反応 #2329007

反応方程式

NaHCO3

EtOAc

5-(6-methoxy-1,3-benzoxazol-2-yl)pyridin-2-amine

boron tribromide

→

2-(6-aminopyridin-3-yl)-1,3-benzoxazol-6-ol

収率 116.9%

溶媒

CH2Cl2

CH2Cl2

water

CH2Cl2

反応条件

後処理

1. 1
   workup.ADDITIONAfter full addition the reaction mixture
2. 2
   その他to reach room temperature
3. 3
   workup.STIRRINGstirred at room temperature overnight
4. 4
   温度The reaction mixture was cooled (ice bath)
5. 5
   その他to reach room temperature
6. 6
   workup.STIRRINGstirred vigorously for 10 mins
7. 7
   その他The organic layer was separated
8. 8
   抽出the aqueous layer extracted with CH2Cl2 (3×100 mL)
9. 9
   乾燥the combined organic layers were dried (Na2SO4)
10. 10
    ろ過filtered
11. 11
    その他evaporated

実験手順

To a stirred and cooled (ice bath) solution of 5-(6-methoxy-1,3-benzoxazol-2-yl)pyridin-2-amine (2.07 mmol) in CH2Cl2 (50 mL) was slowly added boron tribromide 1M in CH2Cl2 (4.15 mL) from a pressure equalized dropping funnel. After full addition the reaction mixture was stirred 5 mins in the ice bath, before it was allowed to reach room temperature and then stirred at room temperature overnight. The reaction mixture was cooled (ice bath) and diluted with CH2Cl2 (100 mL), followed by EtOAc (100 mL), water (100 mL) and sat aq NaHCO3 (100 mL) and the resulting mixture allowed to reach room temperature and stirred vigorously for 10 mins. The organic layer was separated and the aqueous layer extracted with CH2Cl2 (3×100 mL), the combined organic layers were dried (Na2SO4), filtered and evaporated to give 0.55 g of 2-(6-aminopyridin-3-yl)-1,3-benzoxazol-6-ol, as a pale yellow foamy solid. MS m/z 228 (M+H).

出典