Reaktion #491346

Reaktionsgleichung

NaH

II

(4-Benzyloxy-pyridin-2-yl)-pyridin-2-yl-amine

Na2S2O3

ethyl 7-bromoheptanoate

→

III

Ausbeute 48.0%

7-[(4-Benzyloxy-pyridin-2-yl)-pyridin-2-yl-amino]-heptanoic acid ethyl ester

Ausbeute 48.0%

Lösungsmittel

DMF

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe phases were separated
2. 2
   WaschenThe organic phase was washed with brine (100 mL)
3. 3
   Trocknendried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Sonstigesubsequently evaporated under reduced pressure
6. 6
   SonstigeThe resulting residue was purified by silica gel column chromatography
7. 7
   Wascheneluting with hexane/EtOAc (90:10 to 70:30)

Vorschrift

NaH (245 mg, 6.38 mmol) was added to II (1.77 g, 6.38 mmol) in DMF (25 mL) at rt. After 15 min, KI (1.588 g, 9.57 mmol) and ethyl 7-bromoheptanoate (1.86 mL, 9.57 mmol) were added, and the reaction mixture was stirred at 90° C. for 17 h. Aqueous 0.1 M Na2S2O3 (100 mL) and EtOAc (100 mL) were added and the phases were separated. The organic phase was washed with brine (100 mL), dried over MgSO4, filtered, and subsequently evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography eluting with hexane/EtOAc (90:10 to 70:30) to furnish III as a yellow oil (1.321 g, 48%).

Quelle