Acetic Acid → ethyl N-{2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]ethyl}-beta-alaninate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of [7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]acetaldehyde (D88) (25 mg), ethyl β-alaninate (14 mg) and acetic acid (0.1 mL) in DCM (5 mL) was added sodium triacetoxyborohydride (26 mg). The reaction was stirred at 20° C. for 2 h. The reaction mixture was partitioned between DCM (25 mL) and water (25 mL). The organic phase was washed with brine (25 mL), and evaporated to afford the crude product ethyl N-{2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]ethyl}-β-alaninate (D90) (30 mg), which was used directly in the next step. MS (ES): C27H31ClN4O4 requires 510; found 511.2 (M+H+).

Provenance & Evidence