3-Bromo-4-fluorobenzaldehyde → Methyl 7-benzyl-4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydro[1,7]naphthyridine-3-carboxylate

HRID 478281Notes

Reaction equation

HRID 478281 reaction equation
[NH2:1]/[C:2](/[CH3:8])=[CH:3]\[C:4]([O:6][CH3:7])=[O:5].[Br:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])[CH:13]=O.[CH2:19]([N:26]1[CH2:31][C:30](=O)[CH2:29][C:28](=[O:33])[CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[CH2:19]([N:26]1[CH2:31][C:30]2[NH:1][C:2]([CH3:8])=[C:3]([C:4]([O:6][CH3:7])=[O:5])[CH:13]([C:12]3[CH:15]=[CH:16][C:17]([F:18])=[C:10]([Br:9])[CH:11]=3)[C:29]=2[C:28](=[O:33])[CH2:27]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 1736043-Bromo-4-fluorobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 111381741-Benzylpiperidine-3,5-dione

Product 1

HCID 11397579Methyl 7-benzyl-4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydro[1,7]naphthyridine-3-carboxylateYield 53.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 3-aminocrotonate (0.58 g, 5 mmol), 3-bromo-4-fluorobenzaldehyde (1.0 g, 5 mmol) and N-benzylpiperidine-3,5-dione (Ziegler, J. Amer. Chem. Soc. (1973), 95, 7458-7464) (1.1 g, 5 mmol) in ethanol (5 mL) was heated at reflux in a sealed tube for 24 hours and concentrated. Purification of the residue on silica gel eluting with 5% ethanol/methylene chloride provided the title compound (1.3 g) as a yellow foam.

Workup

  1. temperatureat reflux in a sealed tube for 24 hours
  2. concentrationconcentrated
  3. customPurification of the residue on silica gel eluting with 5% ethanol/methylene chloride

Sources & evidence

ORD record
ord-c188213bef0140bb940aca3d4b7ef567
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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