Ammonium Chloride → Ethyl 5-bromo-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

HRID 751620Notes

Reaction equation

HRID 751620 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5](=O)[CH2:6][C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][N:10]=[C:9]([Br:16])[CH:8]=1)[CH3:2].[Cl-].[NH4+]>C1COCC1.C(O)C.[Fe]>[CH2:1]([O:3][C:4]([C:5]1[NH:13][C:12]2=[CH:11][N:10]=[C:9]([Br:16])[CH:8]=[C:7]2[CH:6]=1)=[O:18])[CH3:2]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 597536233-(2-Bromo-5-nitropyridin-4-yl)-2-oxopropionic acid ethyl ester

Product 1

HCID 50998338Ethyl 5-bromo-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Route A: To a solution of 3-(2-bromo-5-nitropyridin-4-yl)-2-oxopropionic acid ethyl ester (Preparation 25, 3.38 g, 10.7 mmol) in THF (50 mL) and ethanol (100 mL) was added saturated ammonium chloride solution (50 mL) and iron powder (3.57 g, 64.0 mmol) and the reaction heated under reflux for 2 h. The reaction mixture was filtered through celite and washed several times with ethyl acetate. The solvent was removed in vacuo and the remainder partitioned between saturated sodium hydrogen carbonate solution (100 mL) and ethyl acetate (3×150 mL). The combined organic fractions were dried (MgSO4) and concentrated in vacuo to give the title compound as a brown solid. δH (CD3OD): 1.42 (3H, t), 4.43 (2H, q), 7.14 (1H, s), 7.85 (1H, s), 8.58 (1H, s); m/z (ES+)=269 [M+H]+.

Workup

  1. temperaturethe reaction heated
  2. temperatureunder reflux for 2 h
  3. filtrationThe reaction mixture was filtered through celite
  4. washwashed several times with ethyl acetate
  5. customThe solvent was removed in vacuo
  6. customthe remainder partitioned between saturated sodium hydrogen carbonate solution (100 mL) and ethyl acetate (3×150 mL)
  7. dry with materialThe combined organic fractions were dried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f8e0e3ed12f494d87ffa163da5206e0
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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