Sodium Chloride → 3-[4-(benzyloxy)phenyl]-1-ethyl-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 82633Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 82633
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]3=[N:20][CH:21]=[CH:22][C:23]([CH3:24])=[C:18]3[NH:17][C:16]2=[O:25])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][C:27](C)([O-])C.[K+].C(I)C.[Na+].[Cl-]>CN(C=O)C.O.CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[C:19]3=[N:20][CH:21]=[CH:22][C:23]([CH3:24])=[C:18]3[N:17]([CH2:26][CH3:27])[C:16]2=[O:25])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 5234Sodium ChlorideHCID 6340IodoethaneHCID 23665647Potassium tert-butoxideHCID 585772463-[4-(benzyloxy)phenyl]-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Produkt 1

HCID 585773813-[4-(benzyloxy)phenyl]-1-ethyl-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-oneAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-[4-(benzyloxy)phenyl]-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (86.1 g) in DMF (860 mL) was added potassium tert-butoxide (87.5 g) with cooling in water bath. To the mixture was added ethyl iodide (122 g), and the mixture was stirred at room temperature for 6 h. The mixture was poured into EtOAc (1.2 L) and 5% aq. NaCl (1 L). The organic layer was separated. The aqueous layer was extracted with EtOAc (500 mL). The combined organic phase was washed with brine, dried over MgSO4, passed through a silica gel pad, and evaporated to give 3-[4-(benzyloxy)phenyl]-1-ethyl-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (88 g) as a black solid. This product was subjected to the next reaction without further purification.

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionThe aqueous layer was extracted with EtOAc (500 mL)
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-649459d5c35d4295809ed2aa239c940b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846713B2

Notizen zur Reaktion

Wird geladen…