methyl 4-(3-bromo-4-fluorophenyl)-2-(bromomethyl)-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylate → 9-(3-bromo-4-fluorophenyl)-5,9-dihydro-3H-furo [3,4-b]pyrano[4,3-e]pyridine-1,8(4H,7H)-dione

HRID 478272Notes

Reaction equation

HRID 478272 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:14]([C:15]([O:17]C)=[O:16])=[C:13]([CH2:19]Br)[NH:12][C:11]3[CH2:21][O:22][CH2:23][C:24](=[O:25])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[F:8]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:10]3[C:24](=[O:25])[CH2:23][O:22][CH2:21][C:11]=3[NH:12][C:13]3[CH2:19][O:16][C:15](=[O:17])[C:14]2=3)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

3

Reactant 1

HCID 11328992methyl 4-(3-bromo-4-fluorophenyl)-2-(bromomethyl)-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylate

Product 1

HCID 99297439-(3-bromo-4-fluorophenyl)-5,9-dihydro-3H-furo [3,4-b]pyrano[4,3-e]pyridine-1,8(4H,7H)-dioneYield 30.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 25B (0.30 g, 0.63 mmol) was heated neat under a nitrogen atmosphere to 130° C. for 15 minutes and cooled to ambient temperature. The residue was treated with methylene chloride and the resulting solid was collected by filtration, washed with methylene chloride and dried to provide the title compound (0.074 g) as a white solid.

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with methylene chloride
  3. customdried

Sources & evidence

ORD record
ord-f4dbe826e82a43a2bfddab829895fae9
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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