Boron tribromide → 2-[6-(Dimethylamino)pyridin-3-yl]-1,3-benzoxazol-5-ol
Reaktionsgleichung
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]3[CH:12]=[CH:13][C:14]([N:17]([CH3:19])[CH3:18])=[N:15][CH:16]=3)=[N:8][C:7]=2[CH:20]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>ClCCl>[CH3:18][N:17]([CH3:19])[C:14]1[N:15]=[CH:16][C:11]([C:9]2[O:10][C:6]3[CH:5]=[CH:4][C:3]([OH:2])=[CH:20][C:7]=3[N:8]=2)=[CH:12][CH:13]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of 5-(5-methoxy-1,3-benzoxazol-2-yl)-N,N-dimethylpyridin-2-amine (0.368 mmol) in dichloromethane (2.0 mL) was added BBr3 in dichloromethane (1.84 mmol) at 0° C. under an atmosphere of argon and the reaction stirred for 1 h at 0° C. The reaction mixture was neutralized with NaHCO3 (sat. aq.) and dichloromethane was added. The layers were separated and the aqueous phase was extracted with dichloromethane (4×). The combined organic phases were dried (MgSO4), filtered and the solvents removed in vacuo. The crude material was purified by preparative HPLC to give 22.3 mg of the title compound as a white solid. 1H NMR δ ppm 9.44 (s, 1H), 8.83 (d, 1H), 8.13 (dd, 1H), 7.48 (d, 1H), 7.01 (d, 1H), 6.80 (d, 1H), 6.76 (dd, 1H), 3.14 (s, 6H). MS m/z (M+H) 256.
Aufarbeitung
- additionwas added
- customThe layers were separated
- extractionthe aqueous phase was extracted with dichloromethane (4×)
- dry with materialThe combined organic phases were dried (MgSO4)
- filtrationfiltered
- customthe solvents removed in vacuo
- customThe crude material was purified by preparative HPLC
Quellen und Nachweise
- ORD-Eintrag
- ord-52538839318447f79a7015f49c633089
- Quelldatensatz
- uspto-grants-2010_03
- Patentnummer
- US07670591B2
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