Ethyl Acetate → 4-bromo-7-methoxy-1H-pyrrolo[2,3-c]pyridine

HRID 632738Notes

Reaction equation

HRID 632738 reaction equation
[Br:1][C:2]1[C:3](/[CH:13]=[CH:14]/[N:15](C)C)=[C:4]([N+]([O-])=O)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.C(OCC)(=O)C.[H][H]>[Ni].O>[Br:1][C:2]1[CH:7]=[N:6][C:5]([O:8][CH3:9])=[C:4]2[NH:15][CH:14]=[CH:13][C:3]=12

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 578831255-Bromo-4-[2-(dimethylamino)ethenyl]-2-methoxy-3-nitropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 118064014-bromo-7-methoxy-1H-pyrrolo[2,3-c]pyridineYield 56%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

(E)-2-(5-bromo-2-methoxy-3-nitropyridin-4-yl)-N,N-dimethylethenamine (13.9 g, 45.8 mmol) and ethyl acetate (150 mL) were added to Ra-Ni 2800 (pre-washed with ethanol), water slurry (6.9 g, 118 mmol) in a stainless steel pressure bottle and stirred for 30 minutes at 30 psi of hydrogen and room temperature. The reaction mixture was filtered, and concentrated. The residue was triturated with dichloromethane, and the solid collected by filtration to provide 4-bromo-7-methoxy-1H-pyrrolo[2,3-c]pyridine (5.82 g). The mother liquor was evaporated and the residue triturated again with dichloromethane and filtered to provide an additional 1.63 g of 4-bromo-7-methoxy-1H-pyrrolo[2,3-c]pyridine. Total yield=7.45 g, 72% yield.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was triturated with dichloromethane
  4. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-27ce196fe184401ba5f89d17b8a77a7d
Source dataset
uspto-grants-2016_04
Patent number
US09321765B2

Reaction notes

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