تفاعل #45448

معادلة التفاعل

water

suspension

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

N-propargylphthalimide

→

desired product

المردود 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

المردود 43.4%

المذيبات

DMF

triethylamine

ظروف التفاعل

المعالجة

1. 1
   أخرىby bubbling nitrogen through the suspension for 5 minutes
2. 2
   استخلاصextracted with ethyl acetate
3. 3
   غسيلthe combined organic layers were washed with brine
4. 4
   تجفيفdried (Na2SO4)
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated
7. 7
   أخرىThe residue was purified by flash chromatography on silica gel using 3% methanol/dichloromethane

الإجراء التجريبي

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.

المصدر