4-Bromotoluene → 5-(Benzyloxy)-3-p-tolyl-3H-imidazo[4,5-b]pyridine

HRID 1890343Notes

Reaction equation

HRID 1890343 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]2[NH:15][CH:16]=[N:17][C:12]2=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].C(OC1N=C2N=CN(C3C=CC(C)=CC=3)C2=CC=1)C1C=CC=CC=1>CCOC(C)=O.[Cu]I.CN1C(=O)CCC1>[CH2:1]([O:8][C:9]1[N:14]=[C:13]2[N:15]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[CH:16]=[N:17][C:12]2=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 78054-BromotolueneHCID 11430Potassium CarbonateHCID 673139335-(benzyloxy)-1-p-tolyl-1H-imidazo[4,5-b]pyridineHCID 178420377HCID 178420377, compound

Product 1

HCID 673118605-(Benzyloxy)-3-p-tolyl-3H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

5-(Benzyloxy)-3H-imidazo[4,5-b]pyridine (0.204 g, 0.906 mmol), 4-bromotoluene (0.123 mL, 0.996 mmol), potassium carbonate (263 mg, 1.90 mmol), copper(1) iodide (8.6 mg, 0.045 mmol) and NMP (3 mL) were heated at 210° C. for 1 h under microwave irradiation in a heavy walled sealed tube. The mixture was cooled to room temperature and diluted with EtOAc. The solution was washed with water and the organics were dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography to give a mixture of the title compound and its regioisomer 5-(benzyloxy)-1-p-tolyl-1H-imidazo[4,5-b]pyridine (154 mg). LCMS m/z=316.3 [M+H]+.

Workup

  1. washThe solution was washed with water
  2. dry with materialthe organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography
  6. customto give

Sources & evidence

ORD record
ord-b840706e0710458a8b41e377659c3ad1
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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