Acetic Anhydride → HCID 69263705, compound

HRID 888123Notes

Reaction equation

HRID 888123 reaction equation
[NH:1]1[C:5]2[N:6]=[CH:7][CH:8]=[C:9]([C:10]#[N:11])[C:4]=2[CH:3]=[CH:2]1.[CH3:12][CH2:13][O:14]C(C)=O.[CH3:18][C:19](OC(C)=O)=[O:20]>[Pd].CCN(CC)CC>[C:13]([N:1]1[C:5]2=[N:6][CH:7]=[CH:8][C:9]([CH2:10][NH:11][C:19](=[O:20])[CH3:18])=[C:4]2[CH:3]=[CH:2]1)(=[O:14])[CH3:12]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 117151961H-pyrrolo(2,3-b)pyridine-4-carbonitrile

Product 1

HCID 69263705HCID 69263705, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

1H-Pyrrolo[2,3-b]pyridine-4-carbonitrile (11.2 g, 83.8 mmol) was dissolved into 400 mL EtOAc, 100 mL of Et3N. Pd/C (2.8 g) was added followed by 20 mL of Ac2O. H2 was introduced via balloon and the mixture was stirred at RT under balloon pressure of H2 for 8-12 h. After most of the starting material was consumed, catalyst was removed by filtration through a pad of Celite®. The pad was washed by EtOAc, CH2Cl2, and MeOH. The solvent was evaporated. The residue was taken into CH2Cl2 and the solid was collected by filtration to afford 471 g of N-((1-acetyl-1H-pyrrolo[2,3-b]pyridin-4-yl)methyl)acetamide. The filtrate was concentrated and purified on a column (0-10% MeOH/CH2Cl2+NH4OH) to obtain (N-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-acetamide.

Workup

  1. additionH2 was introduced via balloon
  2. customAfter most of the starting material was consumed
  3. customcatalyst was removed by filtration through a pad of Celite®
  4. washThe pad was washed by EtOAc, CH2Cl2, and MeOH
  5. customThe solvent was evaporated
  6. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-9a7669cf1c294b9983383ced9cb19684
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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