HCID 66859203, compound → HCID 58075671, compound

HRID 1803158Notes

Reaction equation

HRID 1803158 reaction equation
[F:1][CH:2]([F:19])[C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:9]=2[O:17][CH3:18])[CH:7]=1>[Pd].CO>[F:19][CH:2]([F:1])[C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=2[O:17][CH3:18])[CH:7]=1

Participants

4

Reactant 1

HCID 66859203HCID 66859203, compound

Product 1

HCID 58075671HCID 58075671, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Step N (4): 10% Palladium on carbon (250 mg) was added under an atmosphere of nitrogen to a solution of 4-(difluoromethyl)-1-(2-methoxy-4-nitrophenyl)-1H-imidazole (2.5 g, 92.9 mmol) in methanol (25 mL). The flask was repeatedly evacuated and flushed with hydrogen gas (double balloon). The resulting mixture was allowed to stir at rt for 2 h. The reaction vessel was purged with nitrogen gas. The crude reaction mixture was filtered through a short diatomaceous earth (Celite®) plug. Rinsed reaction vessel and plug with methanol. Concentrated filtrate in vacuo. The crude product was purified using silica gel column chromatography (EtOAc/hexane) to afford 4-(4-(difluoromethyl)-1H-imidazol-1-yl)-3-methoxyaniline (1.8 g, 81% yield). LC-MS (M+H)+ 240.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.42 (s, 1 H) 7.93 (s, 1 H) 7.47 (d, J=8.4 Hz, 1 H) 7.19-6.88 (m, 3 H) 3.81 (s, 3 H).

Workup

  1. customThe flask was repeatedly evacuated
  2. customflushed with hydrogen gas (double balloon)
  3. customThe reaction vessel was purged with nitrogen gas
  4. customThe crude reaction mixture
  5. filtrationwas filtered through a short diatomaceous earth (Celite®) plug
  6. washRinsed
  7. customreaction vessel and plug with methanol
  8. customThe crude product was purified

Sources & evidence

ORD record
ord-744cf7b94666407a8431c040b9cf029a
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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