Toluene → 2-(2-ethylsulfanyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine

HRID 1750055Notes

Reaction equation

HRID 1750055 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([S:11][C:12]([F:15])([F:14])[F:13])[CH:10]=[C:5]2[N:4]=[CH:3]1.Br[C:17]1[CH:22]=[CH:21][C:20]([S:23][C:24]([F:27])([F:26])[F:25])=[CH:19][C:18]=1[S:28][CH2:29][CH3:30].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C(OCC)(=O)C>[CH2:29]([S:28][C:18]1[CH:19]=[C:20]([S:23][C:24]([F:27])([F:25])[F:26])[CH:21]=[CH:22][C:17]=1[C:3]1[N:2]([CH3:1])[C:6]2=[N:7][CH:8]=[C:9]([S:11][C:12]([F:13])([F:15])[F:14])[CH:10]=[C:5]2[N:4]=1)[CH3:30]

Participants

10

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 1180355631-Bromo-2-ethylsulfanyl-4-trifluoromethylsulfanylbenzeneHCID 1180355783-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 1180356112-(2-ethylsulfanyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridineYield 90.3%

Reagents, catalysts & solvents 5

HCID 11776TriphenylphosphineCatalystHCID 165397Cupric acetate monohydrateCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.11 g of 3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine, 0.15 g of 1-bromo-2-ethylsulfanyl-4-trifluoromethylsulfanylbenzene, 0.01 g of palladium(II) acetate, 0.01 g of triphenylphosphine, 0.02 g of copper(II) acetate monohydrate, 0.13 g of potassium carbonate and 3 ml of toluene was stirred under heating and refluxing for 2 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 0.20 g of 2-(2-ethylsulfanyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine (hereinafter, referred to as Compound 7).

Workup

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

Sources & evidence

ORD record
ord-f86d8bbd09d64d1f88924f79388f1c15
Source dataset
uspto-grants-2015_10
Patent number
US09156838B2

Reaction notes

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