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

HRID 478270

Reaktionsgleichung

Reaktionsgleichung von HRID 478270
[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[F: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[F:18]

Komponenten

5

Edukt 3

HCID 1736043-Bromo-4-fluorobenzaldehydeHCID 3252872H-pyran-3,5(4H,6H)-dioneHCID 643918Methyl 3-aminocrotonate

Produkt 1

HCID 11257964methyl 4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylateAusbeute 50,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of tetrahydropyran-3,5-dione (Terasawa, J. Org. Chem. (1977), 42, 1163-1169) (1.4 g, 12 mmol), 3-bromo-4-fluorobenzaldehyde (3.0 g, 15 mmol), methyl 3-aminocrotonate (1.4 g, 12 mmol) and ethyl alcohol (10 mL) was processed as described in Example 2A. Purification by flash chromatography over silica gel (1% then 2% and then 5% methyl alcohol/methylene chloride) provided the title compound (2.4 g) as a solid.

Aufarbeitung

  1. customPurification by flash chromatography over silica gel (1%

Quellen und Nachweise

ORD-Eintrag
ord-6f069885456a488c9abd175de1e5d856
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642222B2

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