Acetic Acid → N-(1H-Pyrrolo[2,3-c]pyridin-5-yl)acetamide

HRID 2201776Notes

Reaction equation

HRID 2201776 reaction equation
CN(C)/[CH:3]=[CH:4]\[C:5]1[C:10]([N+:11]([O-])=O)=[CH:9][N:8]=[C:7]([NH:14][C:15](=[O:17])[CH3:16])[CH:6]=1.C(O)(=O)C>CO.ClCCl.[Pd]>[NH:11]1[C:10]2=[CH:9][N:8]=[C:7]([NH:14][C:15](=[O:17])[CH3:16])[CH:6]=[C:5]2[CH:4]=[CH:3]1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 86720622N-{4-[(Z)-2-(dimethylamino)ethenyl]-5-nitropyridin-2-yl}acetamide

Product 1

HCID 18975304N-(1H-Pyrrolo[2,3-c]pyridin-5-yl)acetamideYield 71%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-{4-[(Z)-2-(dimethylamino)ethenyl]-5-nitropyridin-2-yl}acetamide (0.7 g, 3 mmol, Step b) in methanol and dichloromethane (5:1, 120 mL), palladium on carbon (0.4 g) was added followed by addition of acetic acid (7 mL). The reaction mixture was then purged with hydrogen gas and stirred overnight at room temperature. The resulting mixture was filtered over celite bed, and the residue was washed with methanol (100 mL). The combined filtrate was concentrated under vacuum and purified by silica gel column chromatography using methanol in dichloromethane (2%) to afford N-(1H-pyrrolo[2,3-c]pyridin-5-yl)acetamide (0.35 g, 71%).

Workup

  1. customThe reaction mixture was then purged with hydrogen gas
  2. filtrationThe resulting mixture was filtered over celite bed
  3. washthe residue was washed with methanol (100 mL)
  4. concentrationThe combined filtrate was concentrated under vacuum
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-26f574d25e514996baed44c8fd8b2da6
Source dataset
uspto-grants-2016_06
Patent number
US09364466B2

Reaction notes

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