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

HRID 875383Notes

Reaction equation

HRID 875383 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-51e9f70625834fada9fe65e36c7b0bfb
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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