Tetraethyltin → HCID 21873607, Verbindung

HRID 723530Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 723530
Br[C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[N:10][C:9]2[NH:8][C:7](=[O:16])[CH2:6][S:5][C:4]=2[CH:3]=1.[CH2:17]([Sn](CC)(CC)CC)[CH3:18]>CN(C)C=O.CO.C(OCC)(=O)C.[Pd].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:17]([C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[N:10][C:9]2[NH:8][C:7](=[O:16])[CH2:6][S:5][C:4]=2[CH:3]=1)[CH3:18]

Komponenten

7

Edukt 2

HCID 11704TetraethyltinHCID 21873784Methyl 7-bromo-3,4-dihydro-3-oxo-2H-pyrido[3,2-b]-1,4-thiazine-6-carboxylate

Produkt 1

HCID 21873607HCID 21873607, VerbindungAusbeute 16,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23938PalladiumKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 21584119Ethylacetate methanolLösungsmittel

Versuchsvorschrift

Methyl 7-bromo-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate (Example 304b) (2.00 g, 6.6 mmol), tetraethyltin (3.17 mL, 16 mmol) and bis(triphenylphosphine)palladium(II) chloride (1.12 g, 1.6 mmol) in dimethylformamide (40 mL) were heated at 120° C. for 24 h. The mixture was filtered through Kieselguhr, washed through with ethyl acetate and evaporated. Chromatography on silica gel (20-50% ethyl acetate/petroleum ether) gave a mixture of the 7-ethyl and 7-vinyl compounds (0.29 g). This mixture was hydrogenated in methanol/ethyl acetate (2:1, 60 mL) over 10% palladium on carbon (60 mg) (1 atmosphere, room temperature) for 24 h. Filtration and evaporation of solvent gave the product (0.28 g).

Aufarbeitung

  1. filtrationThe mixture was filtered through Kieselguhr
  2. washwashed through with ethyl acetate
  3. customevaporated
  4. customChromatography on silica gel (20-50% ethyl acetate/petroleum ether) gave
  5. filtrationFiltration and evaporation of solvent

Quellen und Nachweise

ORD-Eintrag
ord-213be68eff2d4c3d9c43a25944fff84c
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141564B2

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