2H-pyran-3,5(4H,6H)-dione → 4-(3-bromo-4-methylphenyl)-1-methyl-4,9-dihydro-1H-isoxazolo [3,4-b]pyrano[4,3-e]pyridine-3,5(6H,8H)-dione

HRID 1837103Notes

Reaction equation

HRID 1837103 reaction equation
[NH2:1][C:2]1[N:3]([CH3:8])[O:4][C:5](=[O:7])[CH:6]=1.[CH3:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][C:11]=1[Br:18].[O:19]1[CH2:24][C:23](=O)[CH2:22][C:21](=[O:26])[CH2:20]1>C(O)C>[Br:18][C:11]1[CH:12]=[C:13]([CH:14]2[C:22]3[C:21](=[O:26])[CH2:20][O:19][CH2:24][C:23]=3[NH:1][C:2]3[N:3]([CH3:8])[O:4][C:5](=[O:7])[C:6]2=3)[CH:16]=[CH:17][C:10]=1[CH3:9]

Participants

5

Reactant 3

HCID 3252872H-pyran-3,5(4H,6H)-dioneHCID 8167653-Bromo-4-methylbenzaldehydeHCID 234974983-Amino-2-methyl-2,5-dihydro-1,2-oxazol-5-one

Product 1

HCID 102938104-(3-bromo-4-methylphenyl)-1-methyl-4,9-dihydro-1H-isoxazolo [3,4-b]pyrano[4,3-e]pyridine-3,5(6H,8H)-dioneYield 17.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

The product from Example 45A (0.11 g, 1 mmol), 4-methyl-3-bromobenzaldehyde (0.2 g, 1 mmol), prepared as described in (Pearson et al., J.Org. Chem.(1958),23,1412-1416) and 2H-pyran-3,5(4H,6H)-dione (0.11 g, 1 mmol) in ethyl alcohol (2 mL) were heated at 80° C. for 2 days in a sealed tube. The reaction mixture was allowed to cool to ambient temperature and was evaporated under reduced pressure. The residue was chromatographed eluting with 19:0.5:0.5 ethylacetate:formic acid:water to provide the title compound (0.07 g).

Workup

  1. temperatureto cool to ambient temperature
  2. customwas evaporated under reduced pressure
  3. customThe residue was chromatographed
  4. washeluting with 19:0.5:0.5 ethylacetate

Sources & evidence

ORD record
ord-acfb2507e2fe4ba487c1959f81296bba
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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