Reaktion #45475

Reaktionsgleichung

3-bromo-7-iodothieno[3,2-c]pyridin-4-ylamine

triphenylphosphine

sodium carbonate

acrylonitrile

→

title compound

Ausbeute 88.5%

(2E)-3-(4-amino-3-bromothieno[3,2-c]pyridin-7-yl)acrylonitrile

Ausbeute 88.5%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to ambient temperature
2. 2
   Sonstigesolvents were removed under reduced pressure
3. 3
   SonstigeThe residue was purified by flash chromatography on silica gel

Vorschrift

To a solution of 3-bromo-7-iodothieno[3,2-c]pyridin-4-ylamine (430 mg, 1.21 mmol), triphenylphosphine (128 mg, 0.48 mmol) and sodium carbonate (257 mg, 2.42 mmol) in N,N-dimethylformamide (6 ml) was added acrylonitrile (0.32 ml, 4.84 mmol) followed by palladium(II) acetate (56 mg, 0.24 mmol). The reaction was heated at 77° C. for 18 hours under an atmosphere of nitrogen. The mixture was allowed to cool to ambient temperature and solvents were removed under reduced pressure. The residue was purified by flash chromatography on silica gel using ethyl acetate as the mobile phase to give the title compound (300 mg, 88%) as an off-white solid used directly in the following Suzuki coupling step. LCMS (Conditions g); Rt2.28; MS: MH+ 280.

Quelle