Isopropyl iodide → 3-(Benzyloxy)-5-bromo-1-(propan-2-yl)pyridin-2(1H)-one

HRID 625934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 625934
[CH2:1]([O:8][C:9]1[C:10](=[O:16])[NH:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].I[CH:24]([CH3:26])[CH3:25]>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:10](=[O:16])[N:11]([CH:24]([CH3:26])[CH3:25])[CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 674068463-(benzyloxy)-5-bromopyridin-2(1H)-one

Produkt 1

HCID 674174683-(Benzyloxy)-5-bromo-1-(propan-2-yl)pyridin-2(1H)-oneAusbeute 25,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-(Benzyloxy)-5-bromopyridin-2(1H)-one (200 mg, 0.714 mmol), Cs2CO3 (302 mg, 0.928 mmol), and 2-iodopropane (0.086 mL, 0.857 mmol) were combined in DMF (3 mL) at RT. After stirring overnight the mixture was concentrated. The residue was taken up in CH2Cl2, filtered through a pad of Celite®, and concentrated. Flash column (Biotage-SNAP-10 g, 0-30% EtOAc/hexanes) gave the title compound as a clear oil (58 mg, 25%) which solidified under vacuum. 1H NMR (400 MHz, CDCl3): δ 7.46-7.29 (m, 5 H); 7.05 (d, J=2.4 Hz, 1 H); 6.66 (d, J=2.4 Hz, 1 H); 5.34-5.25 (m, 1 H); 5.09 (s, 2 H); 1.35 (d, J=6.8 Hz, 6 H). LC/MS (M+H)+ 322/324.

Aufarbeitung

  1. concentrationwas concentrated
  2. filtrationfiltered through a pad of Celite®
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ab524c25a8ac40aa82ff67fb86b141e6
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309199B2

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