Reaction #2328990

Reaction equation

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

BBr3

NaHCO3

→

title compound

Yield 23.7%

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

Yield 23.7%

Solvents

dichloromethane

dichloromethane

dichloromethane

Conditions

Workup

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

Procedure

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