Hydrochloric Acid → Ethyl 2-(1-(methylsulphonyl)indolin-5-yl)propanoate

참여 물질

반응 단계

5-bromo-1-(methylsulphonyl)indoline (13.4 mmol, 3.7 g) and ethyl-2-chloropropionate (17.4 mmol, 2.38 g) were dissolved in DMF (7 ml) in a protective gas atmosphere at room temperature. Subsequently, manganese (26.8 mmol, 1.47 g), (2,2′-bipyridine) nickel(II)-dibromide (0.938 mmol, 0.351 g) and TFA (0.348 mmol, 27 μl) were added and stirring was carried out at 50° C. for 1.5 h. After cooling the reaction mixture to room temperature, hydrolysis was carried out at room temperature with 1 N HCl (25 ml) and the mixture was extracted with diethyl ether (3×25 ml). The combined organic phases were washed with water (25 ml) and aq. sat. NaCl solution (25 ml) and dried over magnesium sulphate. After removing the solvent in a vacuum and purifying the residue by column chromatography (SiO2, diethyl ether/hexane=3:1), 0.558 g (14% yield) of ethyl 2-(1-(methylsulphonyl)indolin-5-yl)propanoate were obtained.

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