Ethanol → 1-Benzyl-5-hydroxy-2-oxo-1,2,3,4-tetrahydro-[1,7]naphthyridine-6-carboxylic acid methyl ester

HRID 919657Notes

Reaction equation

HRID 919657 reaction equation
CCO.[CH3:4][O:5][C:6]([C:8]1[C:9]([OH:27])=[C:10]2[C:15](=[CH:16][N:17]=1)[N:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13](=[O:25])[C:12](Br)=[CH:11]2)=[O:7].C([O-])(=O)C.[Na+]>[Pd].CCOC(C)=O>[CH3:4][O:5][C:6]([C:8]1[C:9]([OH:27])=[C:10]2[C:15](=[CH:16][N:17]=1)[N:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13](=[O:25])[CH2:12][CH2:11]2)=[O:7]

Participants

6

Reactant 3

HCID 702EthanolHCID 517045Sodium AcetateHCID 682974771-Benzyl-3-bromo-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester

Product 1

HCID 682972871-Benzyl-5-hydroxy-2-oxo-1,2,3,4-tetrahydro-[1,7]naphthyridine-6-carboxylic acid methyl esterYield 62.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A flask was charged with EtOH (10 mL) and 10% palladium on carbon (200 mg). A solution of 1-benzyl-3-bromo-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (150 mg, 0.39 mmol) in EtOAc (40 mL) and sodium acetate (47 mg, 0.58 mmol) were added, and the resulting mixture was stirred under H2 atmosphere for 16 h. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was chromatographed (0-60% EtOAc/hexanes+2% AcOH) to give 76 mg of the title compound as a white solid. MS: (+) m/z 325.11 (M+1).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was chromatographed (0-60% EtOAc/hexanes+2% AcOH)

Sources & evidence

ORD record
ord-828519405c6d4aca969ee6f84631aa1d
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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