Boron tribromide → 3-(7-Pyridin-4-yl-pyrazolo[5,1-b]thiazol-6-yl)-phenol
Reaktionsgleichung
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[C:12]3[S:13][CH:14]=[CH:15][N:11]3[N:10]=2)[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[N:20]1[CH:19]=[CH:18][C:17]([C:16]2[C:9]([C:5]3[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=3)=[N:10][N:11]3[CH:15]=[CH:14][S:13][C:12]=23)=[CH:22][CH:21]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
6-(3-Methoxy-phenyl)-7-pyridin-4-yl-pyrazolo[5,1-b]thiazole (65 mg, 0.212 mmol) was dissolved in dry DCM (2 mL) and cooled to 0° C. A 1 M solution of boron tribromide in DCM (0.850 mL, 0.848 mmol, 4 eq) was added dropwise and the mixture was allowed to warm to room temperature and stirred for 1 hours. Ice was then added to the reaction mixture, followed by saturated aqueous NaHCO3 until pH 6. The aqueous phase was extracted with DCM and the organic layer was dried and evaporated to dryness. An insoluble solid formed during extraction and it was filtered and combined with the organic layer. The crude product was taken up with toluene and concentrated to dryness three times and the same treatment was repeated with DCM. 50 mg of 3-(7-pyridin-4-yl-pyrazolo[5,1-b]thiazol-6-yl)-phenol (80%) were obtained as pale yellow solid.
Aufarbeitung
- temperatureto warm to room temperature
- additionIce was then added to the reaction mixture
- extractionThe aqueous phase was extracted with DCM
- customthe organic layer was dried
- customevaporated to dryness
- customAn insoluble solid formed during extraction and it
- filtrationwas filtered
- concentrationconcentrated to dryness three times
Quellen und Nachweise
- ORD-Eintrag
- ord-09b308db305d4ac3808ac399b8414822
- Quelldatensatz
- uspto-grants-2013_09
- Patentnummer
- US08524707B2
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