Reaktion #6332

Reaktionsgleichung

N-[(7-Bromo-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide

N-[(7-bromo-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide

phenylboronic acid

sodium carbonate

→

title compound

N-[(7-phenyl-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide

Lösungsmittel

tetrahydrofuran

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture is warmed for 15.5 hours in an oil bath at 68°
2. 2
   SonstigeThe mixture is then partitioned between aqueous sodium carbonate (2M, 2 ml) and methylene chloride (3 ml)
3. 3
   SonstigeAfter separation of the layers
4. 4
   Extraktionthe aqueous phase is extracted with additional methylene chloride (3×2 ml)
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Einengenconcentrated
7. 7
   Sonstigeto provide a solid
8. 8
   Wascheneluted with ethyl acetate/methanol gradient
9. 9
   Einengenconcentrated

Vorschrift

(±) (1S,9aS/1R,9aR) N-[(7-Bromo-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide (EXAMPLE 24, 129 mg) is dissolved in tetrahydrofuran (1 ml). To this mixture palladium tetrakis(triphenylphosphine) (22 mg), phenylboronic acid (61 mg) and aqueous sodium carbonate (2M, 0.45 ml) is added. The mixture is warmed for 15.5 hours in an oil bath at 68°. The mixture is then partitioned between aqueous sodium carbonate (2M, 2 ml) and methylene chloride (3 ml). After separation of the layers, the aqueous phase is extracted with additional methylene chloride (3×2 ml). The organic layers are combined, dried over magnesium sulfate and concentrated to provide a solid. This solid is taken up in methylene chloride and placed on a 20.5 cm×2.5 cm, 40-63μ silica column and eluted with ethyl acetate/methanol gradient. The appropriate fractions are pooled and concentrated to give the title compound, mp 181°-183°; NMR (CDCl3, 300 MHz) 7.43, 6.08, 4.53, 4.54, 3.83, 3.70, 3.35, 3.17 and 2.07 δ.

Quelle