N-bromobutanimide → 9-(3,4-dibromophenyl)-5,9-dihydro-3H-furo [3,4-b]pyrano[4,3-e]pyridine-1,8(4H,7H)-dione

HRID 478301Notes

Reaction equation

HRID 478301 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]([CH3:19])[NH:12][C:11]3[CH2:20][O:21][CH2:22][C:23](=[O:24])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[Br:8].BrN1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:10]3[C:23](=[O:24])[CH2:22][O:21][CH2:20][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[Br:8]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 18001000methyl 4-(3,4-dibromophenyl)-2-methyl-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylate

Product 1

HCID 102750469-(3,4-dibromophenyl)-5,9-dihydro-3H-furo [3,4-b]pyrano[4,3-e]pyridine-1,8(4H,7H)-dioneYield 46.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
110 °C

Procedure

The product from Example 71A (0.095 g, 0.21 mmol) in chloroform (5 mL) was treated with N-bromosuccinimide (0.037 g, 0.21 mmol) and heated to 110° C. for 16 hours. The mixture was cooled to ambient temperature and purified by chromatography on silica gel eluting with 5% methanol in dichloromethane to provide the title compound (0.043 g).

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. custompurified by chromatography on silica gel eluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-f2ff994bb75e4afd8eafa98b5dfaed36
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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