Réaction #45448

Équation de réaction

water

suspension

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

N-propargylphthalimide

→

desired product

Rendement 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

Rendement 43.4%

Solvants

DMF

triethylamine

Conditions de réaction

Traitement

1. 1
   Autreby bubbling nitrogen through the suspension for 5 minutes
2. 2
   Extractionextracted with ethyl acetate
3. 3
   Lavagethe combined organic layers were washed with brine
4. 4
   Séchagedried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   AutreThe residue was purified by flash chromatography on silica gel using 3% methanol/dichloromethane

Mode opératoire

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.

Source