反応 #2328990

反応方程式

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

BBr3

NaHCO3

→

title compound

収率 23.7%

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

収率 23.7%

溶媒

dichloromethane

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   その他The layers were separated
3. 3
   抽出the aqueous phase was extracted with dichloromethane (4×)
4. 4
   乾燥The combined organic phases were dried (MgSO4)
5. 5
   ろ過filtered
6. 6
   その他the solvents removed in vacuo
7. 7
   その他The crude material was purified by preparative HPLC

実験手順

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.

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