Réaction #2328990

Équation de réaction

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

BBr3

NaHCO3

→

title compound

Rendement 23.7%

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

Rendement 23.7%

Solvants

dichloromethane

dichloromethane

dichloromethane

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source