Methyl 2-benzyl-9-bromo-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate → Methyl 2-benzyl-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate

HRID 521427

Reaction equation

HRID 521427 reaction equation
[CH2:1]([N:8]1[CH2:17][C:16]2[NH:15][C:14]3[C:18](Br)=[CH:19][CH:20]=[C:21]([C:22]([O:24][CH3:25])=[O:23])[C:13]=3[C:12](=[O:27])[C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO.[Pd]>[CH2:1]([N:8]1[CH2:17][C:16]2[NH:15][C:14]3[CH:18]=[CH:19][CH:20]=[C:21]([C:22]([O:24][CH3:25])=[O:23])[C:13]=3[C:12](=[O:27])[C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 89657401Methyl 2-benzyl-9-bromo-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 121297550Methyl 2-benzyl-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylateYield 62.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 2-benzyl-9-bromo-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate (0.1 g, 0.23 mmol) in MeOH (3 mL) was added Pd/C (0.04 g, 5%, 50% water), and the mixture was stirred at atmosphere of hydrogen for about 2.5 h. Debromination occurred without substantially removing benzyl group under this condition. Then the mixture was filtered, washed with MeOH (50 mL), concentrated and was chromatographed on silica gel to afford the product (0.05 g). MS (ESI) m/e [M+1]+ 349.0.

Workup

  1. filtrationThen the mixture was filtered
  2. washwashed with MeOH (50 mL)
  3. concentrationconcentrated
  4. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-7c0fa855a02548d2bb2bdab4f0453e03
Source dataset
uspto-grants-2016_05
Patent number
US09328111B2

Linked notes

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