Reaktion #45448

Reaktionsgleichung

water

suspension

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

N-propargylphthalimide

→

desired product

Ausbeute 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

Ausbeute 43.4%

Lösungsmittel

DMF

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeby bubbling nitrogen through the suspension for 5 minutes
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   Waschenthe combined organic layers were washed with brine
4. 4
   Trocknendried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was purified by flash chromatography on silica gel using 3% methanol/dichloromethane

Vorschrift

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.

Quelle