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

HRID 478296
Notes
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Reaction equation

HRID 478296 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[CH3:18])[CH:13]=O.[NH2:19]/[C:20](/[CH3:26])=[CH:21]\[C:22]([O:24][CH3:25])=[O:23]>CO>[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[CH3:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 3252872H-pyran-3,5(4H,6H)-dioneHCID 643918Methyl 3-aminocrotonateHCID 8167653-Bromo-4-methylbenzaldehyde

Product 1

HCID 18000988methyl 4-(3-bromo-4-methylphenyl)-2-methyl-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Example 11B (0.34 g, 3.0 mmol), 3-bromo-4-methylbenzaldehyde (Pearson.; Org. Synth. Coll. Vol. V, 1973, 117) (0.60 g, 3.0 mmol) and methyl 3-aminocrotonate (0.35 g, 3.0 mmol) in methanol (8 mL) were heated at 80° C. in a sealed tube for 60 hours. After cooling to ambient temperature, the mixture was filtered and the filter cake washed with methanol and dried to provide the title compound (0.63 g).

Workup

  1. filtrationthe mixture was filtered
  2. washthe filter cake washed with methanol
  3. customdried

Sources & evidence

ORD record
ord-770b9a73c7e049deaa36e09954e4a677
Source dataset
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06642222B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes