4-[(6-Chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluoroaniline → 4-((1H-Pyrrolo[2,3-B]pyridin-4-YL)oxy)-3-fluoroaniline

HRID 16406Notes

Reaction equation

HRID 16406 reaction equation
Cl[C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[C:4]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:13]=2[F:19])[CH:3]=1>C(O)C.[Pd]>[F:19][C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][C:12]=1[O:11][C:4]1[CH:3]=[CH:2][N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]=12)[NH2:18]

Participants

4

Reactant 1

HCID 179792844-[(6-Chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluoroaniline

Product 1

HCID 160379654-((1H-Pyrrolo[2,3-B]pyridin-4-YL)oxy)-3-fluoroaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3.2 g (11.5 mmol) of {4-[(6-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluoro-phenyl}amine (from example XXXI) are dissolved in ethanol at 50° C. The solution is then allowed to cool to RT, and 2.45 g (2.30 mmol) of 10% palladium on activated carbon are added. The mixture is hydrogenated overnight under a hydrogen pressure of 2 bar. The palladium is then filtered off with suction through kieselguhr and washed with ethanol, and the filtrate is concentrated.

Workup

  1. filtrationThe palladium is then filtered off with suction through kieselguhr
  2. washwashed with ethanol
  3. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-8250920d3c004238aa766417baf09bde
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Reaction notes

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