Pyruvic Acid → HCID 90039786, Verbindung

HRID 526007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 526007
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=O.N12CCN(CC1)CC2.[NH2:15][C:16]1[C:25](I)=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([CH3:27])[N:17]=1>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:23][O:22][C:20]([C:19]1[CH:24]=[C:25]2[CH:4]=[C:2]([C:1]([OH:6])=[O:5])[NH:15][C:16]2=[N:17][C:18]=1[CH3:27])=[O:21]

Komponenten

6

Edukt 3

HCID 1060Pyruvic AcidHCID 9237DabcoHCID 59747893Methyl 6-amino-5-iodo-2-methylnicotinate

Produkt 1

HCID 90039786HCID 90039786, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Under argon, pyruvic acid (6.90 ml, 100.1 mmol) and 1,4-diazabicyclo[2.2.2]octane (11.2 g, 100.1 mmol) were added to a solution of methyl 6-amino-5-iodo-2-methylnicotinate (9.00 g, 30.8 mmol) in N,N-dimethylformamide (88 ml), and the flask was evacuated and flushed with argon. Argon was subsequently passed through the solution for 5 min, palladium(II) acetate (0.345 g, 1.54 mmol) was then added and the mixture was heated at 100° C. for 2 h. The cooled solution was filtered through Celite and the dimethylformamide was distilled off. The residue was then taken up in water and acidified with hydrochloric acid, giving a solid (6.3 g, 86% of theory). HPLC-MS: log P=1.26; mass (m/z): 235.0 (M+H)+; 1H-NMR (DMSO) 2.79 (s, 3H), 3.85 (s, 3H), 7.19 (s, 1H), 8.62 (s, 1H), 12.50 (s, 1H).

Aufarbeitung

  1. customthe flask was evacuated
  2. customflushed with argon
  3. filtrationThe cooled solution was filtered through Celite
  4. distillationthe dimethylformamide was distilled off
  5. customgiving a solid (6.3 g, 86% of theory)

Quellen und Nachweise

ORD-Eintrag
ord-9a619e9f2d914363960361d9b17d6462
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345247B2

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