Methyl acetoacetate → methyl 4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carboxylate

HRID 1058680Notes

Reaction equation

HRID 1058680 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.[C:11]([O:17][CH3:18])(=[O:16])[CH2:12][C:13]([CH3:15])=O.[NH2:19][C:20]1[CH2:24][CH2:23][C:22](=[O:25])[CH:21]=1>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:12]([C:11]([O:17][CH3:18])=[O:16])=[C:13]([CH3:15])[NH:19][C:20]3[CH2:24][CH2:23][C:22](=[O:25])[C:21]2=3)[CH:7]=[CH:8][C:9]=1[F:10]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 122914403-Aminocyclopent-2-en-1-one

Product 1

HCID 11383413methyl 4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carboxylateYield 40.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Bromo-4-fluorobenzaldehyde (3.045 g, 15 mmol), methyl acetoacetate (2.09 g, 18 mmol) and 3-aminocyclopent-2-enone (1.45 g, 15 mmol) were heated to 65° C. in methyl alcohol for 5 days. The reaction was allowed to cool to ambient temperature and the white precipitate collected, washed with methyl alcohol and dried to provide 2.29 g of the title compound. Flash chromatography (5% methyl alcohol/methylene chloride) of the filtrate provided an additional 1.46 g of the title compound.

Workup

  1. customthe white precipitate collected
  2. washwashed with methyl alcohol
  3. customdried

Sources & evidence

ORD record
ord-f8e08f378d6045ff938a4d0e284108f6
Source dataset
uspto-grants-2003_02
Patent number
US06518279B2

Reaction notes

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