HCID 66858341, compound → HCID 50989669, compound

HRID 1803138Notes

Reaction equation

HRID 1803138 reaction equation
Cl[C:2]1[N:3]=[CH:4][N:5]([C:7]2[C:12]([F:13])=[CH:11][C:10]([N+:14]([O-])=O)=[CH:9][C:8]=2[F:17])[CH:6]=1.ClC1N=CN(C2C(F)=CC(N)=CC=2F)C=1>[Pd].CCO>[F:13][C:12]1[CH:11]=[C:10]([CH:9]=[C:8]([F:17])[C:7]=1[N:5]1[CH:6]=[CH:2][N:3]=[CH:4]1)[NH2:14]

Participants

5

Reactant 2

HCID 66858341HCID 66858341, compoundHCID 66858397HCID 66858397, compound

Product 1

HCID 50989669HCID 50989669, compoundYield 116.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Step J (2): 10% Palladium on carbon (0.500 g) was added under an atmosphere of nitrogen to a solution of 4-chloro-1-(2,6-difluoro-4-nitrophenyl)-1H-imidazole (1.9 g, 7.32 mmol) in EtOH (30 mL). The flask was repeated evacuated and flushed with hydrogen gas (double balloon). The resulting mixture was allowed to warm to rt and left to stir for 1.5 h under the hydrogen atmosphere. Purged with nitrogen gas. Filtered the crude reaction mixture through a short plug of diatomaceous earth (Celite®). Rinsed reaction vessel and plug with methanol. Concentrated filtrate in vacuo. Dried residue on high vacuum overnight to afford a 1:1 mixture of 4-(4-chloro-1H-imidazol-1-yl)-3,5-difluoroaniline and 3,5-difluoro-4-(1H-imidazol-1-yl)aniline (1.67 g, ˜99% yield). LC-MS (M+H)+ 230.1 and 196.2.

Workup

  1. customThe flask was repeated evacuated
  2. customflushed with hydrogen gas (double balloon)
  3. waitleft
  4. customPurged with nitrogen gas
  5. filtrationFiltered the crude
  6. customreaction mixture through a short plug of diatomaceous earth (Celite®)
  7. washRinsed
  8. customreaction vessel and plug with methanol
  9. customDried residue on high vacuum overnight to afford

Sources & evidence

ORD record
ord-63ac10061d654614ae21ff01065b6a05
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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