2-(4-Nitrophenyl)-4-(4-fluorophenyl)-5-(4-pyridinyl)-1H-imidazole → 4-[4-(4-Fluorophenyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]benzenamine

HRID 1417080Notes

Reaction equation

HRID 1417080 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=3)[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1>[Pd]>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([C:10]2[NH:11][C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[N:9]=2)=[CH:20][CH:21]=1

Participants

3

Reactant 1

HCID 47122-(4-Nitrophenyl)-4-(4-fluorophenyl)-5-(4-pyridinyl)-1H-imidazole

Product 1

HCID 99020414-[4-(4-Fluorophenyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]benzenamine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture containing 4-(4-fluorophenyl)-2-(4-nitrophenyl)-5-(4-pyridyl)-1H-imidazole (2.0 g, 5.6 mmol) [See Ex. 26 above] and 10% palladium on activated carbon (0.4 g) was stirred under an atmosphere of H2 for 4 h, then was filtered through a pad of Celite. The filtrate was concentrated under reduced pressure, and the residue was purified by flash chromatography, eluting with a solvent gradient of 1-10% MeOH/CHCl3. The title compound was obtained as a light orange solid (0.50 g, 27%): 1H NMR (DMSO-d6): d 8.40 (d, 2H); 7.73 (d, 2H); 7.57 (m, 2H); 7.35 (m, 4H); 6.62 (t, 2H).

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 a solvent gradient of 1-10% MeOH/CHCl3

Sources & evidence

ORD record
ord-5a8c855155b84149ae3408366be209bd
Source dataset
uspto-grants-1999_06
Patent number
US05916891

Reaction notes

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