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 2192155Notes

Reaction equation

HRID 2192155 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:18]=[CH:17][C:15]([NH2:16])=[CH:14][C:13]=2[F:19])[CH:3]=1>C(O)C.[Pd]>[F:19][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][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)[NH2:16]

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-fluoroaniline 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-carbon are added. The mixture is hydrogenated under a hydrogen pressure of 2 bar overnight. The mixture is, then filtered off with suction through kieselguhr, the kieselguhr is washed with ethanol and the filtrate is concentrated.

Workup

  1. custompressure of 2 bar overnight
  2. filtrationfiltered off with suction through kieselguhr
  3. washthe kieselguhr is washed with ethanol
  4. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-5406af31f2664469b32940118651149e
Source dataset
uspto-grants-2012_12
Patent number
US08329716B2

Reaction notes

Loading…