Reacción #2328990

Ecuación de reacción

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

BBr3

NaHCO3

→

title compound

Rendimiento 23.7%

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

Rendimiento 23.7%

Disolventes

dichloromethane

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   OtroThe layers were separated
3. 3
   Extracciónthe aqueous phase was extracted with dichloromethane (4×)
4. 4
   SecadoThe combined organic phases were dried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Otrothe solvents removed in vacuo
7. 7
   OtroThe crude material was purified by preparative HPLC

Procedimiento

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.

Fuente