Reaktion #309984

ord-1037bf22bf5942f0a73a46fefb548d40

Reaktionsgleichung

Cc1cc(=O)n(-c2ccccc2)c(C)c1C(=O)N[C@H](c1cccc(F)c1)C1CCC1
2,4-dimethyl-6-oxo-1-phenyl-1,6-dihydro-pyridine-3-carboxylic acid [(S)-cyclobutyl-(3-fluoro-phenyl)-methyl]-amide
F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2
selectfluor
Cc1c(C(=O)N[C@H](c2cccc(F)c2)C2CCC2)c(C)n(-c2ccccc2)c(=O)c1F
crude title product
Ausbeute 19.0%
Cc1c(C(=O)N[C@H](c2cccc(F)c2)C2CCC2)c(C)n(-c2ccccc2)c(=O)c1F
5-Fluoro-2,4-dimethyl-6-oxo-1-phenyl-1,6-dihydro-pyridine-3-carboxylic acid [(S)-cyclobutyl-(3-fluoro-phenyl)-methyl]-amide
Ausbeute 19.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigewas sonicated for 3 hrs at 40° C.
  2. 2
    SonstigeIt was quenched with water (3 ml)
  3. 3
    Extraktionextracted with ethyl acetate (3×1 mL)
  4. 4
    Wascheneluted with ethyl acetate

Vorschrift

A suspension of 2,4-dimethyl-6-oxo-1-phenyl-1,6-dihydro-pyridine-3-carboxylic acid [(S)-cyclobutyl-(3-fluoro-phenyl)-methyl]-amide (9.91 mg, 0.0245 mmol and selectfluor (10.0 mg, 0.0282 mmol) in acetonitrile (0.1 mL) was sonicated for 3 hrs at 40° C. then allowed to stand for 3 days. It was quenched with water (3 ml) and extracted with ethyl acetate (3×1 mL). The combined organic solution was transferred to a preparative TLC plate (SiO2, 0.25 mm×20 cm×20 cm) and eluted with ethyl acetate to give the crude title product (4 mg, 19% yield). LC-MS (m/z) 423.2 (MH+); tR=1.44.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08207347B2uspto-grants-2012_06