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

HRID 1750059
Notes
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Reaction equation

HRID 1750059 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH:10]=[C:5]2[N:4]=[CH:3]1.Br[C:19]1[CH:24]=[CH:23][C:22]([S:25][C:26]([F:29])([F:28])[F:27])=[CH:21][C:20]=1[S:30][CH2:31][CH3:32].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>[CH2:31]([S:30][C:20]1[CH:21]=[C:22]([S:25][C:26]([F:29])([F:27])[F:28])[CH:23]=[CH:24][C:19]=1[C:3]1[N:2]([CH3:1])[C:6]2=[N:7][CH:8]=[C:9]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH:10]=[C:5]2[N:4]=1)[CH3:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 1180352773-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridineHCID 1180355631-Bromo-2-ethylsulfanyl-4-trifluoromethylsulfanylbenzene

Product 1

HCID 1180356092-(2-ethylsulfanyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridineYield 82.4%

Reagents, catalysts & solvents 5

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

Procedure

A mixture of 0.12 g of 3-methyl-6-pentafluoroethyl-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 0.19 g of 2-(2-ethylsulfanyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine (hereinafter, referred to as Compound 8).

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-21d1dffe809c4bd296363b006f79ba2f
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09156838B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes