Dibenzyl-[3-(1-ethyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-amine → 3-(1-Ethyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-2,4-difluoro-phenylamine

HRID 45847Notes

Reaction equation

HRID 45847 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][N:18]([CH2:27][CH3:28])[N:17]=2)[C:10]=1[F:29])C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH2:27]([N:18]1[CH:19]=[C:20]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[C:16]([C:11]2[C:10]([F:29])=[C:9]([NH2:8])[CH:14]=[CH:13][C:12]=2[F:15])=[N:17]1)[CH3:28]

Participants

4

Reactant 1

HCID 67185128Dibenzyl-[3-(1-ethyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-amine

Product 1

HCID 671844933-(1-Ethyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-2,4-difluoro-phenylamineYield 79%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Dibenzyl-[3-(1-ethyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-amine (2.35 g, 4.89 mmol) was dissolved in methanol (140 mL). 20% Palladium hydroxide on carbon (500 mg) was added and the reaction was stirred under hydrogen atmosphere (50 psi) for 7 h. A further addition of catalyst was made (500 mg) and hydrogenation was continued for 6 more hours. The reaction mixture was filtered over a Celite pad and then concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel (DCM/methanol 95:5) to give 1.16 g of the desired product as a colourless foam (79% yield).

Workup

  1. additionA further addition of catalyst
  2. filtrationThe reaction mixture was filtered over a Celite pad
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by flash chromatography on silica gel (DCM/methanol 95:5)

Sources & evidence

ORD record
ord-de3be7b8898f4c8c819a129b28cc2af1
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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