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

Reaktionsgleichung

Reaktionsgleichung von HRID 478296
[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]

Komponenten

5

Edukt 3

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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-770b9a73c7e049deaa36e09954e4a677
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642222B2

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