تفاعل #45398

معادلة التفاعل

mixture

7-iodo-3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-4-amine

tert-butyl acrylate

triethylamine

→

desired product

المردود 61.0%

tert-butyl (2E)-3-[4-amino-3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-7-yl]acrylate

المردود 61.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe resulting mixture was cooled to room temperature
2. 2
   أخرىpartitioned between water and ethyl acetate
3. 3
   استخلاصThe organic extract
4. 4
   غسيلwas washed with brine
5. 5
   تجفيفdried (Na2SO4)
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated
8. 8
   أخرىThe residue was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes

الإجراء التجريبي

A mixture of Example 10B (0.417 g, 0.94 mmol), tert-butyl acrylate (0.26 mL, 1.74 mol) and triethylamine (0.7 mL, 5 mmol) in DMF (3 mL) was degassed with nitrogen for 45 minutes, treated with PdCl2(o-tol3P)2 (0.032 g, 0.046 mmol), and heated to 80° C. overnight. The resulting mixture was cooled to room temperature, then partitioned between water and ethyl acetate. The organic extract was washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes to provide 0.25 g (61% yield) of the desired product. MS (ESI(+)) m/e 445 (M+H)+.

المصدر