반응 #45448

반응 방정식

water

suspension

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

N-propargylphthalimide

→

desired product

수율 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

수율 43.4%

용매

DMF

triethylamine

반응 조건

후처리

1. 1
   기타by bubbling nitrogen through the suspension for 5 minutes
2. 2
   추출extracted with ethyl acetate
3. 3
   세척the combined organic layers were washed with brine
4. 4
   건조dried (Na2SO4)
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The residue was purified by flash chromatography on silica gel using 3% methanol/dichloromethane

실험 절차

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.

출처