3-Bromo-4-fluorobenzaldehyde → methyl 4-(3-bromo-4-fluorophenyl)-2,6-dimethyl-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylate

HRID 478305Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 478305
[CH3:1][CH:2]1[C:7](=[O:8])[CH2:6][C:5](=O)[CH2:4][O:3]1.[Br:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[F:19])[CH:14]=O.[NH2:20]/[C:21](/[CH3:27])=[CH:22]\[C:23]([O:25][CH3:26])=[O:24]>C(O)C>[Br:10][C:11]1[CH:12]=[C:13]([CH:14]2[C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]([CH3:27])[NH:20][C:5]3[CH2:4][O:3][CH:2]([CH3:1])[C:7](=[O:8])[C:6]2=3)[CH:16]=[CH:17][C:18]=1[F:19]

Komponenten

5

Edukt 3

HCID 1736043-Bromo-4-fluorobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 234974742-methyl-2H-pyran-3,5(4H,6H)-dione

Produkt 1

HCID 18000971methyl 4-(3-bromo-4-fluorophenyl)-2,6-dimethyl-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The product from Example 84C (1.3 g, 10 mmol), 3-bromo-4-fluorobenzaldehyde (2.4 g, 12 mmol) and methyl 3-aminocrotonate (1.2 g, 10 mmol) in ethanol (10 mL) were heated at 80° C. in a sealed tube for 60 hours. After cooling to ambient temperature, the mixture was filtered and the filtercake washed with ethanol and dried to provide the title compound. The filtrate was concentrated and chromatographed on silica gel eluting with 1% and then 2% and then 5% methanol in dichloromethane to provide additional quantities of the title compound.

Aufarbeitung

  1. filtrationthe mixture was filtered
  2. washthe filtercake washed with ethanol
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e24da46e56ea44a691c6fd45d4528e1a
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642222B2

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