Methyl 7-benzyl-4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydro[1,7]naphthyridine-3-carboxylate → 6-benzyl-9-(3-bromo-4-fluorophenyl)-5,6,7,9-tetrahydrofuro[3,4-b][1,7]naphthyridine-1,8(3H,4H)-dione

HRID 478282Notes

Reaction equation

HRID 478282 reaction equation
[CH2:1]([N:8]1[CH2:17][C:16]2[NH:15][C:14](C)=[C:13]([C:19]([O:21][CH3:22])=[O:20])[CH:12]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[C:25]([Br:30])[CH:24]=3)[C:11]=2[C:10](=[O:31])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:17][C:16]2[NH:15][C:14]3[CH2:22][O:21][C:19](=[O:20])[C:13]=3[CH:12]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[C:25]([Br:30])[CH:24]=3)[C:11]=2[C:10](=[O:31])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11397579Methyl 7-benzyl-4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydro[1,7]naphthyridine-3-carboxylateHCID 21124087Pyridiniumtribromide

Product 1

HCID 111788566-benzyl-9-(3-bromo-4-fluorophenyl)-5,6,7,9-tetrahydrofuro[3,4-b][1,7]naphthyridine-1,8(3H,4H)-dioneYield 71%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of the product from Example 39A (3.1 g, 6.3 mmol) in chloroform (50 mL) was cooled to 0° C., treated with 90% pyridinium tribromide (2.45 g, 6.9 mmol), warmed to abmient temperature, stirred for 16 hours and washed with water. The chloroform layer was isolated, dried (MgSO4), filtered, refluxed for 16 hours and cooled in an ice bath. The resulting precipitate was collected by filtration and dried to provide the title compound (2.1 g) as tan crystals.

Workup

  1. temperaturewarmed
  2. washwashed with water
  3. customThe chloroform layer was isolated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. temperaturerefluxed for 16 hours
  7. temperaturecooled in an ice bath
  8. filtrationThe resulting precipitate was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-2bafe32d67364d80ae2fc5a78759fadd
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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