Reaktion #48979

Reaktionsgleichung

Sodium hydride

4-amino-3-(2-(benzyloxy)ethyl)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

3,4,5-trichloropyridine

→

3-(2-(benzyloxy)ethyl)-8-(cyclopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one

Lösungsmittel

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to rt
2. 2
   Sonstigequenched with drops of water
3. 3
   workup.ADDITIONpoured into 0.5M KH2PO4 (15 mL)
4. 4
   Extraktionextracted with ethyl acetate (50 mL×2)
5. 5
   WaschenThe combined extracts were washed with brine (50 mL)
6. 6
   Sonstigedried
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   Sonstigepurified by silica gel chromatography (ethyl acetate:petroleum ether)

Vorschrift

Sodium hydride (230 mg, 60%, 5.8 mmol) was added portionwise to a solution of 4-amino-3-(2-(benzyloxy)ethyl)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one (800 mg, 1.86 mmol) and DMSO (20 mL). After 10 min at rt, 3,4,5-trichloropyridine (1.0 g, 5.47 mmol) was added. The reaction was then heated at 50° C. overnight, allowed to cool to rt, quenched with drops of water, poured into 0.5M KH2PO4 (15 mL), and then extracted with ethyl acetate (50 mL×2). The combined extracts were washed with brine (50 mL), dried, filtered, concentrated, and purified by silica gel chromatography (ethyl acetate:petroleum ether) to give 3-(2-(benzyloxy)ethyl)-8-(cyclopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one.

Quelle