Reaktion #2328990

Reaktionsgleichung

5-(5-methoxy-1,3-benzoxazol-2-yl)-N,N-dimethylpyridin-2-amine

BBr3

NaHCO3

→

title compound

Ausbeute 23.7%

2-[6-(Dimethylamino)pyridin-3-yl]-1,3-benzoxazol-5-ol

Ausbeute 23.7%

Lösungsmittel

dichloromethane

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   SonstigeThe layers were separated
3. 3
   Extraktionthe aqueous phase was extracted with dichloromethane (4×)
4. 4
   TrocknenThe combined organic phases were dried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Sonstigethe solvents removed in vacuo
7. 7
   SonstigeThe crude material was purified by preparative HPLC

Vorschrift

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.

Quelle