HCID 19593091, compound → HCID 9884001, compound

HRID 613365Notes

Reaction equation

HRID 613365 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18]CC4C=CC=CC=4)=[CH:14][CH:13]=3)[N:9]=[C:8]2[C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[CH:3][CH:2]=1>[Pd].CCOC(C)=O>[N:1]1[CH:2]=[CH:3][C:4]([N:7]2[CH:11]=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=3)[N:9]=[C:8]2[C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 19593091HCID 19593091, compound

Product 1

HCID 9884001HCID 9884001, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture containing 1-(4-pyridyl)-2-(4-fluorophenyl)-4-(4-benzyloxyphenyl)imidazole (0.13 g, 0.3 mmol) and 10% palladium on activated carbon (100 mg) in EtOAc was stirred under an atmosphere of H2 for 10 h, at which time the reaction mixture was filtered through a pad of Celite. The filtrate was concentrated under reduced pressure, and the residue was purified by flash chromatography, eluting with 1:1 EtOAc/hexanes. The material which was isolated was crystallized from EtOAc/hexanes to afford the title compound (0.07 g, 70%). m.p. 230-231° C.

Workup

  1. filtrationwas filtered through a pad of Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by flash chromatography
  4. washeluting with 1:1 EtOAc/hexanes
  5. customThe material which was isolated
  6. customwas crystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-fcfcdd4845b14c9c8b9ac01f11473250
Source dataset
uspto-grants-1999_12
Patent number
US06008235

Reaction notes

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