2,2'-Bipyridine → 4-Bromo-1-cyclopropylpyridin-2(1H)-one

HRID 406735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 406735
[Br:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.[CH:9]1(B(O)O)[CH2:11][CH2:10]1.N1C=CC=CC=1C1C=CC=CN=1.C([O-])([O-])=O.[Na+].[Na+].[NH4+].[Cl-]>CC([O-])=O.CC([O-])=O.[Cu+2].ClCCCl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]([CH:9]2[CH2:11][CH2:10]2)[C:4](=[O:8])[CH:3]=1

Komponenten

8

Edukt 5

HCID 14742,2'-BipyridineHCID 10340Sodium Carbonate2×HCID 25517Ammonium ChlorideHCID 8171154-Bromo-2-hydroxypyridineHCID 2760897Cyclopropylboronic acid2×

Produkt 1

HCID 596356474-Bromo-1-cyclopropylpyridin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

A flask charged with a stir bar, 4-bromo-1H-pyridin-2-one (1.80 g), cyclopropylboronic acid (2.00 g), Cu(OAc)2 (2.00 g), 2,2′-bipyridine (1.70 g), Na2CO3 (2.47 g), and 1,2-dichloroethane (75 mL) was heated to 70° C. and the mixture was stirred at this temperature in air overnight. Then, another portion of cyclopropylboronic acid (0.50 g) and Na2CO3 (0.55 g) were added and the mixture was further stirred at reflux temperature for another 4 h. After cooling to ambient temperature, aqueous NH4Cl solution was added and the resultant mixture was extracted with dichloromethane. The combined organic extracts were dried (MgSO4) and the solvent was evaporated. The residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate 50:50->35:65) to afford the title compound as an oil that crystallized on standing. Yield: 0.82 g (37% of theory); Mass spectrum (ESI+): m/z=214/216 (Br) [M+H]+.

Aufarbeitung

  1. additionA flask charged with a stir bar
  2. stirringthe mixture was further stirred
  3. temperatureat reflux temperature for another 4 h
  4. extractionthe resultant mixture was extracted with dichloromethane
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. customthe solvent was evaporated
  7. customThe residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate 50:50->35:65)

Quellen und Nachweise

ORD-Eintrag
ord-a7b635cc3f734059ad6181429b66d4da
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754076B2

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