HCID 67528005, compound → HCID 178505685, compound

HRID 1512176Notes

Reaction equation

HRID 1512176 reaction equation
[CH:1]1([CH:7]=[CH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=3[C:25]([F:28])([F:27])[F:26])=[CH:14][C:13]=2[N+:29]([O-])=O)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CCO.CC(O)=O.[Fe]>[CH:1]1([CH:7]=[CH:8][C:9]2[NH:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]4[C:19]([C:25]([F:28])([F:27])[F:26])=[CH:20][CH:21]=[CH:22][C:23]=4[F:24])=[CH:14][C:13]=3[N:29]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 67528005HCID 67528005, compound

Product 1

HCID 178505685HCID 178505685, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 3-cyclohexyl-N-(6′-fluoro-3-nitro-2′-trifluoromethyl-biphenyl-4-yl)-acrylamide (135 mg, 0.309 mmol, prepared as in STEP B above) in EtOH (4 mL) and HOAc (2 mL) was added Fe powder (86.3 mg, 1.54 mmol). The resulting mixture was heated at reflux overnight. The resulting mixture was allowed to cool to room temperature and filtered. The filtrate was concentrated. The residue was dissolved in DCM with heating and sonication. The DCM layer was washed with 10 mL saturated aqueous NaHCO3, separated, dried over Na2SO4 and concentrated. The residue obtained was purified on silica (EtOAc/hexane, 0:100 to 100:0, v/v) to yield 2-(2-Cyclohexyl-vinyl)-5-(2-fluoro-6-trifluoromethyl-phenyl)-1H-benzimidazole.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux overnight
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. dissolutionThe residue was dissolved in DCM
  6. temperaturewith heating
  7. customsonication
  8. washThe DCM layer was washed with 10 mL saturated aqueous NaHCO3
  9. customseparated
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated
  12. customThe residue obtained
  13. customwas purified on silica (EtOAc/hexane, 0:100 to 100:0

Sources & evidence

ORD record
ord-95f3ff56eb574dcc9b2090a50ad45296
Source dataset
uspto-grants-2012_07
Patent number
US08217060B2

Reaction notes

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