Cesium carbonate → 3-[[3,5,6-Trifluoro-4-[(2,2-dimethyldioxolan-4-yl)methoxy]pyridin-2-yl]oxy]-4-(benzyloxy)benzonitrile

HRID 1267090Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1267090
F[C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH:11]2[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12]2)[C:5]([F:18])=[C:4]([F:19])[N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[OH:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:30]#[N:31]>CC#N>[F:8][C:7]1[C:2]([O:26][C:27]2[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=2[O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:30]#[N:31])=[N:3][C:4]([F:19])=[C:5]([F:18])[C:6]=1[O:9][CH2:10][CH:11]1[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12]1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 154534514-(Benzyloxy)-3-hydroxybenzonitrileHCID 234422212,3,5,6-Tetrafluoro-4-[(2,2-dimethyldioxolan-4-yl)methoxy]pyridine

Produkt 1

HCID 695506003-[[3,5,6-Trifluoro-4-[(2,2-dimethyldioxolan-4-yl)methoxy]pyridin-2-yl]oxy]-4-(benzyloxy)benzonitrileAusbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To 2,3,5,6-tetrafluoro-4-[(2,2-dimethyidioxolan-4-yl)methoxy]pyridine (3.2 g, 11 mmol) in CH3CN (20 mL) was added Cs2CO3 (3.8 g, 12 mmol) and 3-hydroxy-4-(benzyloxy)benzonitrile (2.5 g, 11 mmol). After stirring for 24 hours the reaction was partitioned with water and ethyl acetate. The layers were separated, washed with water and brine, dried (Na2SO4), and the solvent was removed in vacuo. The residue was triturated with hexane/ethyl acetate (1/1) and the resulting solid was collected by filtration to give 3-[[3,5,6-trifluoro-4-[(2,2-dimethyldioxolan-4-yl)methoxy]pyridin-2-yl]oxy]-4-(benzyloxy)benzonitrile (3.0 g).

Aufarbeitung

  1. customwas partitioned with water and ethyl acetate
  2. customThe layers were separated
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was removed in vacuo
  6. customThe residue was triturated with hexane/ethyl acetate (1/1)
  7. filtrationthe resulting solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-08dd5f32aeb5401d8c1c78a7a8fcaec3
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06552030B2

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