Reaktion #86253

Reaktionsgleichung

1-(6-bromo-2-pyridyl)-6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridine

tert-butyl 4-oxopiperidine-1-carboxylate

sodium tert-butoxide

tetrahydrofuran

tri-t-butylphosphine

→

desired product

Ausbeute 60.6%

tert-butyl 3-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-4-oxo-piperidine-1-carboxylate

Ausbeute 60.6%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was degassed
2. 2
   Sonstige2 h
3. 3
   SonstigeThe reaction was quenched with water
4. 4
   Extraktionthen extract with EtOAc
5. 5
   TrocknenThe organic layers was dried with sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuum
8. 8
   SonstigeThe crude product was purified by flash chromatography (EtOAc/Heptane eluted @75% EtOAc)

Vorschrift

To a solution of 1-(6-bromo-2-pyridyl)-6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridine (125 mg, 0.340 mmol), tert-butyl 4-oxopiperidine-1-carboxylate (100 mg, 0.51 mmol), palladium acetate (8.0 mg, 0.034 mmol) and sodium tert-butoxide (74 mg, 0.75 mmol) in tetrahydrofuran (8.0 ml, 99 mmol) was added tri-t-butylphosphine (0.020 mL, 0.068 mmol). The mixture was degassed and heat at 48° C. 2 h. The reaction was quenched with water then extract with EtOAc. The organic layers was dried with sodium sulfate, filtered, and concentrated in vacuum. The crude product was purified by flash chromatography (EtOAc/Heptane eluted @75% EtOAc) to give the desired product 100 mg 60% yield. MS (ESI) m/z: 486.1.

Quelle