Water → Ethyl 2-[4-chloro-2-fluoro-5-(1-methylethoxy)phenyl]octahydro-1-oxoimidazo[1,5-a]pyridine-3-carboxylate

HRID 263384Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 263384
C(=O)([O-])[O-].[K+].[K+].Br[CH:8](F)[C:9]([O:11][CH2:12][CH3:13])=[O:10].[Cl:15][C:16]1[C:21]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:20][C:19]([NH:26][C:27]([CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][NH:30]2)=[O:28])=[C:18]([F:35])[CH:17]=1.O>C(#N)C.C(OCC)(=O)C>[Cl:15][C:16]1[C:21]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:20][C:19]([N:26]2[C:27](=[O:28])[CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][N:30]3[CH:8]2[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:18]([F:35])[CH:17]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2733407Acetic acid, 2-bromo-2-fluoro-, ethyl esterHCID 19037321N-[4-Chloro-2-fluoro-5-(1-methylethoxy)phenyl]piperidine-2-carboxamide

Produkt 1

HCID 19037326Ethyl 2-[4-chloro-2-fluoro-5-(1-methylethoxy)phenyl]octahydro-1-oxoimidazo[1,5-a]pyridine-3-carboxylateAusbeute 21,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of potassium carbonate (724 mg, 5.24 mmol), ethyl bromofluoroacetate (882 mg, 4.76 mmol) and the product of Step A (1.5 g, 4.76 mmol) in acetonitrile (50 mL) was heated at reflux overnight. 100 mL of H2O and 200 mL of ethyl acetate were added to the mixture. The organic layer was separated, dried (MgSO4), filtered, and evaporated under vacuum to dryness. Flash chromatography yielded the title compound of Step B as a white solid (400 mg) m.p. 83°-85° C. 1H NMR δ7.21 (d,1H), 7.18 (d,1H), 4.92 (s,1H), 4.50 (m,1H), 4.16-4.09 (m,2H), 3.29 (m,1H), 2.95 (m,1H), 2.50 (m,1H), 2.10 (m,1H), 1.96 (m,1H), 1.80-1.58 (m,2H), 1.37 (d,6H), 1.35 (t,3H).

Aufarbeitung

  1. temperatureat reflux overnight
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under vacuum to dryness

Quellen und Nachweise

ORD-Eintrag
ord-9dc2de2cdd334059be8b20ecf8b907cd
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05643855

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