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 635983Notes

Reaction equation

HRID 635983 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 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-9cd9257503764d9194a89addfb3875f2
Source dataset
uspto-grants-2001_02
Patent number
US06191140B1

Reaction notes

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