Reaktion #1491778

Reaktionsgleichung

water

tert-butyl 4-(4-{6-[(E)-2-(dimethylamino)ethenyl]-5-nitropyridin-3-yl}-1H-pyrazol-1-yl)piperidine-1-carboxylate

SnCl2.2H2O

→

tert-butyl 4-[4-(1-hydroxy-1H-pyrrolo[3,2-b]pyridin-6-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

Ausbeute 54.0%

Lösungsmittel

EtOAc

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigelayers were separated
2. 2
   ExtraktionThe aqueous layer was extracted with EtOAc
3. 3
   Waschenwashed with sat. NH4Cl and brine
4. 4
   SonstigeAfter evaporation
5. 5
   Sonstigethe crude product was chromatographed (Mesh/DCM 1:20)
6. 6
   Sonstigeto give a yellow solid, 170 mg

Vorschrift

tert-butyl 4-(4-{6-[(E)-2-(dimethylamino)ethenyl]-5-nitropyridin-3-yl}-1H-pyrazol-1-yl)piperidine-1-carboxylate (366 mg, 0.81 mmol) and SnCl2.2H2O (966 mg, 4.26 mmol, 5.0 eq) in 3 ml of EtOAc were stirred at r.t. for 2 hours. EtOAc and water were added and layers were separated. The aqueous layer was extracted with EtOAc, washed with sat. NH4Cl and brine. After evaporation, the crude product was chromatographed (Mesh/DCM 1:20) to give a yellow solid, 170 mg, in 54% yield.

Quelle