]=1)[CH3:2]

Participants

8

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 682947471206978-90-6HCID 1237879692-(2-(Ethylthio)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 118205817HCID 118205817, compoundYield 63.2%

Reagents, catalysts & solvents 3

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

Procedure

A mixture of 0.53 g of 2-ethylsulfanylphenylboronic acid pinacol ester, 0.52 g of 7-bromo-2-trifluoromethylimidazo[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 6 ml of 1,4-dioxane was stirred under heat-reflux for 6 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 mixture was concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 0.40 g of 7-(2-ethylsulfanylphenyl)-2-trifluoromethylimidazol[1,2-a]pyridine (Compound of Present Invention 37).

Workup

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

Sources & evidence

ORD record
ord-17cedd92a6c440e99af302e7f93dbdad
Source dataset
uspto-grants-2016_05
Patent number
US09328121B1

Reaction notes

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