Butanoic acid, 4-chloro-4-oxo-, ethyl ester → ethyl 4-{7-[5-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl]-1H-indol-3-yl}-4-oxobutanoate

Beteiligte Stoffe

Reaktionsschritte

To a stirred suspension of 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indole (D51) (0.5 g) and ZnCl2 (1.0 g) in DCM (50 mL) was added a solution of ethyl 4-chloro-4-oxobutanoate (2.3 g) in DCM (5 mL) dropwise. After stirring at room temperature overnight, the reaction mixture was washed with water and brine. The organic phase was separated and dried over anhydrous sodium sulphate. Filtration and concentration under vacuum afforded the crude product ethyl 4-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]-4-oxobutanoate (D52) as a brown solid (0.5 g). δH (CDCl3, 400 MHz): 1.27 (3H, t), 1.46 (6H, d), 2.68 (2H, t), 2.83 (2H, t), 3.29 (2H, q), 4.73 (1H, m), 7.07 (1H, d), 7.42 (1H, t), 8.06 (1H, s), 8.08 (1H, dd), 8.16 (1H, dd), 8.26 (1H, dd), 8.56 (1H, d), 10.27 (1H, s). MS (ES): C25H24ClN3O5 requires 481; found 482.2 (M+H+).

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