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)-2,3,5,9-tetrahydropyrano[3,4-b]pyrrolo[3,4-e]pyridine-1,8(4H,7H)-dione

HRID 635985Notes

Reaction equation

HRID 635985 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:14]([C:15]([O:17]C)=O)=[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].[NH3:26].CO>>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:14]3[C:15](=[O:17])[NH:26][CH2:19][C:13]=3[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]

Participants

3

Reactant 2

HCID 11328992methyl 4-(3-bromo-4-fluorophenyl)-2-(bromomethyl)-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylateHCID 21705897Ammonia methanol

Product 1

HCID 99296869-(3-bromo-4-fluorophenyl)-2,3,5,9-tetrahydropyrano[3,4-b]pyrrolo[3,4-e]pyridine-1,8(4H,7H)-dione

Procedure

The product from Example 25B (0.22 g, 0.46 mmol) was treated with 1:1 ammonia/methanol mixture (60 mL) in a metal Parr stirred reactor for 2.5 days at ambient temperature. The solvent was allowed to evaporate and the residue was purified by chromatography on silica gel (5% and then 10% methanol in methylene chloride) to provide the title compound (0.026 g) as a solid.

Workup

  1. customto evaporate
  2. customthe residue was purified by chromatography on silica gel (5%

Sources & evidence

ORD record
ord-0ec47ad660c64b2a840227ca2d063614
Source dataset
uspto-grants-2001_02
Patent number
US06191140B1

Reaction notes

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