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

HRID 478273Notes

Reaction equation

HRID 478273 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].[CH3:26][NH2:27].CO>>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:14]3[C:15](=[O:17])[N:27]([CH3:26])[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

4

Reactant 3

HCID 887MethanolHCID 6329MethylamineHCID 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 98219069-(3-bromo-4-fluorophenyl)-2-methyl-2,3,5,9-tetrahydropyrano[3,4-b]pyrrolo[3,4-e]pyridine-1,8(4H,7H)-dione

Procedure

A solution of the product from Example 25B (0.16 g, 0.34 mmol) and 2M methyl amine in methanol (3.5 mL, 7.0 mmol) was stirred at ambient temperature for 16 hours and concentrated. Purification of the residue on silica gel (5% and then 10% methanol in methylene chloride) provided an oil which was crystallized from ethanol, collected by filtration and dried to yield the title compound (0.016 g) as a white solid.

Workup

  1. concentrationconcentrated
  2. customPurification of the residue on silica gel (5%
  3. custom10% methanol in methylene chloride) provided an oil which
  4. customwas crystallized from ethanol
  5. filtrationcollected by filtration
  6. customdried

Sources & evidence

ORD record
ord-75003a47bd2e42c0966de434ca4050fb
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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