HCID 178505869, compound → HCID 178507659, compound

HRID 1843632Notes

Reaction equation

HRID 1843632 reaction equation
C([N:8](CC1C=CC=CC=1)[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([C:16]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[CH:19][NH:18][N:17]=2)[C:10]=1[F:27])C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[F:27][C:10]1[C:11]([C:16]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[CH:19][NH:18][N:17]=2)=[C:12]([F:15])[CH:13]=[CH:14][C:9]=1[NH2:8]

Participants

4

Reactant 1

HCID 178505869HCID 178505869, compound

Product 1

HCID 178507659HCID 178507659, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To dibenzyl-[2,4-difluoro-3-(4-pyridin-4-yl-1H-pyrazol-3-yl)-phenyl]-amine (1.795 g, 3.97 mmol) in methanol (100 mL) was added 20% palladium hydroxide on carbon (646 mg). The reaction was stirred under hydrogen atmosphere for 12 hours (45 psi). The reaction was filtered to remove the catalyst, and then concentrated under reduced pressure. The crude was purified by silica gel column chromatography eluting with methanol 7% in methylene chloride to give 2,4-difluoro-3-(4-pyridin-4-yl-1H-pyrazol-3-yl)-phenylamine (yield 56% over three steps).

Workup

  1. filtrationThe reaction was filtered
  2. customto remove the catalyst
  3. concentrationconcentrated under reduced pressure
  4. customThe crude was purified by silica gel column chromatography
  5. washeluting with methanol 7% in methylene chloride

Sources & evidence

ORD record
ord-1e6623a1f83442b1a7afa3436688225c
Source dataset
uspto-grants-2015_02
Patent number
US08946250B2

Reaction notes

Loading…