Ethanol → 3-(1-Methyl-piperidin-4-yl)-1H-pyrrolo[3,2-b]pyridin-5-ylamine

HRID 581233Notes

Reaction equation

HRID 581233 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[C:8]([C:11]3[CH2:12][CH2:13][N:14]([CH3:17])[CH2:15][CH:16]=3)=[CH:9][NH:10][C:5]2=[CH:4][CH:3]=1.C(O)C>[Pd].CO>[NH2:1][C:2]1[N:7]=[C:6]2[C:8]([CH:11]3[CH2:12][CH2:13][N:14]([CH3:17])[CH2:15][CH2:16]3)=[CH:9][NH:10][C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 10988008HCID 10988008, compound

Product 1

HCID 102202303-(1-Methyl-piperidin-4-yl)-1H-pyrrolo[3,2-b]pyridin-5-ylamineYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 21 gm (89.9 mMol) 5-amino-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrrolo[3,2-b]pyridine and 10% palladium on carbon pre-wet with 30 mL ethanol in 180 mL methanol were hydrogenated at 65 p.s.i for 3 days. The catalyst was removed by filtration and the filtrate concentrated under reduced pressure. The residual solid was slurried in 120 mL ethyl acetate, filtered, and washed 3×30 mL ethyl acetate. The remaining solid was dried under reduced pressure to provide 19 gm (92%) the title compound as a light brown solid.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate concentrated under reduced pressure
  3. filtrationfiltered
  4. washwashed 3×30 mL ethyl acetate
  5. customThe remaining solid was dried under reduced pressure

Sources & evidence

ORD record
ord-ecaca1bea92f4b92becd7f44793508ec
Source dataset
uspto-grants-1999_07
Patent number
US05919936

Reaction notes

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