Acetic Anhydride → N-(1-acetyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-acetamide

HRID 2247234Notes

Reaction equation

HRID 2247234 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.[C:22](OC(=O)C)(=[O:24])[CH3:23]>[Pd].CCOC(C)=O>[C:1]([N:4]1[C:8]2=[N:9][CH:10]=[CH:11][C:12]([CH2:13][NH:14][C:22](=[O:24])[CH3:23])=[C:7]2[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 219614211-Acetyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile

Product 1

HCID 21961391N-(1-acetyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-acetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-acetyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile (0.691 g, example 15), 10% Pd/C (0.702 g), 5 mL of Et3N, and 20 mL of EtOAc was added acetic anhydride (1.0 mL). The mixture 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 white residue, which was purified by chromatography through silica gel (150 g, 1 to 5% MeOH/CHCl3 with 1% NH4OH, stepwise gradient) to afford N-(1-acetyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-acetamide 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 white residue, which
  4. customwas purified by chromatography through silica gel (150 g, 1 to 5% MeOH/CHCl3 with 1% NH4OH, stepwise gradient)

Sources & evidence

ORD record
ord-09ce10fc33d44c6c93b6866492e3b1ec
Source dataset
uspto-grants-2010_03
Patent number
US07687643B2

Reaction notes

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