Reacción #45448

Ecuación de reacción

water

suspension

3-(4-aminophenyl)-7-iodothieno[3,2-c]pyridin-4-amine

N-propargylphthalimide

→

desired product

Rendimiento 43.4%

2-{3-[4-amino-3-(4-aminophenyl)thieno[3,2-c]pyridin-7-yl]prop-2-ynyl}-1H-isoindole-1,3(2H)-dione

Rendimiento 43.4%

Disolventes

DMF

triethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroby bubbling nitrogen through the suspension for 5 minutes
2. 2
   Extracciónextracted with ethyl acetate
3. 3
   Lavadothe combined organic layers were washed with brine
4. 4
   Secadodried (Na2SO4)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe residue was purified by flash chromatography on silica gel using 3% methanol/dichloromethane

Procedimiento

A suspension of Example 77B (0.6 g, 1.63 mmol) in DMF (3 mL) and triethylamine (2 mL) was degassed by bubbling nitrogen through the suspension for 5 minutes, treated with N-propargylphthalimide (0.45 g, 2.45 mmol), PdCl2(PPh3)4 (57 mg, 0.08 mmol), and CuI (15 mg, 0.08 mmol), then heated to 80° C. for 1 hour. The cooled solution was poured into water, extracted with ethyl acetate and the combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography on silica gel using 3% methanol/dichloromethane to provide 300 mg (43% yield) of the desired product.

Fuente