Reacción #10195

Ecuación de reacción

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

Disolventes

H2SO4

H2SO4

H2O

H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   Otro(reaction becomes dark red)
2. 2
   OtroThe reaction was quenched with NaHSO3 and water (pH 2.5)
3. 3
   Extracciónthen extracted with ethyl acetate (4×30 mL)
4. 4
   SecadoAfter drying (Na2SO4)
5. 5
   Filtraciónthe solution was filtered
6. 6
   Concentraciónconcentrated to a yellow oil which
7. 7
   Otrowas chromatographed on Silica gel
8. 8
   Otroto provide a yellow oil
9. 9
   Otroabove yielded 5 g, 67%)

Procedimiento

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%).

Fuente