Reaktion #49616

Reaktionsgleichung

water

LDA heptane THF ethylbenzene

2-Bromo-N-(1-methyl-1-phenylethyl)nicotinamide

DMF

→

4-bromo-1-hydroxy-2-(1-methyl-1-phenylethyl)-1,2-dihydropyrrolo[3,4-c]pyridine-3-one

Ausbeute 25.3%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwarmed from −78° C. to room temperature over 1 hour
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   WaschenThe organic layer was washed with saturated brine
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   SonstigeThe solvent was evaporated under reduced pressure
6. 6
   Sonstigethe residue was purified by flash column chromatography (chloroform/methanol=100/1 to 97/3)

Vorschrift

2-Bromo-N-(1-methyl-1-phenylethyl)nicotinamide (500 mg, 1.57 mmol) was dissolved in THF (20 mL), and the solution was added with LDA-heptane/THF/ethylbenzene solution (2.0 mol/L, 3.5 mL, 7.1 mmol) by drops at −78° C. for 25 minutes under argon atmosphere, followed by stirring at the same temperature for 1.6 hours. Then, the mixture was added with DMF (0.267 mL, 3.45 mmol) and warmed from −78° C. to room temperature over 1 hour. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography (chloroform/methanol=100/1 to 97/3) to obtain 4-bromo-1-hydroxy-2-(1-methyl-1-phenylethyl)-1,2-dihydropyrrolo[3,4-c]pyridine-3-one (138 mg, yield 25%).

Quelle