3-Bromo-4-fluorobenzaldehyde → 2-benzyl-5-(3-bromo-4-fluorophenyl)-2,3,5,7,8,9-hexahydro-1H-cyclopenta[b][1,7]naphthyridine-4,6-dione

HRID 635971Notes

Reaction equation

HRID 635971 reaction equation
[NH2:1][C:2]1[CH2:6][CH2:5][C:4](=[O:7])[CH:3]=1.[Br:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[F:17])[CH:12]=O.[CH2:18]([N:25]1[CH2:30][C:29](=O)[CH2:28][C:27](=[O:32])[CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[CH2:18]([N:25]1[CH2:30][C:29]2[NH:1][C:2]3[CH2:6][CH2:5][C:4](=[O:7])[C:3]=3[CH:12]([C:11]3[CH:14]=[CH:15][C:16]([F:17])=[C:9]([Br:8])[CH:10]=3)[C:28]=2[C:27](=[O:32])[CH2:26]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 1736043-Bromo-4-fluorobenzaldehydeHCID 111381741-Benzylpiperidine-3,5-dioneHCID 122914403-Aminocyclopent-2-en-1-one

Product 1

HCID 113288132-benzyl-5-(3-bromo-4-fluorophenyl)-2,3,5,7,8,9-hexahydro-1H-cyclopenta[b][1,7]naphthyridine-4,6-dioneYield 64.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-amino-2-cyclopenten-1-one (Kikani, B. B., Synthesis, (1991), 2, 176) (0.97 g, 10 mmol), 3-bromo-4-fluorobenzaldehyde (2.0 g, 10 mmol) and N-benzylpiperidine-3,5-dione (Ziegler, J. Amer. Chem. Soc. (1973), 95, 7458-7464) (2.2 g, 10 mmol) in ethyl alcohol (10 mL) was heated to reflux for 72 hours and then allowed to cool to ambient temperature. The solvent was evaporated and the residue was purified by flash chromatography over silica gel (5% ethanol/methylene chloride) to provide the title compound (3.0 g).

Workup

  1. temperatureto reflux for 72 hours
  2. customThe solvent was evaporated
  3. customthe residue was purified by flash chromatography over silica gel (5% ethanol/methylene chloride)

Sources & evidence

ORD record
ord-58f8bb02fe4a456fbc8ac123f7d0819e
Source dataset
uspto-grants-2001_02
Patent number
US06191140B1

Reaction notes

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