Bromomethylcyclopropane → 5-Bromo-1-(cyclopropylmethyl)-1,2-dihydropyridin-2-one

HRID 518259

Reaktionsgleichung

Reaktionsgleichung von HRID 518259
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.[CH3:9][C:10]([CH3:13])([O-])[CH3:11].[K+].BrCC1CC1>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([CH2:9][CH:10]2[CH2:13][CH2:11]2)[CH:7]=1

Komponenten

6

Edukt 3

HCID 81503BromomethylcyclopropaneHCID 23665647Potassium tert-butoxideHCID 178515818HCID 178515818, Verbindung

Produkt 1

HCID 596357015-Bromo-1-(cyclopropylmethyl)-1,2-dihydropyridin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 5-bromopyridin-2-ol (1.0 g, 5.75 mmol) in DMF (10 mL) at RT, potassium tert-butoxide (0.68 g, 6.07 mmol) was added and the mixture was stirred for 30 min. To this mixture, (bromomethyl)cyclopropane (1.03 g, 8.62 mmol) was added, and the resulting mixture was stirred at 70° C. for 2 h. The mixture was allowed to cool to RT, diluted with EtOAc (50 mL) and quenched with water (20 mL). The organic layer was washed with water (2×20 mL) and brine (20 mL), dried over anhydrous MgSO4 and filtered. The filtrate was concentrated in vacuo to afford 5-bromo-1-(cyclopropylmethyl)pyridin-2(1H)-one.

Aufarbeitung

  1. stirringthe resulting mixture was stirred at 70° C. for 2 h
  2. customquenched with water (20 mL)
  3. washThe organic layer was washed with water (2×20 mL) and brine (20 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8da7c754576248148ca49936b4896902
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115141B2

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