Triethylamine → 1-(4-(Aminomethyl)-1H-pyrrolo[2,3-b]pyridin-1-yl)ethanone

HRID 887647Notes

Reaction equation

HRID 887647 reaction equation
[C:1]([N:4]1[C:8]2[N:9]=[CH:10][CH:11]=[C:12]([C:13]#[N:14])[C:7]=2[CH:6]=[CH:5]1)(=[O:3])[CH3:2].CCN(CC)CC>[Pd].CCO>[NH2:14][CH2:13][C:12]1[CH:11]=[CH:10][N:9]=[C:8]2[N:4]([C:1](=[O:3])[CH3:2])[CH:5]=[CH:6][C:7]=12

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 219614211-Acetyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile

Product 1

HCID 219614331-(4-(Aminomethyl)-1H-pyrrolo[2,3-b]pyridin-1-yl)ethanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-acetyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile (0.872 g, step D), 10% Pd/C (0.882 g), 20 mL of Et3N, and 80 mL of EtOH was stirred at RT under balloon pressure of H2 for overnight. Solid was removed by filtration through a pad of Celite® and the filtrate was concentrated to yield a cream color residue, which was purified by chromatography through silica gel (70 g, 2 to 5% MeOH/CHCl3 with 1% NH4OH) to afford 1-(4-aminomethyl-pyrrolo[2,3-b]pyridin-1-yl)-ethanone as a white solid.

Workup

  1. customSolid was removed by filtration through a pad of Celite®
  2. concentrationthe filtrate was concentrated
  3. customto yield a cream color residue, which
  4. customwas purified by chromatography through silica gel (70 g, 2 to 5% MeOH/CHCl3 with 1% NH4OH)

Sources & evidence

ORD record
ord-4737f12146bb4582b8d3c3d1a7b8a3e8
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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