2H-pyran-3,5(4H,6H)-dione → methyl 4-(3,4-dibromophenyl)-2-methyl-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylate

HRID 478300

Reaction equation

HRID 478300 reaction equation
[O:1]1[CH2:6][C:5](=O)[CH2:4][C:3](=[O:8])[CH2:2]1.[Br:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[Br:18])[CH:13]=O.[NH2:19]/[C:20](/[CH3:26])=[CH:21]\[C:22]([O:24][CH3:25])=[O:23]>C(O)C>[Br:9][C:10]1[CH:11]=[C:12]([CH:13]2[C:21]([C:22]([O:24][CH3:25])=[O:23])=[C:20]([CH3:26])[NH:19][C:5]3[CH2:6][O:1][CH2:2][C:3](=[O:8])[C:4]2=3)[CH:15]=[CH:16][C:17]=1[Br:18]

Participants

5

Reactant 3

HCID 3252872H-pyran-3,5(4H,6H)-dioneHCID 6220533,4-DibromobenzaldehydeHCID 643918Methyl 3-aminocrotonate

Product 1

HCID 18001000methyl 4-(3,4-dibromophenyl)-2-methyl-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylateYield 65.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 11B (0.17 g, 1.5 mmol), the product from 3,4-dibromobenzaldehyde (0.53 g, 2.0 mmol) and methyl 3-aminocrotonate (0.15 g, 1.3 mmol) in ethanol (8 mL) were heated at 80° C. in a sealed tube for 60 hours and then cooled to ambient temperature. The mixture was filtered and the filter cake was washed with ethanol and dried to provide the title compound (0.39 g).

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake was washed with ethanol
  3. customdried

Sources & evidence

ORD record
ord-08abae15238d4a958673daa9e80be9a5
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Linked notes

Loading…