Ammonium Chloride → (+/-)-1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanamine
Reaktionsgleichung
[S:1]([N:11]1[C:19]2[CH:18]=[CH:17][N:16]=[C:15]([C:20](=[N:22]O)[CH3:21])[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[NH4+].[Cl-]>CO.CC(O)=O.[Zn]>[S:1]([N:11]1[C:19]2[CH:18]=[CH:17][N:16]=[C:15]([CH:20]([NH2:22])[CH3:21])[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:3])=[O:2]Komponenten
6
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
A mixture of 1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone oxime (1.29 g, 3.92 mmol), zinc (2.55 g, 39.2 mmol), and NH4Cl (2.10 mg, 39.2 mmol) in MeOH (5 mL) and HOAc (3 mL) was stirred at 80° C. for 4 h. The mixture was cooled to RT and the solid filtered. The filtrate was concentrated under reduced pressure. To the residue was added ammonia solution (50 mL) and the reaction mixture was extracted with DCM (3×50 mL). The combined organic extracts were concentrated under reduced pressure. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH/TEA (15:1:0.2) to afford 1.08 g (87.4%) (±)-1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanamine as a yellow solid: MS (ESI) m/z: 316.2 [M+1]+.
Aufarbeitung
- temperatureThe mixture was cooled to RT
- filtrationthe solid filtered
- concentrationThe filtrate was concentrated under reduced pressure
- additionTo the residue was added ammonia solution (50 mL)
- extractionthe reaction mixture was extracted with DCM (3×50 mL)
- concentrationThe combined organic extracts were concentrated under reduced pressure
- customThe crude product was purified by SiO2 chromatography
- washeluting with DCM/MeOH/TEA (15:1:0.2)
Quellen und Nachweise
- ORD-Eintrag
- ord-69fc62f6eb1344dabe255071613d6ecf
- Quelldatensatz
- uspto-grants-2014_08
- Patentnummer
- US08815877B2
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