1-Methylimidazole → HCID 25172143, compound

HRID 1506656Notes

Reaction equation

HRID 1506656 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH3:9][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[H+].[B-](F)(F)(F)F.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:14]2[N:10]([CH3:9])[CH:11]=[N:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 13901-MethylimidazoleHCID 10796Cesium carbonateHCID 125101-Chloro-4-iodobenzeneHCID 28118Tetrafluoroboric acidHCID 75806Tricyclohexylphosphine

Product 1

HCID 25172143HCID 25172143, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

1-Chloro-4-iodobenzene (10 g, 42 mmol) was combined with 1-methyl-1H-imidazole (13.3 mL, 168 mmol), Pd(OAc)2 (470 mg), PCy3.HBF4 (1.54 g), Cs2CO3 (13.7 g, 42 mmol) in DMF (200 mL). The reaction was heated to 120° C. for 15 hr. After cooling to ambient temperature, the reaction was filtered to remove solids and the eluent was partitioned between EtOAc and H2O. The organics were separated, washed with saturated aqueous NaHCO3, and dried with saturated aqueous NaCl. Solvents were removed in vacuo and the residue purified by column chromatography on silica to provide the desired product. MS (m/z) 193.3 [M+H]+.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. filtrationthe reaction was filtered
  3. customto remove solids
  4. customthe eluent was partitioned between EtOAc and H2O
  5. customThe organics were separated
  6. washwashed with saturated aqueous NaHCO3
  7. dry with materialdried with saturated aqueous NaCl
  8. customSolvents were removed in vacuo
  9. customthe residue purified by column chromatography on silica

Sources & evidence

ORD record
ord-332b86e57f93482aafa221c884dcbd2e
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Reaction notes

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