Reaktion #1491791

Reaktionsgleichung

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

NaH

NH2Cl

thiosulfate

ammonium chloride

→

solid

Ausbeute 45.0%

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

Ausbeute 45.0%

Lösungsmittel

DMF

Et2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITION2004, 1371: ˜0.15 M, 16 ml) was added
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   EinengenThe organic layer was concentrated
4. 4
   Sonstigethe product was purified by column chromatography (EtOAc:MeOH=100:5)

Vorschrift

To a solution of tert-butyl 4-[4-(1H-pyrrolo[3,2-b]pyridin-6-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate: (0.73 g, 2.0 mmol) in 4.0 mL of DMF at −20° C. was added NaH (60% in oil, 96 mg, 2.4 mmol) in one portion. After 15 min, the mixture was stirred at room temperature for 30 min. A solution of NH2Cl in Et2O (prepared according to the procedure described in J. Org. Chem. 2004, 1371: ˜0.15 M, 16 ml) was added. The mixture was poured into a saturated solution of thiosulfate and ammonium chloride, and extracted with ethyl acetate. The organic layer was concentrated and the product was purified by column chromatography (EtOAc:MeOH=100:5). The entitled intermediate was isolated as a light brown solid (350 mg, 45% yield) (starting material (220 mg) was also recovered).

Quelle