Ethyl 3-(3-nitropyridin-2-yl)-2-oxopropionate → ethyl 1H-pyrrolo(3,2-b)pyridine-2-carboxylate

HRID 1693369Notes

Reaction equation

HRID 1693369 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5](=O)[CH2:6][C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[CH:9][N:8]=1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C:5]1[NH:13][C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=[O:17])[CH3:2]

Participants

4

Reactant 1

HCID 59753617Ethyl 3-(3-nitropyridin-2-yl)-2-oxopropionate

Product 1

HCID 11579250ethyl 1H-pyrrolo(3,2-b)pyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 3-(3-nitropyridin-2-yl)-2-oxopropionic acid ethyl ester (Preparation 30, 1.00 g, 4.20 mmol) in ethanol (30 mL, absolute) was added palladium (10% on activated carbon, 447 mg, 0.42 mmol) and the reaction mixture placed under an atmosphere of hydrogen at a pressure of 20-30 psi for 12 h with vigorous stirring. The reaction mixture was filtered through celite, washing with ethyl acetate and the filtrate concentrated in vacuo to ca. 20 mL. Water (150 mL) was added and the mixture cooled to between 0° C. and 5° C. The precipitate that formed was collected by filtration and dried to give the title compound as a beige solid. δH (CDCl3): 1.44 (3H, t), 4.45 (2H, q), 7.25 (1H, dd), 7.39 (1H, s), 7.75 (1H, dd), 8.57 (1H, dd), 8.98 (1H, s).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashing with ethyl acetate
  3. concentrationthe filtrate concentrated in vacuo to ca. 20 mL
  4. additionWater (150 mL) was added
  5. temperaturethe mixture cooled to between 0° C. and 5° C
  6. customThe precipitate that formed
  7. filtrationwas collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-b0c2e989fadc42d7bcb88721c67d7dc9
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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