Reaktion #80289

Reaktionsgleichung

sodium hydroxide

phosphorus oxychloride

N,N-dimethylformamide

benzyl 5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methylindol-4-carboxylate

N,N-dimethylformamide

→

desired compound

Ausbeute 81.5%

Benzyl 5-[(4,6-Dimethoxypyrimidin-2-yl)oxy]-3-formyl-2-methylindol-4-carboxylate

Ausbeute 81.5%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder cooling with ice
2. 2
   workup.ADDITIONthe solution was dropwise added to the above mixture
3. 3
   Temperaturunder cooling with ice
4. 4
   workup.STIRRINGThe mixture was stirred for 30 minutes
5. 5
   Extraktionfor adjustment to pH9, followed by extraction with ethyl acetate
6. 6
   WaschenThe organic layer was washed with water
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   SonstigeThe residue obtained by concentration under reduced pressure
9. 9
   Sonstigewas crystallized from isopropyl ether

Vorschrift

0.46 ml of phosphorus oxychloride was dropwise added to 1.8 ml of N,N-dimethylformamide under cooling with ice, and the mixture was stirred for 30 minutes. Then, 2.3 g of benzyl 5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methylindol-4-carboxylate was dissolved in 10 ml of N,N-dimethylformamide, and the solution was dropwise added to the above mixture under cooling with ice. The mixture was stirred for 30 minutes, and then poured into ice water. An aqueous sodium hydroxide solution was added thereto for adjustment to pH9, followed by extraction with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from isopropyl ether to obtain 2 g (yield: 81.5%) of the desired compound. mp: 148°-149° C.

Quelle