Toluene → HCID 68091055, compound

HRID 533644Notes

Reaction equation

HRID 533644 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:20]([CH3:21])[C:11]3=[N:12][CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=[C:10]3[N:9]=2)=[C:4]([S:22]([CH2:25][CH3:26])(=[O:24])=[O:23])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:32]1[N:37]=[CH:36][CH:35]=[CH:34][N:33]=1)CCC.C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:25]([S:22]([C:4]1[CH:3]=[C:2]([C:32]2[N:37]=[CH:36][CH:35]=[CH:34][N:33]=2)[CH:7]=[CH:6][C:5]=1[C:8]1[N:20]([CH3:21])[C:11]2=[N:12][CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=[C:10]2[N:9]=1)(=[O:24])=[O:23])[CH3:26]

Participants

6

Reactant 3

HCID 1140TolueneHCID 27632512-(Tributylstannyl)pyrimidine2×HCID 68091210HCID 68091210, compound

Product 1

HCID 68091055HCID 68091055, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 962WaterSolvent

Procedure

A mixture of 2-(4-bromo-2-ethylsulfonylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.20 g), 2-tributylstannylpyrimidine (0.17 g), tetrakis(triphenylphosphine)palladium (27 mg) and toluene (5 ml) was heated at reflux under nitrogen atmosphere for 5.5 hours. After the mixture was cooled to room temperature, to the mixture, 2-tributylstannylpyrimidine (0.17 g) and tetrakis(triphenylphosphine)palladium (27 mg) were added, and stirred under reflux for further 8 hours. After the mixture was cooled to room temperature, water was poured thereinto, and extracted with ethyl acetate. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.20 g of 2-[2-ethylsulfonyl-4-(pyrimidine-2-yl)-phenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, Present Compound 333).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen atmosphere for 5.5 hours
  3. additionwere added
  4. temperatureunder reflux for further 8 hours
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f6ad32022569498bb953114e5c9a2cea
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Reaction notes

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