Sodium periodate → tert-butyl 5-oxo-3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

HRID 1896933Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1896933
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[N:5][C:6]2[CH2:7][CH2:8][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][C:11]=2[CH:12]=1.I([O-])(=O)(=O)=[O:23].[Na+]>C(Cl)(Cl)(Cl)Cl.CC#N.O.C(Cl)Cl.O.[Ru](Cl)(Cl)Cl>[O:23]=[C:10]1[N:9]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:8][CH2:7][C:6]2[N:5]=[CH:4][C:3]([C:2]([F:20])([F:1])[F:21])=[CH:12][C:11]1=2

Komponenten

7

Edukt 2

HCID 23667635Sodium periodateHCID 58885211tert-Butyl 3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

Produkt 1

HCID 58562753tert-butyl 5-oxo-3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6093376Ruthenium trichloride hydrateKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 18669661Acetonitrile tetrachloromethaneLösungsmittel

Versuchsvorschrift

Into a 250 mL round-bottom flask, was placed a solution of tert-butyl 3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (as prepared in the previous step, 3.84 g, 0.01 mol, 1.00 equiv) in CCl4/CH3CN=10/1 (66 mL), a solution of sodium periodate (8.135 g, 38.01 mmol, 3.00 equiv) in water (20 mL) and Ruthenium(III)Chloride Hydrate (0.992 g, 0.30 equiv). The resulting solution was stirred for 12 h at room temperature, and then the mixture was diluted with 50 mL of CH2Cl2. The solids were filtered out. The filtrate was concentrated under vacuum. The residue was purified by chromatography over a silica gel column with ethyl acetate/petroleum ether (1:50-1:10). The title compound was obtained as a white solid.

Aufarbeitung

  1. customInto a 250 mL round-bottom flask, was placed
  2. filtrationThe solids were filtered out
  3. concentrationThe filtrate was concentrated under vacuum
  4. customThe residue was purified by chromatography over a silica gel column with ethyl acetate/petroleum ether (1:50-1:10)

Quellen und Nachweise

ORD-Eintrag
ord-be0d039d648e43dca289cc6174d70135
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518969B2

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