反应 #10195

反应方程式

Potassium iodide

1-(4-Amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone

sodium nitrite

→

1-(4-Iodo-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone

溶剂

H2SO4

H2SO4

H2O

H2O

反应条件

后处理

1. 1
   其他(reaction becomes dark red)
2. 2
   其他The reaction was quenched with NaHSO3 and water (pH 2.5)
3. 3
   萃取then extracted with ethyl acetate (4×30 mL)
4. 4
   干燥After drying (Na2SO4)
5. 5
   过滤the solution was filtered
6. 6
   浓缩concentrated to a yellow oil which
7. 7
   其他was chromatographed on Silica gel
8. 8
   其他to provide a yellow oil
9. 9
   其他above yielded 5 g, 67%)

实验过程

1-(4-Amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (500 mg, 1.85 mmol) was dissolved in H2O (5 mL) and concentrated H2SO4 solution (0.5 mL) then cooled to 0° C. and treated with a solution of sodium nitrite (NaNO2) (140 mg, 2.04 mmol) in H2O (2 mL) dropwise. Potassium iodide (460 mg, 2.78 mmol) in 1N H2SO4 solution (0.5 mL) was added over 10 minutes (reaction becomes dark red). The resulting solution was warmed to room temperature and stirred 18 hours. The reaction was quenched with NaHSO3 and water (pH 2.5) then extracted with ethyl acetate (4×30 mL). After drying (Na2SO4), the solution was filtered and concentrated to a yellow oil which was chromatographed on Silica gel to provide a yellow oil. (260 mg, 37%). (TLC 30% ethyl acetate/hexanes Rf 0.70). (A 5.4 g scale performed as above yielded 5 g, 67%).

来源