Reacción #1518117

Ecuación de reacción

3-iodo-5-nitro-1H-indazole

copper (I) cyanide

→

5-nitro-1H-indazole-3-carbonitrile

Rendimiento 20.3%

Disolventes

EtOAc

NMP

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to rt
2. 2
   Filtraciónfiltered through celite
3. 3
   Lavadorinsing with EtOAc
4. 4
   LavadoThe filtrate was washed 2× with water and 2× with brine
5. 5
   SecadoThe organic layer was dried over Na2SO4
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated
8. 8
   OtroThe crude material was purified by flash column chromatography
9. 9
   Lavadoeluting with 0%-50% EtOAc/Hex

Procedimiento

3-iodo-5-nitro-1H-indazole (6.9 g, 23.87 mmol) was taken up in NMP (90 mL) and copper (I) cyanide (4.28 g, 47.7 mmol) was added. The reaction was heated at 160° C. for 1 h, then cooled to rt. The reaction mixture was diluted with EtOAc and filtered through celite, rinsing with EtOAc. The filtrate was washed 2× with water and 2× with brine. The organic layer was dried over Na2SO4, filtered, and concentrated. The crude material was purified by flash column chromatography eluting with 0%-50% EtOAc/Hex. 0.91 g of 5-nitro-1H-indazole-3-carbonitrile was obtained.

Fuente