Reaktion #2057558

Reaktionsgleichung

8-(pyridin-3-yl)-1H-chromeno[3,2-c]pyridine-1,10(2H)-dione

methylmagnesium bromide

pyridinium p-toluenesulfonate

→

10-methylene-8-(pyridin-3-yl)-2,10-dihydro-1H-chromeno[3,2-c]pyridin-1-one

Lösungsmittel

THF

1,2-dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was quenched at 0° C. with saturated aqueous ammonium chloride solution
2. 2
   workup.ADDITIONdiluted with ethyl acetate
3. 3
   SonstigeThe aqueous phase was separated
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   WaschenThe combined organic phases were washed with brine
6. 6
   Trocknendried over anhydrous sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   Sonstigeto afford a tan solid
10. 10
    Temperaturthe mixture was heated
11. 11
    Temperaturat reflux for 2 h
12. 12
    Sonstigeto afford a tan suspension
13. 13
    FiltrationThis mixture was filtered
14. 14
    Waschenthe solids were washed with 1,2 dichloroethane
15. 15
    Sonstigedried

Vorschrift

A solution of 8-(pyridin-3-yl)-1H-chromeno[3,2-c]pyridine-1,10(2H)-dione (0.100 g, 0.345 mmol) in THF (3.00 mL) was cooled to 0° C. and methylmagnesium bromide (3.0 M in diethyl ether) (0.345 mL, 1.034 mmol) was added dropwise. The mixture stirred at 0° C. for 1 h. The mixture was quenched at 0° C. with saturated aqueous ammonium chloride solution and diluted with ethyl acetate. The aqueous phase was separated and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a tan solid. The material was dissolved in 1,2-dichloroethane (3.00 mL), pyridinium p-toluenesulfonate (8.66 mg, 0.034 mmol) was added, and the mixture was heated at reflux for 2 h to afford a tan suspension. This mixture was filtered, and the solids were washed with 1,2 dichloroethane and dried to afford 10-methylene-8-(pyridin-3-yl)-2,10-dihydro-1H-chromeno[3,2-c]pyridin-1-one as a tan solid. MS m/z=289.0 [M+H]+. Calcd for C18H12N2O2: 288.1.

Quelle