Reaktion #505903

Reaktionsgleichung

364

2-(3-(3-Chloropropoxy)phenyl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

sodium borohydride

→

365

Ausbeute 55.7%

4-(2-(3-(3-Chloropropoxy)phenyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine

Ausbeute 55.7%

Lösungsmittel

MeOH THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered through celite
2. 2
   Einengenconcentrated
3. 3
   SonstigeThe residue was partitioned between water and dichloromethane
4. 4
   Sonstigethe organic phase was collected
5. 5
   Waschenwashed with brine
6. 6
   Trocknendried (anhydrous MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   SonstigeThe residue was purified by flash chromatography (eluent 90% ethyl acetate/hexanes)

Vorschrift

To the nitro compound 364 (0.84 g, 1.8 mmol) and nickel chloride hexahydrate (0.87 g, 3.7 mmol) in 9:1 MeOH/THF was added sodium borohydride (0.30 g, 7.9 mmol) in small portions. The resulting mixture was stirred at r.t. for 1 h, then filtered through celite and concentrated. The residue was partitioned between water and dichloromethane, the organic phase was collected, washed with brine, dried (anhydrous MgSO4), filtered, and concentrated. The residue was purified by flash chromatography (eluent 90% ethyl acetate/hexanes) to afford 365 (0.43 g, 54% yield). LRMS (M+H): 429.1.

Quelle