Ammonium Chloride → 3-(7-Pyridin-4-yl-pyrazolo[5,1-b]thiazol-6-yl)-phenylamine
Reaktionsgleichung
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:17]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[C:13]3[S:14][CH:15]=[CH:16][N:12]3[N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.[Cl-].[NH4+].C([O-])(O)=O.[Na+]>O1CCOCC1.O.O.[Zn]>[N:21]1[CH:20]=[CH:19][C:18]([C:17]2[C:10]([C:6]3[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=3)=[N:11][N:12]3[CH:16]=[CH:15][S:14][C:13]=23)=[CH:23][CH:22]=1Komponenten
7
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
6-(3-Nitrophenyl)-7-pyridin-4-yl-pyrazolo[5,1-b]thiazole (410 mg, 1.272 mmol) was dissolved in a 3:1 dioxane/water mixture (8 mL). Zinc powder (333 mg, 5.094 mmol, 4 eq) and ammonium chloride (680 mg, 12.72 mmol, 10 eq) were added and the mixture was stirred at 100° C. for 2 hours. It was then diluted with water, made basic by addition of saturated aqueous NaHCO3 and extracted with ethyl acetate (3×20 mL). Combined organic layers were washed with sat. aq. NaHCO3 and brine, dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (DCM/MeOH 97:3) to give 255 mg (68%) of 3-(7-pyridin-4-yl-pyrazolo[5,1-b]thiazol-6-yl)-phenylamine as white solid.
Aufarbeitung
- extractionextracted with ethyl acetate (3×20 mL)
- washCombined organic layers were washed with sat. aq. NaHCO3 and brine
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
- customThe crude product was purified by chromatography on silica gel (DCM/MeOH 97:3)
Quellen und Nachweise
- ORD-Eintrag
- ord-d67425bcdd5e47818c01ea2b655a50cc
- Quelldatensatz
- uspto-grants-2013_09
- Patentnummer
- US08524707B2
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