Reaktion #7836

Reaktionsgleichung

3-chloro-4-(cyanomethyl)-N-(3-hydroxypyridin-2-yl)benzamide

→

(2-chloro-4-[1,3]oxazolo[4,5-b]pyridin-2-ylphenyl)acetonitrile

Lösungsmittel

POCl3

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeExcess POCl3 was removed by distillation
2. 2
   workup.ADDITIONThe crude mixture was diluted with H2O
3. 3
   Extraktionextracted with CH2Cl2 (3×20 mL)
4. 4
   Sonstigepurified by automated flash chromatography

Vorschrift

3-chloro-4-(cyanomethyl)-N-(3-hydroxypyridin-2-yl)benzamide (550 mg, 1.9 mmol) was refluxed in POCl3 (15 mL) for 2.5 h. Excess POCl3 was removed by distillation and the mixture was cooled to rt. The crude mixture was diluted with H2O. The aqueous layer was made basic (pH 14) with 1N NaOH and extracted with CH2Cl2 (3×20 mL). The residue was adsorbed onto silica gel and purified by automated flash chromatography using an EtOAc/hexane gradient to afford (2-chloro-4-[1,3]oxazolo[4,5-b]pyridin-2-ylphenyl)acetonitrile as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 8.65–8.63 (d, 1H), 8.41 (s, 1H), 8.30–8.27 (d, 1H), 7.93–7.90 (d, 2H), 7.77–7.74 (d, 2H), 7.38–7.34 (m, 2H) 3.95 (s, 2H). MS (ESI) 270 (M+H)+.

Quelle