Reaktion #45398

Reaktionsgleichung

mixture

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

tert-butyl acrylate

triethylamine

→

desired product

Ausbeute 61.0%

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

Ausbeute 61.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting mixture was cooled to room temperature
2. 2
   Sonstigepartitioned between water and ethyl acetate
3. 3
   ExtraktionThe organic extract
4. 4
   Waschenwas washed with brine
5. 5
   Trocknendried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe residue was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes

Vorschrift

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)+.

Quelle