2-Bromopyridine → Methyl 3-(4-fluorophenyl)-2-oxo-2H-1,2'-bipyridine-5-carboxylate

HRID 1909152Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1909152
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](=[O:14])[NH:12][CH:11]=[C:10]([C:15]([O:17][CH3:18])=[O:16])[CH:9]=2)=[CH:4][CH:3]=1.Br[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1.CN[C@H]1[C@H](NC)CCCC1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13](=[O:14])[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[CH:11]=[C:10]([C:15]([O:17][CH3:18])=[O:16])[CH:9]=2)=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 67339481Methyl 5-(4-fluorophenyl)-6-hydroxynicotinate

Produkt 1

HCID 67337652Methyl 3-(4-fluorophenyl)-2-oxo-2H-1,2'-bipyridine-5-carboxylateAusbeute 93,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of methyl 5-(4-fluorophenyl)-6-oxo-1,6-dihydropyridine-3-carboxylate (77.0 mg, 0.31 mmol) in dioxane (2.1 mL) were added 2-bromopyridine (0.15 g, 0.92 mmol), trans-(1R,2R)—N,N′-bismethyl-1,2-cyclohexanediamine (17.7 mg, 0.13 mmol) and potassium carbonate (86.0 mg, 0.62 mmol). The mixture was heated in the microwave reactor at 120° C. for 1 h then heated in an oil bath at 80° C. for 8 h. The mixture was cooled to ambient temperature and dichloromethane was added. The mixture was washed with water, sat. NaHCO3, brine and dried with sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→75% dichloromethane/ethyl acetate) gave the title compound (94 mg). MS 325.1 (M+1).

Aufarbeitung

  1. temperaturethen heated in an oil bath at 80° C. for 8 h
  2. temperatureThe mixture was cooled to ambient temperature
  3. washThe mixture was washed with water, sat. NaHCO3, brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (100% dichloromethane→75% dichloromethane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-8ac49302db134ae4a353644298f28edb
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598209B2

Notizen zur Reaktion

Wird geladen…